Alkanes and Fuels

Сайт: Young Education
Курс: Organic Chemistry
Книга: Alkanes and Fuels
Надруковано: ゲストユーザ
Дата: понеділок 5 жовтня 2026 03:04 AM

1. The Alkane Family

Learning outcomes
  • I can define alkanes as saturated hydrocarbons.
  • I can explain the meaning of a saturated compound.
  • I can identify alkanes from their molecular formulas.
  • I can recognize the general formula of alkanes.
  • I can describe the bonding present in alkane molecules.

https://images.openai.com/static-rsc-4/wUn_lKxEtAguE4yyb6qzmubALb0dELeW8rwmJglIme_-6KFdINVNCIoN3OP74fb1oCAlu00PhUnSyO8R2Ek-cgiBCyaYe6XzhZmmHXYn3IM500D2Sd-r0wwY3Wubh1sN5978Z4qtWCq_M1HVlUjQ4KqwNPXXOdSwyP2V-N3_SjtToKngdhWVdHgdQGYKJT3d?purpose=fullsize
 
https://images.openai.com/static-rsc-4/tAYpa3J3tyLQlPzvu1cYsz9YY9wTRMOZq6CNPb6dazIeRSpk_kqjybwwGmzAt_1H5di-7HSlxi2y5-Xh_wnbVe0G1RfrTZ5rEgDMSD_fZxcUbkY4qBpFFCzw0Iluim2p1yIjhRuT8dDwMTHNDjKbmXj2VO33MqSFcf1Fws7ii2U532t8Jm7FE6YBorVQ4lR9?purpose=fullsize
 
https://images.openai.com/static-rsc-4/ENSEuXvWR8qv4ok5Jn-i2Dt0g2JMV3YtIgsfoLL5E_7TxQ-_atlAwTfN06szuTn0IGYSs6yNArIXQEpURI8edTXtBj3qmgBKU-oDuC_zGG9RqS7hZ_e8YePtpjICdWzYzwdAxd6HIYRdpwuYoqUHm4TOWHtn5JZ4sU9JaYHWTDGbIPzJHwTVkoConh_-ZxMi?purpose=fullsize
 
5

What Are Alkanes?

Alkanes are a family of organic compounds made entirely from carbon and hydrogen.

A compound containing only carbon and hydrogen is called a hydrocarbon.

Alkanes contain only single covalent bonds between their carbon atoms.

Because they contain only single carbon-carbon bonds, alkanes are described as saturated hydrocarbons.

The simplest alkane is methane, CH₄.

Other common alkanes include:

  • ethane
  • propane
  • butane
  • pentane
  • hexane

Alkanes are important because they form a major part of fuels such as natural gas, gasoline, diesel, and liquefied petroleum gas.


Hydrocarbons

A hydrocarbon is a compound containing only:

carbon (C)

and:

hydrogen (H)

https://images.openai.com/static-rsc-4/9JmeIeQeNGKsGwq-b35aDG1UlLU5sNBZp33In4fjoXUzbxWP4WjkZtzsx3XK25psTg7Xp2ENpllYPytHWeYuTcqRAdFXDcyE_Nuor3HnMDou00FB9fHDx__16GRgA6gr4dmZ3FyXc5IRQ3PSzNe0WOVNhRK6AxvrGn6GZIvIilwbWj2kPGXugg8CnUupGcAk?purpose=fullsize
 
https://images.openai.com/static-rsc-4/cld_yx-NM_E87zhe1-EUUn-qug_gAXz-0LOH3OSm3wkIO6aJpkZFTl28A7hFa9_32_q4JjfO7r4DEDdKml899Ak12EQbvNIpMfuPPS-E-GzS-6z5FYiyG9JSpFaoFVdPTrlmn_TjiEus03dwBWXQ204Tk6y3XGLNwAl1ZH-W6D3MHfFvhbSb93FlJWa1Mz6t?purpose=fullsize
 
https://images.openai.com/static-rsc-4/vWocCsmvMs8QEFK4EkPSGbAng2g7yAfUAnsjSGakJuVdHk6AgyCxrm2SrmCV3aReOuSDm6i1QL_8zuv-QmfV8KjsCk60Fz146banRv7igI-1vaFXqP8Wbzfmqq5ECqIte18Nzw0ufo9whdy-LfxibVuiz2BRkL-vBKCrtndq8mhFlUgyw6DKx9CiBxIft7y-?purpose=fullsize
 
5

For example:

CH₄

contains only carbon and hydrogen, so it is a hydrocarbon.

C₂H₆

also contains only carbon and hydrogen.

However:

C₂H₅OH

contains oxygen as well as carbon and hydrogen, so it is not a hydrocarbon.


What Does Saturated Mean?

Alkanes are described as saturated.

A saturated hydrocarbon contains only single covalent bonds between carbon atoms.

For example, ethane has the structure:

CH₃–CH₃

The two carbon atoms are connected by a single bond.

There are no:

C=C double bonds

or:

C≡C triple bonds

https://images.openai.com/static-rsc-4/Vwoptw8_zFwjMjTAmOeeOTFeKG6Q5k4yA_6K7eofwalgFhww5ITis0xgNuuscvCF3_eqDsJmLX9CvqxROOpvuLQMuLf9lrlifJ1WZ-R-wnG4eO_U1Nr11y6gQhT_W0EzL4BlLT34na6XYxawOUXPlY7l3Ws_6zDTrg8UZIRo0OfcOqtAULPullSh-DcojUEq?purpose=fullsize
 
https://images.openai.com/static-rsc-4/iImP5Yldh0YAOsjMCeCppm9_1x-gkyr-npX7_nGLV6JH4jBINRw-WXpIeOjAfWctfFo_RmmZUeMpi6mnpHkGoepzpOtmmzwdef2R9Onp_RJyk3fSqpL1QXTUJ_Pez0tCTNYU8xuDGKbv77chnvo5NQJV25Iu8X-wpVHH4jgOa_Ow6PSxtLTsACjlNmGVdR66?purpose=fullsize
 
https://images.openai.com/static-rsc-4/GCXnFq5CKXkK2ZAmBFxShl_CjP9JuW3WmwWSVI2A9cWtmhSGsLmDEz16NgQAedfb2ejO6Sd130ilquv6Lr-A1SKfdQFc_4P01WsjCoT-EUnO2j1ORx45_WAd7aF6QEib6_SmGByQOJJp7a_FMnXBk0QB_wdLjwC2iK2qKYRc_SR6Q3j8CSG7V-96DbkV8wqA?purpose=fullsize
 
5

This is the key feature of an alkane.


Why Are They Called Saturated?

Carbon normally forms:

4 covalent bonds

In an alkane, each carbon atom forms as many bonds with hydrogen atoms as possible while maintaining only single bonds between carbon atoms.

For example, methane is:

CH₄

One carbon atom forms four single bonds with four hydrogen atoms.

Ethane is:

C₂H₆

Each carbon forms one bond with the other carbon and three bonds with hydrogen.

The molecule is therefore "saturated" with hydrogen for that carbon skeleton.


Carbon Forms Four Bonds

Carbon has four electrons available for bonding in its outer shell and normally forms four covalent bonds in stable organic molecules.

Consider methane:

CH₄

The carbon forms:

4 C–H bonds

In ethane:

CH₃–CH₃

each carbon forms:

  • 1 C–C bond
  • 3 C–H bonds

Total for each carbon:

4 bonds

https://images.openai.com/static-rsc-4/Wu8lGMbM8enEYyQDRY_Q-tu1fIRiy-pfX9j2b12rjrKD5cayUKC3N5W2xun63uRFfF91_5WbvVwldv2bngBoKP4WxUMG0G0MzOo_fAqngLq6c31qiFQJ1ycbeXEVapwZbzyrLmzv9X4SP19jBTnQxVLfmi_HopQ3K6-RooLpIWH_o1sWELuoYvAZpkgKASzx?purpose=fullsize
 
https://images.openai.com/static-rsc-4/_n9yIVia-Gsn4BEo4TbooedD1IC22SsyqUldaukZrrKJYMt8xfZ-5uE_0r_2g1Qfj8Xlj94_tj-hUs8jR1sJ1LsbjTS8s8jZwo4ZE6mGttYQjqOR4Rupppf7ay2tu9wkz0ri3PeTw7bsC_DU0xsaw7dyX-hUpNahkMEce0Hl56b6wh2c01tpxvh8zK6EuuvR?purpose=fullsize
 
https://images.openai.com/static-rsc-4/q4c7LIGB9QWQj0cL-CcVUESj18Rzt01wGbK6XYXhl71c55ixoTGxT2M9Gh4LS93ATeRo2kT5ZaKblnkrcvve1xoeDCx-lZ1ayQd-3iMj4hPfsfrmZefBjBk1fS2YouPWR4h4uGr5LV8N4OBNu7tRKfS8RsgGadx5OvgXrXewEijA0UIhSVu9726IvInAxoc3?purpose=fullsize
 
5

Hydrogen Forms One Bond

Hydrogen normally forms:

1 covalent bond

Therefore, each hydrogen atom in an alkane is connected to one carbon atom.

For example, in methane:

CH₄

four hydrogen atoms each form one bond with the central carbon atom.


Covalent Bonding in Alkanes

The bonds within alkane molecules are covalent bonds.

A covalent bond forms when atoms share pairs of electrons.

Alkanes contain:

C–C single covalent bonds

and:

C–H single covalent bonds

https://images.openai.com/static-rsc-4/ZAXcL3TYn_T9xk6nGLczWqrjrM63dm6TJrFHMLHre4tGkZzHkFZH8BlMXuSLL26jYzYY6T3jEUMkybk7lM_d-burRfuPgnzXLeMGRahOO57Z9NRyC1eqZd458lr1hh_3ri7E5suYkO56VHm2EFWbVj2SKkkL2PEiMmMFqSIydWkDDlVQo2MR3JrhSrS2G3Yl?purpose=fullsize
 
https://images.openai.com/static-rsc-4/RU2HXXZ-FCMQWx-JVvnw7Q_lIGGITuGcQf4R1TbioXCZ7ivs71dRErixvN-mbFjblNxEMaV7A4krOZQyhcww5pwp0b-ccQYEYvQC8di9LmODg_kWa8BtOF89rTf1SzxbVoshLrli3_u8esyCqeHNBS3mnYs6FIc58lBVgtwZ9ZTjIE7KyxZItoxmwKQ8I_BE?purpose=fullsize
 
https://images.openai.com/static-rsc-4/QfExQ3y3A-sQiJA6CqPH79Tm0YCH6zn2CH0TxNd8PIkJgBJN9kzY0h2wlFJp5c1F8cBQQ8sX1TYUiaNlGY_LZjpvnlvcb5DfdehbHs7uVXFHp1BwwYbER9MvnEz25MZRV7bX2up2A8pINxX-i9Q4DCUtVZgiNQlV3MSmgNl4aX_keR2haAEIzaHxJk9igqpQ?purpose=fullsize
 
5

There are no ionic bonds within an alkane molecule.


Methane

The simplest alkane is:

methane

Molecular formula:

CH₄

Methane contains:

  • 1 carbon atom
  • 4 hydrogen atoms

The carbon forms four single covalent bonds.

https://images.openai.com/static-rsc-4/7hcvIFjVKiZ5ZPTpqTGeOhyMwXgvIJBS5g9LtunMCE73qMXs2yaOZG1tJATvgDMDJFaZmWrM70mgMWabPSv4USjZlUkgFBZ7mDJB1_4VonyV3xImPI5FqpSpJyghu8gI757oaVpjaWinfZw2efylM1hzBcjSSnWEyJ2Dw-qz7OtvtTscFisHHJxmO7CPu8UJ?purpose=fullsize
 
https://images.openai.com/static-rsc-4/RcFuoH_EK1_gU2w5z30WCuw5p5kQq21-yzVyBfowWOVRMgp71yCr_PR7wfwLDLJdz8zJMXIGPNxc8vT504qMGJq0cdx5X4Sj27fbn4t-ik1PmXb15KJI9rlX97CsTafyxcdXZZ1qAoeJ7HMGgIhHd_ZqH90jUTvjdaiZPRoQIZ8tOJltqt5nziygr2R5MHC8?purpose=fullsize
 
https://images.openai.com/static-rsc-4/bB7WAM-NI4CTi3rp2IpiEp58jd06XQIm1_HZh6bMtvOQXzDflnxSHixFYuuy2sgZl-8cD7zbcES7j-tjmm0qi7H4zJFLXP7W-DeXHv2RIzxgUFHEhou9cTsTbcL06zyOSbzCxSS3V-mD00t1-YvStsyJQnyxmS4IxGOm2MeZKnxRnGjTjiVDyh2mjDxsiGNE?purpose=fullsize
 
5

Methane is the main component of natural gas and is commonly used as a fuel.


The Shape of Methane

Methane is sometimes drawn as a flat structure on paper.

However, the actual molecule is three-dimensional.

The four C–H bonds point toward the corners of a tetrahedral arrangement.

The bond angle is approximately:

109.5°

This arrangement keeps the bonding electron pairs as far apart as possible.


Ethane

The second member of the alkane family is:

ethane

Molecular formula:

C₂H₆

Structural formula:

CH₃–CH₃

https://images.openai.com/static-rsc-4/neJ4_ELz3sf7VoZjB8KzfO1RKDOqET3OTa4cPDL9OR4Qufmiv56Sg7UNLsrk7sJmFaSRH3mm38ALpCeYtJc28Qd32ROrB2dfPy1LSxyOFalm708kGZpr1_OZ6DRu_2AW17DA1KMjf1GRV6m3GDfdBD5pzJ2GySXVIvMCY_U-vk6fpqkN7FXovyODkqkd6-5v?purpose=fullsize
 
https://images.openai.com/static-rsc-4/Wr_ckM8vBeCksE1MbxqQxArnr0T4LA-9poh7C7K49dlr1HKIvVty0lKljZ037xnbUAFVj2e4cHRpN0o4WoylPP22azvRC6tAh2m163OSxK40zbvYmgSrW6M8UcA0lFpaioj0g8Sy6BoyiUmOWYyHyOax8AzYYicALz-e9yigfoZ0JhaFeZQJBOD2vEcV1kAk?purpose=fullsize
 
https://images.openai.com/static-rsc-4/cD7FL0wOvk0Cv1GGt47A-N0iAB_PbAj3Y21t11cwgKBUtxdVyCX0nSnGm7sx_kC6zTWtFKScBAkxD38QfpnZPvNXOR8tjc4Pw0KQ0mdu1kWj-OlXX96jCmkFBQE5DfrZxsgUplwAeayOoQqmnZKCUguvahA2fYiPkx32N8fshwJ2an8-66HHe0TfiXtQpKoZ?purpose=fullsize
 
5

Ethane contains:

  • 2 carbon atoms
  • 6 hydrogen atoms
  • 1 C–C single bond
  • 6 C–H single bonds

Both carbon atoms form four covalent bonds.


Propane

The third alkane is:

propane

Molecular formula:

C₃H₈

Structural formula:

CH₃–CH₂–CH₃

Propane contains:

  • 3 carbon atoms
  • 8 hydrogen atoms

It is commonly stored as a fuel under pressure.

https://images.openai.com/static-rsc-4/774aHLHIpjRoP5brPyCZL3j0lTcmIXU3yviuTP3mg3dwwe2LMCZQWCDQrt2I4xtxq_xCowVoRHxbUT8hbv-cgn-ZIKfDuqpiCZT7yFlR8yBhlOubX7S6KJV5_S57Gvd5LlvmrcmO69TQREZMPfoQoEvgWip9VmQakoghuB_GS7GEvzhWGvQe_kcRTvCO6hN-?purpose=fullsize
 
https://images.openai.com/static-rsc-4/ob80fFjvHtM_8rY35QnuZAAH-xUJXprX69iYlYO1zQGBbp9V9532wHUJz2pi8Jc6OTnQKE7P7s4Q0CKzmpsZiX-O1Z966JE4Khhisa0DSGV4Lzl-LGvTIjRVH9aAWnPFK_pI_XzVk8H4XJM_3tywCG5h9CMPMHNnOyuiQniorthE_FyfXxZqkLHkf9n8NRwS?purpose=fullsize
 
https://images.openai.com/static-rsc-4/0fwKApF8WiF6t621obna4iqft18Zn5dlxuAlzOZcgagvJdx1bxc8bVw45ufrt19WWFMWg47nelia4z306U4gk-h8oOok4Kb47MfwbIyQNuCkztergjxmv-uVgULYO5juDaZmp4KbktBstFT1qJ7U6AZg437a_A_EaNaKrjoG8gzT6MYrDvs_Xl04UcLI6Xyt?purpose=fullsize
 
6

Butane

The fourth member is:

butane

Molecular formula:

C₄H₁₀

One possible structural formula is:

CH₃–CH₂–CH₂–CH₃

Butane is commonly used as a fuel in products such as portable gas canisters.


The First Members of the Alkane Family

Alkane Number of C atoms Molecular Formula
Methane 1 CH₄
Ethane 2 C₂H₆
Propane 3 C₃H₈
Butane 4 C₄H₁₀
Pentane 5 C₅H₁₂
Hexane 6 C₆H₁₄
Heptane 7 C₇H₁₆
Octane 8 C₈H₁₈
Nonane 9 C₉H₂₀
Decane 10 C₁₀H₂₂
https://images.openai.com/static-rsc-4/sWebX0GhlkYWAxIgTaHd3kIwemYSj-CNG0i3Na1k1ZmKbuRk78jyypdvzXGsjE18byMEQND1ioZUbKLGsNtxmswb5rklmOYgTRJ4lfrTuyyMyPSKJzqIPzyvxGhFc_fo_vuZ8V0WB5jj7MIBqYpk_SRjmO7XpKz6aaqFKucEhbzUwu9nhp_dZLopdh_zKb8-?purpose=fullsize
 
https://images.openai.com/static-rsc-4/tTh1pRy7vye1NcWtFjZB51Fm7fc-aUWxR8J8LzDGGLtV8cRR-T-KNt4oTiKG9I65GH0u0nSp8nXnERquHLYJeaNdubM3so_YNYzzG31rzVGCVQW4-LyteNpSvBwbOVrq9qw2H5_Yo_YoeuCeW02ob8p45sCP0caEcdQYgwOjq-JwtehhL11PaVKalJvuD3b1?purpose=fullsize
 
https://images.openai.com/static-rsc-4/DX4M5XopiRTRhgoQMQteRK0sQJ9Sm1M_iOCDmN5kHvjeVfV3hhMk4ryfQeF_Dg0fyE2hUdQ7OhPm3WghppYYBObUBwJYSMUJVp2ahqZAmP7FzcA88QNkZApy4scY6EqMheeG2X0IuTP9HQtdns1oxAVKM31jx5HOf_tvyK4FkpBiv9GTtFZv9oXwe45EsXKK?purpose=fullsize
 
4

Notice that each new member adds:

CH₂

to the previous member.


A Homologous Series

Alkanes form a homologous series.

A homologous series is a family of organic compounds that have:

  • the same general formula
  • similar chemical properties
  • the same type of functional pattern
  • a gradual change in physical properties
  • successive members differing by CH₂

For example:

Ethane:

C₂H₆

Propane:

C₃H₈

Difference:

CH₂


Naming Alkanes

The beginning of an alkane's name tells us how many carbon atoms are present.

meth- = 1 carbon

eth- = 2 carbons

prop- = 3 carbons

but- = 4 carbons

pent- = 5 carbons

hex- = 6 carbons

hept- = 7 carbons

oct- = 8 carbons

non- = 9 carbons

dec- = 10 carbons

The ending:

-ane

indicates that the compound is an alkane.

https://images.openai.com/static-rsc-4/VOepzeC-QC180PwgB4P9lXkmhnWvBd4QLvvAhBjs3DV1O_XR72kbMqG_0p9M8I2RWtzjJQQinT3kLWSGzDrl-aF40fYUiAi2x_pcN5Wrz8gaVpygRGWEY58io0NocD0qRoDnnhpbDUcPGs29Dx6XeXpPqrR_du4HLGa9lswhR4CjI1H3sejywMdg8d1et9mW?purpose=fullsize
 
https://images.openai.com/static-rsc-4/VLVdwUGph1FOCzPtBK4ymkXn7Q3rmm1x7eWyVOScCNwCnISseMcAJ22STA1YKO94aYCUiLiN_ke9wrmoCxXJr_dy7maLkzn_U-cVYCXsCko1vsFOFIAsBthkoyjekryZkot_BrW4zcjKAwWCOJLpC-u1_CsvX8XGp3xoFqOmpzHA8D_78WB4kFcyyOZ5bAi0?purpose=fullsize
 
https://images.openai.com/static-rsc-4/zIPDl3f4McPfFp3_SqQtw_z-PhjusbNgel29sbSucOqBPe1jnakMk8umaBd52U9UIATU7lzjySSu6wfg_i8guhIB6EUwcvJH-wyNWoY82hS1qSsMghwDFaXxtxzbogabsXngapwhp5dm7Zr-llLrgXFUE3zggUo-YqDv-PD_8bWRm5V8I98qrhkljFsvMlL8?purpose=fullsize
 
4

The General Formula of Alkanes

All simple acyclic alkanes follow the general formula:

CₙH₂ₙ₊₂

where:

n = number of carbon atoms

This formula allows us to predict the molecular formula of an alkane.


Using the General Formula

Suppose an alkane contains:

5 carbon atoms

Then:

n = 5

General formula:

CₙH₂ₙ₊₂

Number of hydrogen atoms:

2(5) + 2

= 12

Therefore:

C₅H₁₂

This is pentane.


Another General Formula Example

Suppose:

n = 8

Hydrogen atoms:

2(8) + 2

= 18

Formula:

C₈H₁₈

This is:

octane

https://images.openai.com/static-rsc-4/tkCMZElWw2DvTCAKYq52adzs6f0gDJGknnFjYtV76ptZV_fGUvn_C07b_ryOAtDdKCdHCrJ5smqhXg8wkyWVavKmGIT4XtF59_0LrCzMQcy3RqDKh_JSEcuOBc7Xy4zejP5Yr1YAeDpLDj10a5gm1_JzAnmDZUjaE7ne_Y09UqENkfKavrBv9XRqzQUMDLcK?purpose=fullsize
 
https://images.openai.com/static-rsc-4/DX4M5XopiRTRhgoQMQteRK0sQJ9Sm1M_iOCDmN5kHvjeVfV3hhMk4ryfQeF_Dg0fyE2hUdQ7OhPm3WghppYYBObUBwJYSMUJVp2ahqZAmP7FzcA88QNkZApy4scY6EqMheeG2X0IuTP9HQtdns1oxAVKM31jx5HOf_tvyK4FkpBiv9GTtFZv9oXwe45EsXKK?purpose=fullsize
 
https://images.openai.com/static-rsc-4/8Q4Kvd5fkhHD-zQHcskz6h_iJOVj0SFuFTmpErWi7uOadcI9HTGvwnMItiC7VhV-sYp5yMBw5_LciVhRcgS6olX7q9vLsDANK-tngRtV_srM8LJCyhdPjT5SDPH00z7-p8aYYu_W1ZbSZlAFJBt6QncSkkZ0ykxitea0bg6sTgYbY99ozvtWMJJqVF5dcjsE?purpose=fullsize
 
6

Why Is the Formula CₙH₂ₙ₊₂?

Consider a straight chain containing several carbon atoms.

Each carbon needs:

4 bonds

The carbon atoms inside the chain are bonded to two other carbon atoms.

The carbon atoms at the ends are bonded to only one other carbon atom.

The remaining bonds are filled by hydrogen.

This produces the relationship:

number of H atoms = 2n + 2

Therefore:

CₙH₂ₙ₊₂


Identifying an Alkane from Its Formula

To determine whether a molecular formula could represent an acyclic alkane:

Step 1: Identify the number of carbon atoms.

Step 2: Substitute that number into:

H = 2n + 2

Step 3: Compare the predicted number of hydrogens with the formula.


Example: Is C₆H₁₄ an Alkane?

Number of carbon atoms:

n = 6

Calculate:

2(6) + 2 = 14

The formula contains:

14 hydrogen atoms

Therefore:

C₆H₁₄ fits the general formula for an alkane.


Example: Is C₅H₁₀ an Alkane?

Number of carbon atoms:

n = 5

An acyclic alkane would require:

2(5) + 2 = 12

So its formula would be:

C₅H₁₂

But the given formula is:

C₅H₁₀

Therefore, C₅H₁₀ does not fit the general formula for an acyclic alkane.

https://images.openai.com/static-rsc-4/t5z7kBjefn47Meb8k3A9IgZTVGcONYVvIKGLT7ED1JWaiR-NJzEiI_rn528okccobBgw1AxzW2aNkGym1VWqUQQ881dUbzal5yZgZbvzBTWOaKdDjcBXns4vs-IBJS1Zah5t4p8vxU8vSLhrj_6QD09uhWXXdhwT8okezTcWqgS2aPbGgNPIErQvyi3_iC82?purpose=fullsize
 
https://images.openai.com/static-rsc-4/vs7QlWzQO53WqIWNOyJJaTlCtpV9BaZO6XJmTv12mmho8hoOT8F-4SaYJWrNEwe1bAWkJ_UD_x7S-H2cixv9VGGb_j3n6SqJK60f88_IypyM0P_PmWsifD0qofhXuRC5JLGD2tehLyUZ870zjwISfGLFgNzWUvvTdN0LvaToBnQrdTdD27pSMj_WCHEXS8v_?purpose=fullsize
 
https://images.openai.com/static-rsc-4/iImP5Yldh0YAOsjMCeCppm9_1x-gkyr-npX7_nGLV6JH4jBINRw-WXpIeOjAfWctfFo_RmmZUeMpi6mnpHkGoepzpOtmmzwdef2R9Onp_RJyk3fSqpL1QXTUJ_Pez0tCTNYU8xuDGKbv77chnvo5NQJV25Iu8X-wpVHH4jgOa_Ow6PSxtLTsACjlNmGVdR66?purpose=fullsize
 
5

A molecular formula that does not fit the alkane formula may belong to another type of compound.


Important Limitation of the General Formula

The formula:

CₙH₂ₙ₊₂

applies to acyclic alkanes, meaning saturated hydrocarbons without carbon rings.

Saturated hydrocarbons containing rings are called cycloalkanes.

For example, cyclohexane has the formula:

C₆H₁₂

but it still contains only single carbon-carbon bonds.

So when using molecular formulas to identify alkanes, it is important to know whether the question is referring specifically to the ordinary acyclic alkane homologous series.


Molecular Formula and Structural Formula

A molecular formula tells us the number of each type of atom.

Example:

C₄H₁₀

A structural formula gives additional information about how atoms are connected.

For example:

CH₃–CH₂–CH₂–CH₃

https://images.openai.com/static-rsc-4/2qsn6yBSAlwAMu4jCNcdiAaA_Mi55vSa00t6ovpE0Uv4tNZC4l-XnwF4iQj_QRJtL8WNvQ0YiBbxRLd42wQj0Ti5LyxRt1LS7Buu4X7quuMnxGPyv0IalhH4QP8oxbzhvwZg1DktgA3ErafHeed7Ido8KMLJITK7f09ceCZAYaCdD4PA1Snt_tAkb1YtyAyR?purpose=fullsize
 
https://images.openai.com/static-rsc-4/jVjV4N0bhXNuA0A6MKyHV0R2toUDC8psk0DGp8ejLNQhtm6ZW4555H-3Ye5LaPQNU7iJqgDyKdSz83Zz0f6_UqiaTIOnuSOb9B5QwzZYiMzAqQt1lLgqa0-xlNE6M4-DD7O4pM9jNMrddMBNpEiiB4Wua5E6jRHFG29TABtLbxbK6OyGYOfHo_f7cWoah1uN?purpose=fullsize
 
https://images.openai.com/static-rsc-4/GtQLI040nM5B9Yfd3QDTV8SDAJmVlYYU4-hZlpVHugdb5uZXPJU3Tr7xVIlVGZ2KTFU_pffYXCuuhdDw-ZcCafsbKuUSRE399SWATc4-Sti28CZvm6z5bvouGaSyPhrA1_XTOFyWMdzsWkRsyZr_GuBHJGf1B_M2vv96uLcStnqFwKSf8bp6FdBCTLQ6fRM0?purpose=fullsize
 

Both represent butane, but the structural formula provides more information about bonding.


Displayed Formulas

A displayed formula shows the individual bonds between atoms.

For example, methane can be represented as:

 
    H
    |
H - C - H
    |
    H
 

Each line represents a:

single covalent bond

Displayed formulas are useful because they make it easy to count the bonds formed by each atom.


Counting Bonds in an Alkane

Consider propane:

CH₃–CH₂–CH₃

Carbon 1:

3 C–H bonds + 1 C–C bond = 4 bonds

Carbon 2:

2 C–H bonds + 2 C–C bonds = 4 bonds

Carbon 3:

3 C–H bonds + 1 C–C bond = 4 bonds

Every carbon forms:

4 covalent bonds

Every hydrogen forms:

1 covalent bond


Single Bonds and Saturation

Compare these carbon-carbon bonds:

C–C

single bond

C=C

double bond

C≡C

triple bond

Alkanes contain only:

C–C

single bonds.

https://images.openai.com/static-rsc-4/9JmUEdoC2X23v6ZxDN917z9V4AdflSIenwp8J-BEJCWPG9qhLYFioa5QSen3eCcTWZCI5UPH_f2Pub8znEwZsDpdLd-OoBnZAIRSDZO9TxBeu4cNYKG1PAok083JQz_2LJJ6fU4lQwQh9u3_G0s-8JtBF76p8FCHiiaaoPnw8RL-wFs7NekPb3o6cnMjk_iF?purpose=fullsize
 
https://images.openai.com/static-rsc-4/3zseP0uVEXZ7hrsDEHKgjCyELniiVpEtBHQHFA3cC_tHR0h70ptA77qP_Cr68zXQaMLQpX9JMo249GIOze8EWCEWwspfhEOno2hhqzAKzTFwHTtvoUlPrHKV05S0yHEsaOnnSanRnkbIZUoSCphHQCdHh0eGESQQsA9-iuJUR6DZTUKmRwmqK8kobyO9JSCG?purpose=fullsize
 
https://images.openai.com/static-rsc-4/I4OBfC6ZRGOEMLHSjUHZgZIh8a7c667Ru3Rv3AyjI0e-vdzPbmD5lMFRYu4nwfy72V2nX3A_dcvOu72Vgt8PnopJm7pwzGRFJq0sLLsVauv1zR-RV8o4tk9r7gFzvmm5l5xkcRiCYkaYJOCSx6EqFRX18pkuaY4GtXrQfkRUtPaevv5UyZWEi-n21G74yDrZ?purpose=fullsize
 
4

Compounds containing carbon-carbon double or triple bonds are described as unsaturated.


Alkanes Compared with Alkenes

Alkanes:

  • saturated
  • only C–C single bonds
  • general formula CₙH₂ₙ₊₂ for acyclic alkanes

Alkenes:

  • unsaturated
  • contain at least one C=C double bond
  • simple acyclic alkenes containing one double bond have the general formula CₙH₂ₙ

For example:

Ethane:

C₂H₆

Ethene:

C₂H₄

The alkene contains fewer hydrogen atoms because of the carbon-carbon double bond.


Why Alkanes Are Molecular Substances

Alkanes exist as individual molecules.

Strong covalent bonds hold the atoms within each molecule together.

However, the forces between separate alkane molecules are much weaker than the covalent bonds within the molecules.

This distinction helps explain many physical properties of hydrocarbons.


Structure of Larger Alkanes

As more carbon atoms are added, the carbon chain becomes longer.

For example:

Pentane:

CH₃–CH₂–CH₂–CH₂–CH₃

Hexane:

CH₃–CH₂–CH₂–CH₂–CH₂–CH₃

https://images.openai.com/static-rsc-4/sWebX0GhlkYWAxIgTaHd3kIwemYSj-CNG0i3Na1k1ZmKbuRk78jyypdvzXGsjE18byMEQND1ioZUbKLGsNtxmswb5rklmOYgTRJ4lfrTuyyMyPSKJzqIPzyvxGhFc_fo_vuZ8V0WB5jj7MIBqYpk_SRjmO7XpKz6aaqFKucEhbzUwu9nhp_dZLopdh_zKb8-?purpose=fullsize
 
https://images.openai.com/static-rsc-4/7Se--TjSDYU0qJiOKhSwHnU0fClnIqGOIvDmCLZHBmRgO5Rzd-3gAYN-N-a8YYDzG0Z_TeFUSiH0iZXBjsLnm_VVhQOwjNQ0NeCDJf1-rtTj7ec3bDogb-MLZUK9cW-8JSoK4Ihf7A92ohYDAr0afAVibTlVggNYcArKAkvcBp-s0MPxXlUkPBesJM104wJP?purpose=fullsize
 
https://images.openai.com/static-rsc-4/NZetfMdPmRnATzbQ4wkZxQC6gdDpu2jxqHYz-JMy_e8ug_xKOk89eYsI8mRpEVq_fqx-wloB2QnMGDi5xSNNgDgJYhgBZyxOiolbA4GYowgy3pkQ8qQ8r3bV7knYM4LnPqrioAfOm6LIWGKzHlzl3qKcHRpccqc9ZaRfDzvK3G5l5DuuswfTVvqKGN4uNhgA?purpose=fullsize
 
5

Each additional carbon in the homologous series effectively adds:

CH₂

to the molecular formula.


Straight-Chain and Branched Alkanes

Alkanes do not always form straight carbon chains.

For example, the molecular formula:

C₄H₁₀

can represent different arrangements of atoms.

One arrangement is straight-chain butane.

Another is a branched structure called 2-methylpropane.

https://images.openai.com/static-rsc-4/s6xkV_ZuErr_i5x-L0svWltEZrDTRf7C0GL6m_vi-m9livBQAjUFJI148fc-iicbhz3j605d_4jYfpPUTungpSMurWKOQMS9gbVlodhiSbD0KyH2pUn8t8OC3rLs5f4MUJVFrI88Z3QX9H_u0CQVBXyDs18CoyBaW9ufiaJqNEt00tPKf9xpdPqyk3jViAxC?purpose=fullsize
 
https://images.openai.com/static-rsc-4/w-KJXRoEZWzfuUQNh_ZSbijbspkG8T1HGKuUVgsRJQY40ZbkosrVcRrGU7OZ-PhrCB2I7aVRbeiV2uZEgPotTu1JkTm2F6v28-VmS39Nd0bvB1w1mh2TVcvySEKtMFUubGoFjeYN4Rdz8-t8AsOupr8f7Gynd7u0S72mE_PQBw-RGOl-bPoQ5MPtqPUIcc7U?purpose=fullsize
 
https://images.openai.com/static-rsc-4/8nyosEzeC2ZvEaAXlM8t27Kiic1OoFZMqD5BI22iy_xnFzuW5Aw4-lAh2-nP-lomqFO_ba5MpnFKZUjDGfZVuMYdGAVvgWe92f4z1xW4LlCScT65gGIsE4u0tsDFiArsGNu6Hsk_TLeA2Rg0_7i6vTtxk0myMSF-UKQJpRGMCaMgYHVRo7uEjAuOnMPj10PM?purpose=fullsize
 
4

These compounds have the same molecular formula but different structural arrangements.

They are examples of structural isomers.

Both are still alkanes because they contain only single carbon-carbon bonds.


Physical Trends in the Alkane Family

As the carbon chain becomes longer, several physical properties change gradually.

Generally, larger alkanes have:

  • higher boiling points
  • higher melting points overall, although the pattern is not perfectly smooth
  • greater viscosity
  • lower volatility

Small alkanes are often gases at room conditions.

Medium-sized alkanes are commonly liquids.

Very large hydrocarbons may be thick liquids or solids.

https://images.openai.com/static-rsc-4/4fT0EDaQI7bdJuUN_3czjb0LH7-M6fro1y0nXGNVSb8eiD78TTWl8nYf0eOk7Z3cdWqhS6eucKDKS9XW_-AEU05M6LDmmd_xbjaVwxr7cAN7M_rtg71yncNMJJYpbade5R_HCOdexa0DLfOTbcrjOgjiw6p1b3HwY0bBHN52LlhqRYqp4pnW3ProcxIamWkA?purpose=fullsize
 
https://images.openai.com/static-rsc-4/2JuJI9t8atNho8jUh6JOFVA2FoXkMywiPHfqfAz914kD_1SSC15M3MujXj4Vxi8NFnV4RKN955kLkudrHeYzrjOTrMoyKFoEEcM57c5u8nHJeeuahJu7xsNKsh3D4vAIqZNnlkoIoJFetNW9KXS_ofEcKHaXxSy5iInM_OMmAWtUFRIjBnFrsToouC5KchJ6?purpose=fullsize
 
https://images.openai.com/static-rsc-4/52q0X_sTmurQO5R1S_NZXQeO0dOjOzm-afnQyMyVk4gcWNeCeqK-Y7mtt__0gjDDPKOLm_RBHlLPixmqBNiaCy5H-J2_75zgBqNNorZo14h9C22WhAc0pHkAHm9qHrTbvwuz91LN72cHaI9bO2VjPDqjtfkpVXjnRAvm9xZ5_zjkE_44XSe96QirzHxxFrZg?purpose=fullsize
 
6

This gradual change in physical properties is characteristic of a homologous series.


Alkanes as Fuels

Many alkanes are useful fuels because they release energy when they undergo combustion.

Examples include:

  • methane in natural gas
  • propane in fuel cylinders
  • butane in portable fuel canisters
  • hydrocarbons in gasoline
  • hydrocarbons in kerosene and diesel
https://images.openai.com/static-rsc-4/kYRZ0W2wuQrahifkVAQvebUILg0nWhP_yZ1zaAl4W22iBl51XoMax6eweYhPuG0ToDmwrdtJ60Z_uyEJuKKfWqh2-8HD2nFx95pJt2x0znL_SRnmmCGtPC3fYf3Jad9JVZz5Uvb_jV-BNG7aRrKP7L9CkEeP1rdtu35AwxzgNAw85NnHCRVBeITIPvRFTDtj?purpose=fullsize
 
https://images.openai.com/static-rsc-4/tGr2zkyvTOqttIi5TsjyCjjNynh2AiV8H0rI1pjcYMuLqgFZkmEjXFHdyUiNy62zUOTFzOOLDCF6iibvpxMiHarKrrdYg3Qy8jg8kag0mt0y9V5wJJV6qzmA0T9BxIoVzR75K32_cPWYJJLtUGxz7IVL8VmNAOtE-QwSRzWhZs-ichMyaUsgFnSRPrtB7frr?purpose=fullsize
 
https://images.openai.com/static-rsc-4/K7QFjPpIVHsysOeCvKe36IFwNtDxvxXLfgBJ4F66ckd_gZaRJK88U1g8is4JpUu-0y9_KHxkGZuHX10sNUfhtn8tY_Lw-1iiJlXdy4vKt6Q7Yl4v7wMNA_DFfxKEbEN34aOY2GxcG5GvzyJcC9ZcyfqI5w2DCM_CRDyo0YcH3Oi3hbdJ38R3HCyMcBaT44Nj?purpose=fullsize
 
5

The properties of different hydrocarbons make them suitable for different applications.


Complete Combustion

When an alkane burns in sufficient oxygen, complete combustion produces:

carbon dioxide + water

For example, methane:

CH₄ + 2O₂ → CO₂ + 2H₂O

Energy is released during the reaction.

This is why methane can be used as a fuel.


Carbon Chains in Everyday Fuels

Different fuels contain hydrocarbons with different ranges of carbon-chain lengths.

Shorter hydrocarbons tend to be more volatile.

Longer hydrocarbons tend to have higher boiling points and greater viscosity.

This helps explain why hydrocarbon mixtures can be separated and used for different purposes.


Worked Example 1: Identify the Alkane

Is:

C₄H₁₀

an alkane?

Use:

CₙH₂ₙ₊₂

For:

n = 4

Hydrogen:

2(4) + 2 = 10

Therefore:

C₄H₁₀ fits the general formula.

It is an alkane.


Worked Example 2: Predict a Formula

Find the molecular formula of an alkane containing:

7 carbon atoms

Use:

CₙH₂ₙ₊₂

n = 7

Hydrogen:

2(7) + 2 = 16

Formula:

C₇H₁₆

This is heptane.


Worked Example 3: Identify a Non-Alkane Formula

Does:

C₃H₆

fit the acyclic alkane general formula?

For:

n = 3

Expected hydrogen:

2(3) + 2 = 8

Expected alkane:

C₃H₈

Therefore:

C₃H₆ does not fit the acyclic alkane general formula.


Worked Example 4: Find the Number of Carbons

An alkane has the formula:

C₉H₂₀

Number of carbon atoms:

9

Check:

2(9) + 2 = 20

Therefore, the formula follows:

CₙH₂ₙ₊₂

The alkane is:

nonane


Worked Example 5: Find the Number of Hydrogens

An alkane contains:

12 carbon atoms

Use:

H = 2n + 2

H = 2(12) + 2

H = 26

Formula:

C₁₂H₂₆


Worked Example 6: Comparing Two Hydrocarbons

Consider:

C₅H₁₂

and:

C₅H₁₀

For five carbon atoms, the acyclic alkane formula predicts:

H = 2(5) + 2 = 12

Therefore:

C₅H₁₂

fits the alkane formula.

C₅H₁₀

does not fit the acyclic alkane formula.


Worked Example 7: Bonding

Consider:

CH₃–CH₂–CH₃

This molecule contains:

  • 3 carbon atoms
  • 8 hydrogen atoms
  • only single covalent bonds

Its molecular formula is:

C₃H₈

Therefore, it is:

propane

and belongs to the alkane family.


Worked Example 8: Following the Pattern

Complete the sequence:

CH₄

C₂H₆

C₃H₈

C₄H₁₀

Next member:

Add:

CH₂

Therefore:

C₅H₁₂

The next alkane is:

pentane


Recognizing Alkane Formulas Quickly

A useful pattern is:

Carbon atoms:

1, 2, 3, 4, 5, 6...

Hydrogen atoms:

4, 6, 8, 10, 12, 14...

Each time carbon increases by 1:

hydrogen increases by 2

This follows directly from:

CₙH₂ₙ₊₂

https://images.openai.com/static-rsc-4/XApst9y22PcxKL7AeBPEUeqWUCm0W8DjG_H_jhrp2HcKGBp9NtFcFFruP7LTka-0WuznNTQjJbF30CsKXAzUzVfmOyEuOziYnpoUlqaTsE86jeJg3TOshw6An55nUGX9Ptecrfme2YyykrDsZyu8ssc6rMgRxVXsCogdtQl8hGsl2eshP7JS0LFGp0UFcIY9?purpose=fullsize
 
https://images.openai.com/static-rsc-4/h_qixeC-9CK7jWm2t_WIlneF-2MzKVRlNicSx-iHfObC51El7kzfEiYxx2smzDlWO6E4kQQIwir9I2nlEg0J0NUFht3mSrjxXYMDsGQVquR82Eu-2I0SI3rgjdRZdI-ku51834oEu2iWXnTRU-BXT--s_8p9qzNtjQ8uoVBzViu2OY8ggjZYsNeVcKkCzEQj?purpose=fullsize
 
https://images.openai.com/static-rsc-4/ozYJ0oH1suUwp19i5-ems09Vhq-BgBPcd7HEzRkD-QHTcelqVw2en0KA5wJzNoXUr2zYi8JzL_wda-8ZYHfRQ42H1KwadOEFpWQFyBFy40A1WsD9PvXlXPKrkb8EeNepykNVaINI7atjyglS_0sFr1u7u2ht8BMmiuh1SxMhWEO9AJgjgyc--t18xjHzBPq4?purpose=fullsize
 

A Reliable Alkane Identification Strategy

Step 1: Check the elements.

Does the formula contain only carbon and hydrogen?

If not, it is not a hydrocarbon and therefore cannot be an alkane.

Step 2: Count the carbon atoms.

This gives:

n

Step 3: Calculate:

2n + 2

Step 4: Compare with the number of hydrogen atoms.

Step 5: If the formula matches CₙH₂ₙ₊₂, it can represent an acyclic alkane.

Step 6: If a structure is provided, check that all carbon-carbon bonds are single bonds.


Common Mistakes

Mistake 1: Saying every hydrocarbon is an alkane

Not all hydrocarbons are alkanes.

Some hydrocarbons contain double or triple bonds.


Mistake 2: Saying saturated means "full of carbon"

Saturated means the carbon framework contains only single carbon-carbon bonds, allowing the maximum number of hydrogen atoms for that acyclic carbon skeleton.


Mistake 3: Forgetting the +2

The alkane formula is:

CₙH₂ₙ₊₂

not:

CₙH₂ₙ


Mistake 4: Thinking alkanes contain ionic bonds

The atoms within alkane molecules are held together by:

covalent bonds


Mistake 5: Thinking carbon forms only one or two bonds

Carbon normally forms:

4 covalent bonds

in alkanes.


Mistake 6: Thinking hydrogen forms four bonds

Hydrogen normally forms:

1 covalent bond


Mistake 7: Identifying a compound from the number of carbons alone

For example:

C₄H₈

contains four carbon atoms, but it does not match the acyclic alkane formula:

C₄H₁₀


Real-World Connections

Alkanes are some of the most important compounds used as fuels and chemical raw materials.

https://images.openai.com/static-rsc-4/eAzCxxlLrIHuG8j3yrw3FB3oYNZGCREjfrFBaGjybidSSVaoLaET1lPLWocteDItFSkX2oxecenUnltE5DdIgrggYZD_tonA29lJQg-_TRmU8mx5S5P5ciAO0_3bUURy6V2x2RA9uiIUTopM4FnfS31IbdMYUB9Nxy9OoTFgfAbQQ3IA5dGERXxT8KKL4Kmt?purpose=fullsize
 
https://images.openai.com/static-rsc-4/tGr2zkyvTOqttIi5TsjyCjjNynh2AiV8H0rI1pjcYMuLqgFZkmEjXFHdyUiNy62zUOTFzOOLDCF6iibvpxMiHarKrrdYg3Qy8jg8kag0mt0y9V5wJJV6qzmA0T9BxIoVzR75K32_cPWYJJLtUGxz7IVL8VmNAOtE-QwSRzWhZs-ichMyaUsgFnSRPrtB7frr?purpose=fullsize
 
https://images.openai.com/static-rsc-4/XyA0fTGPFrAizcoiaz2nuu3DNJYsPXPcc2ryZkBLfbSdhFsgATXYcklIENE8suWmRCc6k8UhMpNjitu4QDW8rh1AL18uiajMtDK_nH0eRKZZaiLt_qM0fZU5ZqOeHgXC4OotGwgK9fYpnSebwgaZU8f8hO6qE84_h3uVIQl2P7gYwiLTiqboGGX8xRXbDENR?purpose=fullsize
 
5

Examples include:

Methane

Major component of natural gas.

Propane

Used in heating, cooking, and portable fuel systems.

Butane

Used in some portable fuel canisters.

Larger alkanes

Found in petroleum-derived fuels and other hydrocarbon products.

Understanding the structure of alkanes provides a foundation for studying fuels, petroleum chemistry, combustion, and other families of organic compounds.


Did You Know?

Methane contains only five atoms:

1 carbon + 4 hydrogen

but some hydrocarbons contain hundreds or even thousands of carbon atoms.

Organic chemistry contains an enormous variety of compounds partly because carbon atoms can form strong covalent bonds with one another, creating:

  • chains
  • branches
  • rings

This ability of carbon to bond to itself is one reason carbon chemistry is so diverse.


Key Terms

  • Alkane: Saturated hydrocarbon containing only single carbon-carbon bonds.
  • Hydrocarbon: Compound containing only carbon and hydrogen.
  • Saturated: Containing only single carbon-carbon bonds.
  • Covalent bond: Bond formed through the sharing of electron pairs.
  • Single bond: Covalent bond involving one shared pair of electrons.
  • Molecular formula: Shows the number of each type of atom in a molecule.
  • Structural formula: Shows how atoms are connected.
  • Displayed formula: Representation showing individual bonds between atoms.
  • General formula: Formula representing an entire family of related compounds.
  • Homologous series: Family of organic compounds with the same general formula and similar chemical properties.
  • Carbon chain: Sequence of carbon atoms bonded together.
  • Structural isomer: Compound with the same molecular formula as another compound but a different arrangement of atoms.
  • Combustion: Reaction with oxygen that releases energy.
  • Acyclic: Structure that does not contain a ring.

Key Formula

For the ordinary acyclic alkane homologous series:

CₙH₂ₙ₊₂

where:

n = number of carbon atoms

Examples:

n = 1 → CH₄

n = 2 → C₂H₆

n = 3 → C₃H₈

n = 4 → C₄H₁₀

n = 5 → C₅H₁₂

n = 6 → C₆H₁₄


Key Takeaways

  • Alkanes are hydrocarbons, meaning they contain only carbon and hydrogen.
  • Alkanes are saturated hydrocarbons.
  • Saturated hydrocarbons contain only single carbon-carbon bonds.
  • The atoms within alkane molecules are joined by covalent bonds.
  • Carbon normally forms four covalent bonds.
  • Hydrogen normally forms one covalent bond.
  • Alkanes contain C–C and C–H single covalent bonds.
  • The general formula for acyclic alkanes is CₙH₂ₙ₊₂.
  • The first four alkanes are methane, ethane, propane, and butane.
  • Successive members of the alkane homologous series differ by CH₂.
  • Molecular formulas can be checked against CₙH₂ₙ₊₂ to determine whether they fit the acyclic alkane series.
  • Molecular formulas show which atoms are present, while structural and displayed formulas provide information about how the atoms are connected.
  • Alkanes can have straight or branched carbon chains.
  • Different structural arrangements can produce structural isomers.
  • Alkanes are an important foundation for understanding organic chemistry, hydrocarbons, petroleum, and fuels.
 
 
 

2. Naming Alkanes

Learning outcomes
  • I can identify the first members of the alkane homologous series.
  • I can apply IUPAC naming rules to simple alkanes.
  • I can determine the number of carbon atoms from an alkane name.
  • I can write the correct name for a given alkane structure.
  • I can write the correct formula from an alkane name.

https://images.openai.com/static-rsc-4/K1jSE_sfMbCs02HK8Yg6fnA9BqL_OI9WfK9LkANGzacGb-Kb8roY4MgxqMjTo8xFvWaS-TBk2XO18MQJtcuaJIxdg3JCdyYw2T13jC01VEA6KAaYuTftHbcPQu95fIZSvuT9hFuRnz2XjIlXv6r063Pf3s7Js5wUi5Wt7V2uQyADI-NkhwRtyJ_NKZTaiTCN?purpose=fullsize
 
https://images.openai.com/static-rsc-4/XSMZp-GIOu8VqMOEieAPEQjDPylUY2geb1mA7QPS5P5YhmJSDlmHUMv5VeAJ1pIn4g-IZ2qBBh4eRiSw1H7FCVeF-8fGUW_Qw7P06xNVEYJpFQmF8fL3yvwluaakvGHK8lz8J4OTxDWYGPGH1W9IK7pLvQKzX6AKXz8j3qYrPqI_4OD3bl4rXDWK1pVsgJYX?purpose=fullsize
 
https://images.openai.com/static-rsc-4/8ZP3aYR0pTod9dY7NTMvGtwTMcFTd7TvlAu7DraS4wUpgZT3ojisL9m5PkYv0YdjZzkWL7tK4mFWkATAJv_Pm9CBxUkCPBvhskNcmbG4cH_xLCfbz7AfIQHO8G-WwgW09QRzHwXpOJT53lDoRqiH9GCDTwr4fLggGLpjK74CI4a1C4No-wF9X9Pn-IyvTaLS?purpose=fullsize
 
6

Why Do Chemical Compounds Need Names?

Millions of organic compounds are known. Chemists therefore need a systematic way of naming them.

The International Union of Pure and Applied Chemistry (IUPAC) provides internationally accepted rules for naming chemical compounds.

A systematic name gives information about the compound's structure.

For simple alkanes, the name tells us:

  • how many carbon atoms are present
  • which carbon chain is the longest
  • whether branches are attached
  • where those branches are located

Review: What Is an Alkane?

An alkane is a saturated hydrocarbon.

This means it contains:

  • only carbon and hydrogen
  • only single carbon-carbon bonds

For acyclic alkanes, the general formula is:

CₙH₂ₙ₊₂

where n is the number of carbon atoms.

Examples:

CH₄

C₂H₆

C₃H₈

C₄H₁₀

https://images.openai.com/static-rsc-4/91k_-HJN1u4p2zwtRuFXupcLXopTH9ffRP0GDXHLoCfK9jumEAo2gVD-wl9gqoaknfqUp4sygmrDMKAA-EF8INj9HDCFA9lkdrezMPGQUK2JJlFdgtvUAxt89s6r9NrPpLrg2YQjl6ICSZxeQvjFEY8vrFEmm4aig8eFFF1eMfO8wATDzymqjnSXM3_HT_Rt?purpose=fullsize
 
https://images.openai.com/static-rsc-4/Vwlbr12lOevsKcImk-oNj2gQ7N_1TKzaHUdwzt7L4O0-JBFUu5Xn_aDQfo97PbCfJ0anRJayX2pWGfxmkHdjkkY4ZgXwwICJBVZO1Hi1v8kF51kk-a4tKDbOlzCWeE0AqdcwSqs4O6B6-hqh856UaULk9HfrdM_J67fCeAf7UouP575awkGaZt55hEb-_xgG?purpose=fullsize
 
https://images.openai.com/static-rsc-4/tkCMZElWw2DvTCAKYq52adzs6f0gDJGknnFjYtV76ptZV_fGUvn_C07b_ryOAtDdKCdHCrJ5smqhXg8wkyWVavKmGIT4XtF59_0LrCzMQcy3RqDKh_JSEcuOBc7Xy4zejP5Yr1YAeDpLDj10a5gm1_JzAnmDZUjaE7ne_Y09UqENkfKavrBv9XRqzQUMDLcK?purpose=fullsize
 
6

The Alkane Naming Pattern

The names of alkanes have two important parts:

prefix + ane

The prefix tells us the number of carbon atoms.

The ending:

-ane

tells us that the compound is an alkane.

For example:

prop + ane = propane

The prefix prop- indicates three carbon atoms.


The First Ten Alkanes

These names are important to learn.

Number of Carbon Atoms Name Molecular Formula
1 Methane CH₄
2 Ethane C₂H₆
3 Propane C₃H₈
4 Butane C₄H₁₀
5 Pentane C₅H₁₂
6 Hexane C₆H₁₄
7 Heptane C₇H₁₆
8 Octane C₈H₁₈
9 Nonane C₉H₂₀
10 Decane C₁₀H₂₂
https://images.openai.com/static-rsc-4/DX4M5XopiRTRhgoQMQteRK0sQJ9Sm1M_iOCDmN5kHvjeVfV3hhMk4ryfQeF_Dg0fyE2hUdQ7OhPm3WghppYYBObUBwJYSMUJVp2ahqZAmP7FzcA88QNkZApy4scY6EqMheeG2X0IuTP9HQtdns1oxAVKM31jx5HOf_tvyK4FkpBiv9GTtFZv9oXwe45EsXKK?purpose=fullsize
 
https://images.openai.com/static-rsc-4/sWebX0GhlkYWAxIgTaHd3kIwemYSj-CNG0i3Na1k1ZmKbuRk78jyypdvzXGsjE18byMEQND1ioZUbKLGsNtxmswb5rklmOYgTRJ4lfrTuyyMyPSKJzqIPzyvxGhFc_fo_vuZ8V0WB5jj7MIBqYpk_SRjmO7XpKz6aaqFKucEhbzUwu9nhp_dZLopdh_zKb8-?purpose=fullsize
 
https://images.openai.com/static-rsc-4/vKu2mH7m0Q-uVdeB7yB5xNdfusNwUXck2aMF8xaFye752DhGFs327S5AU5lSVqUY_qloH9-40B-rvDAuHs95vKOZ5I4D7moHSVsvT-CB9keawsaNsimVLocZRJP3F9DXt96W0-nsF1bb7iuGDnnIx2OJNccnVvLkKPdk6ag_u7FFpuWncAjNhQJgPgI4cCiK?purpose=fullsize
 
5

Learning the Prefixes

The first four prefixes are especially important because they are not as obvious:

meth- = 1

eth- = 2

prop- = 3

but- = 4

From five onward, the prefixes are more closely related to familiar numerical prefixes:

pent- = 5

hex- = 6

hept- = 7

oct- = 8

non- = 9

dec- = 10


Determining Carbon Atoms from the Name

Once the prefixes are known, the number of carbon atoms can be identified immediately.

For example:

hexane

The prefix is:

hex-

Hex means:

6

Therefore, hexane contains:

6 carbon atoms

Its molecular formula is:

C₆H₁₄


Another Example

Consider:

octane

The prefix:

oct-

means:

8 carbon atoms

Use the alkane general formula:

CₙH₂ₙ₊₂

For:

n = 8

Hydrogen:

2(8) + 2 = 18

Therefore:

octane = C₈H₁₈

https://images.openai.com/static-rsc-4/HEQmV7Fcx3BL3o5IcCft_UT62bSvxtV-rEYS1-Tx1G-PE7W1Qa79zlJKJ352qEL03DTcEpa2OIeXC0oN9eALGwsizJujJl_kXlTNU8V4a3zhMB9EwVsvDfiTSA5Kqucog6jzfniVD8wUmYoRqHDrjTG7KcLzCxKIXBYal7GZ1kDm3kytScOXdbZ5FTKh7bV9?purpose=fullsize
 
https://images.openai.com/static-rsc-4/sWebX0GhlkYWAxIgTaHd3kIwemYSj-CNG0i3Na1k1ZmKbuRk78jyypdvzXGsjE18byMEQND1ioZUbKLGsNtxmswb5rklmOYgTRJ4lfrTuyyMyPSKJzqIPzyvxGhFc_fo_vuZ8V0WB5jj7MIBqYpk_SRjmO7XpKz6aaqFKucEhbzUwu9nhp_dZLopdh_zKb8-?purpose=fullsize
 
https://images.openai.com/static-rsc-4/tTh1pRy7vye1NcWtFjZB51Fm7fc-aUWxR8J8LzDGGLtV8cRR-T-KNt4oTiKG9I65GH0u0nSp8nXnERquHLYJeaNdubM3so_YNYzzG31rzVGCVQW4-LyteNpSvBwbOVrq9qw2H5_Yo_YoeuCeW02ob8p45sCP0caEcdQYgwOjq-JwtehhL11PaVKalJvuD3b1?purpose=fullsize
 
5

Writing a Molecular Formula from a Name

Suppose you are asked:

What is the molecular formula of heptane?

Step 1: Identify the prefix.

hept- = 7 carbons

Step 2: Use:

CₙH₂ₙ₊₂

Step 3: Substitute:

n = 7

Step 4: Calculate hydrogen:

2(7) + 2 = 16

Therefore:

heptane = C₇H₁₆


Writing a Name from a Molecular Formula

Suppose you are given:

C₅H₁₂

First check whether it follows the alkane formula.

For:

n = 5

2(5) + 2 = 12

Yes.

Five carbon atoms use the prefix:

pent-

Add:

-ane

Therefore:

C₅H₁₂ = pentane


Straight-Chain Alkanes

The simplest alkanes have carbon atoms arranged in a continuous chain.

For example:

propane

CH₃–CH₂–CH₃

contains three carbon atoms.

butane

CH₃–CH₂–CH₂–CH₃

contains four carbon atoms.

pentane

CH₃–CH₂–CH₂–CH₂–CH₃

contains five carbon atoms.

https://images.openai.com/static-rsc-4/K1jSE_sfMbCs02HK8Yg6fnA9BqL_OI9WfK9LkANGzacGb-Kb8roY4MgxqMjTo8xFvWaS-TBk2XO18MQJtcuaJIxdg3JCdyYw2T13jC01VEA6KAaYuTftHbcPQu95fIZSvuT9hFuRnz2XjIlXv6r063Pf3s7Js5wUi5Wt7V2uQyADI-NkhwRtyJ_NKZTaiTCN?purpose=fullsize
 
https://images.openai.com/static-rsc-4/ClVOvmfk-vsfrrU08_16Qd5QzWf17KIr_VZvPCt1vOLiHXw3mOP2l_WiLkSoW4dDRF9yucq6bnaPDXietoZm1cBCHw5XWn7pXgEAyiu__Qrr4UH3UE-UOT-H6pY7LlZzCASbK2t_yhZd7UenCks3P9xB7KKGvBsPyCPWe4U57CqLYKYGOHhsolc2S9LKEIgF?purpose=fullsize
 
https://images.openai.com/static-rsc-4/6mMxo3a_3jvaR1IBnR25RS2aaaQ5BqfuesPUgRrbgxic-rY2fMaDdsMcZVvZ00xUWfx9N7y9eNNWV0iTQqBoXljr3qMyanoTNzcj62_JVMsFpl4G_9nIVX46dpavccxpVlX9io_YawI-s51drIiNGh1nh-UCyndCMh1kNVf4HJky52bpEdXmCBhf_OLOTmXF?purpose=fullsize
 
4

Count the carbon atoms in the continuous chain to determine the basic name.


Condensed Structural Formulas

Organic structures can be written in a compact form called a condensed structural formula.

Examples:

Methane:

CH₄

Ethane:

CH₃CH₃

Propane:

CH₃CH₂CH₃

Butane:

CH₃CH₂CH₂CH₃

Pentane:

CH₃CH₂CH₂CH₂CH₃

Each C represents one carbon atom.

Counting the carbon atoms allows us to determine the alkane name.


Naming a Straight-Chain Structure

Consider:

CH₃–CH₂–CH₂–CH₂–CH₂–CH₃

Count the carbon atoms:

6

Six carbons correspond to:

hex-

Because the molecule is an alkane:

hex + ane = hexane

Therefore, the name is:

hexane


Why Naming Becomes More Complicated

Not every alkane forms one straight chain.

Carbon atoms can also form branches.

For example, the molecular formula:

C₄H₁₀

can represent more than one structure.

https://images.openai.com/static-rsc-4/24aoTMyVPpHfLV8Pr4kkY_3G2-IwIbT14xBDfAY8pv6gax9_5IphL8QVJAakFMKTwwFdZrT1h4rz9iBapLorzzHdKXEgvzZGF1t40iKOnY6KeqYwIJWodP60nc_ENgVXfTfVf9tO30OVt44w1brm3b7AD1rZKjY5nYYQ2q0kvfhRZQ3gfl6eR6ctwXBl5saT?purpose=fullsize
 
https://images.openai.com/static-rsc-4/qnbRdGzFRnA4SZS2-vZ5CItGOfjUqwp-50VH-zffU4fCbvVwG5Yfb69dO1DnhH-mmYwJdGd9YcZoTQa99aWuLN3XzWuojujUCzFAckucxAplAruaDMG1geeqcYHew0V8jFRmT3U2AQlKlqu8Tmce3_eZw9U7Ii2Tt1dS8PAMwS_KbZpgCduONH-VnWXw-p6F?purpose=fullsize
 
https://images.openai.com/static-rsc-4/qTeJ3kx8h3ABkg3R7SYL5btj9lslKLRBt3BFB0WyZUEw6k-vDIDYi0HI0EWzCFoT2OWulfpuxDVyItp4csanBrntegJuBcBuAGBdhIZ6bo5kQWD7R5jof_Vza5xxHnEslm5VS2z60UB6MB4gnWPK_BwodGxxJHqgROMHw1e3_vXhw4Gz4x4eijd8rJpZdvN_?purpose=fullsize
 
5

One structure is:

butane

Another is:

2-methylpropane

These compounds have the same molecular formula but different arrangements of atoms.

They are structural isomers.


Naming Branched Alkanes

For a simple branched alkane, use this basic procedure:

1. Find the longest continuous carbon chain.

2. Name that chain.

3. Identify any branches.

4. Number the main chain.

5. Give each branch the lowest possible position number.

6. Combine the numbers, branch names, and parent-chain name.


Step 1: Find the Longest Carbon Chain

The longest continuous chain determines the parent name.

https://images.openai.com/static-rsc-4/l0L-WdM2b8plIhWxWLvikk5WFtQ9b6PWIO7ESr9l0QQf1ODnfl00SALLNC9iK-q5fvusaS9xnTKrAu8yHeMVBKel-P68VZ_ePo1Pq9a14z5Nrpz4vZD86Bqyauwj7U9nGc10lasQY1AKtQ09E7jfAUorzUJI84gMk_ekhAICFStkKfcYLP9sUgjw043x9bbn?purpose=fullsize
 
https://images.openai.com/static-rsc-4/dI_OUtUhsk1I9jfsT9c_fjRVc8YExONSgtPWfnPdaZ2Ftg3v4zSU-STQgg6WWBburqP9a4eMRwhH40rmKIMqJ6qql8V1jkLFAYQhSJ5Q_X6NbS8ssb9OBwjyNKySsC2q8mBMFzYPDLT-DECrJKrGPtoixgVxYyQw3ykkCJ40Dbd5C5b6jLPBOarkSkZ42k9N?purpose=fullsize
 
https://images.openai.com/static-rsc-4/tKBJB9NOqRHTt_aZPvUGjLGg4a_CMObALLEy2oRYbEfTs6Cdqbm5GRX5bt8zrByHlglGnxqdWYzOArdLOb6D71BiIFx9z4BNjfTRu4bx6dZADSrIj1q_w2BvKQKc2fN4ODNt3bSWL9bPC9y-GkwYXislVCfnlpWNYYkEbWEkhWUu5kLTrJO-q75ShWOxwcae?purpose=fullsize
 
5

For example, if the longest continuous chain contains:

5 carbon atoms

the parent alkane is:

pentane

Even if the entire molecule contains more than five carbon atoms, the longest continuous chain determines the parent name.


The Longest Chain Does Not Have to Look Straight

This is an important rule.

When a structure is drawn on paper, the longest carbon chain may bend or change direction.

You are looking for the longest continuous sequence of connected carbon atoms, not necessarily the longest horizontal line on the page.


Step 2: Identify the Branches

A branch attached to the main chain is called a substituent.

Simple alkane branches are called alkyl groups.

They are named by changing:

-ane

to:

-yl

For example:

Methane → methyl

Ethane → ethyl

Propane → propyl

https://images.openai.com/static-rsc-4/Gas2SanyEp1_bOjFDXsn9C9MfqCEhEvvJo8SMI-o1Wf7y0czjVkT5IrV7jT7ozIkS3V85fDGoAuWYxU9BZnuGMSVHtIg_mITEc41yML_uYYdSMaIIAxFVkUS-M8MNqldoQ3NkdDJEIhNUvhPcpdqxYwgJZp3PT_C_4JOX_R1paArK1O5dmiV4OQdgCoZN7yc?purpose=fullsize
 
https://images.openai.com/static-rsc-4/65nedJIGW-OqRIrBdhmHQhFkcU3nHFhtkSzXhE7vPFMXIK6pJaAOsXQR0XKbWqSFvnsrXt_p6-KAMemsij-m4yAUOw_oOX4g2QzE-BZBncSFAi750nqD-Eha8DXthsT7n9qB1-ElRUO8fSOUEvq071ltXV5a6oiKPe21_RkMUgktekr31PPK3UuoAQ7hun3r?purpose=fullsize
 
https://images.openai.com/static-rsc-4/gPCMEpq9SNuBr5_Jmbg6x4t1PcBqqAcrSBvPJljceRcl0iN__nPPoQruTKgr9MqFs5_DehFI9SYtHkgQZI22ub0jgVbOgc01jxDO-obBMdHFB0louYSdnUrSUex_bBuXbvM1drFrkNv2pYtA5o64zUGg3c1jJyYekRqKMGPFk5Sx2zMSDDbuKcw_ca-kAeyd?purpose=fullsize
 
5

For introductory naming, methyl and ethyl branches are especially common.


The Methyl Group

A methyl group is:

–CH₃

It contains one carbon atom.

If a methyl group is attached to a propane chain, the molecule might be named:

2-methylpropane

The name tells us:

2- → branch is attached to carbon 2

methyl → branch contains one carbon

propane → longest chain contains three carbon atoms


Numbering the Main Chain

The main carbon chain must be numbered.

Number from the end that gives the first branch the lowest possible number.

Consider a five-carbon chain with a methyl branch.

If numbering from the left places the branch on carbon:

2

but numbering from the right places it on carbon:

4

choose:

2

https://images.openai.com/static-rsc-4/H_K26rCB36jwbsSjLukzhdEUtGxMoEem2_qCzNKVDBBP2f_zldJaYQkeotrg7o9H9nlHiertJdVyFD79OSDW0fzyMqgSiFfoJcBo3KtttoFEitgFiphk-QcT4XjISI4IizB76y4YSE6i9AKSM2PvBC8hTQ04310L5JmF-KhUV4ef3DCpDrpcUPeGvWyuyRBo?purpose=fullsize
 
https://images.openai.com/static-rsc-4/8mZ3zPFrtVSxgkyYArL0a0DFzuS3GqSnR4vCrExK4RZPpOdXAOQDxduK8pKyen_GRPMKlv_IwBWQOY812AY52qekZpUpD9za2X50jl0AMySDhGWknR-rmkGnCi0GUhZ6gVb_NRe3CG8uy9FIIluHk8MFKDlZhPF1S5R7vC1r6I5Hkb7M_qTh0o-fv50W7sXc?purpose=fullsize
 
https://images.openai.com/static-rsc-4/gPCMEpq9SNuBr5_Jmbg6x4t1PcBqqAcrSBvPJljceRcl0iN__nPPoQruTKgr9MqFs5_DehFI9SYtHkgQZI22ub0jgVbOgc01jxDO-obBMdHFB0louYSdnUrSUex_bBuXbvM1drFrkNv2pYtA5o64zUGg3c1jJyYekRqKMGPFk5Sx2zMSDDbuKcw_ca-kAeyd?purpose=fullsize
 
5

The correct name would be:

2-methylpentane

not:

4-methylpentane


Example: 2-Methylpropane

Consider:

 
    CH3
     |
CH3-CH-CH3
 

The longest continuous chain contains:

3 carbons

Parent:

propane

There is one:

methyl group

attached to carbon:

2

Therefore:

2-methylpropane


Example: 2-Methylbutane

Consider:

 
    CH3
     |
CH3-CH-CH2-CH3
 

Longest chain:

4 carbon atoms

Parent:

butane

Branch:

methyl

Position:

2

Name:

2-methylbutane

https://images.openai.com/static-rsc-4/LPJTquWUeZ-yY5Nd42F2n3PUHx6RoPRDySTD_vur9W-hOkmFt_xydtD-aAA-d3tNfyzovcBhvGUIVyDO_q5q3kpeUpXfclDKZhaOMYZ1VsrNjLW9mvjX7MAjpzeA3c5UvAjWTU-CpyTpg7t45wlCtWbl_xSfI9BJntzVSkwKmKYRuET_TD2SlfmUEPW0ZSEY?purpose=fullsize
 
https://images.openai.com/static-rsc-4/BEOF_gHqixjO0eCoYfUDTFBslEET55aAz0scbW-KuEYlCS_zGfWnW-gN1J9qTqUSYpKeVZkuY9x-Ozm-A4UXoE1vYzKt-4juIgzarFPpTNl4iBVjH1eyE-d_18QOREdDuzieJT3Tnd4IcRhw17kPF8NH-pn3AuhQe3XbeyXaaXNtbsXYWCt_ox2q9VfPKwFQ?purpose=fullsize
 
https://images.openai.com/static-rsc-4/FYa39j68194PYocTuKPuXXxcIGhLKjLXAppvM7Lh52DfzFwacHIZuQM5itFnsK8liQaHNL71PpfJgMdBzz1YzL5s6jxf1BRYz9HNXPL4Hw-TRHfcTo8393bVCoTqjyZzmwfG7KR8bB6IP_DrYtQbuUO5B5Crt2Iu9NM-iQ-WWyuOszRy50mhqIr_hhzlXPcw?purpose=fullsize
 
4

Why It Is Not 3-Methylbutane

The same structure could be numbered from the opposite end.

That would place the methyl group at:

carbon 3

But IUPAC naming requires the lower number.

Compare:

2-methylbutane

and:

3-methylbutane

Choose:

2-methylbutane


More Than One Branch

A molecule can contain more than one identical branch.

Prefixes are used to indicate how many identical substituents are present.

di- = 2

tri- = 3

tetra- = 4

For example:

2,3-dimethylbutane

contains:

  • a four-carbon parent chain
  • one methyl group on carbon 2
  • one methyl group on carbon 3
https://images.openai.com/static-rsc-4/XqycVeCogis9uxPxxk1HVOYtWQevx1berjxUIp6-5GiQ08rOhO4z1aG9BeJ1otlrLolqsYB33h_o4KvPhKCOGryevHI_uztYNzOKZ-bTMGtggtiXy3POjZVJ9sChkiKfPB1IZpSnaZUoHZWIkPGRYUqufZHNgbwLrKHVKdSxBuadzKMnVGXXTOAzs7hggQWI?purpose=fullsize
 
https://images.openai.com/static-rsc-4/igTbhFMOxYCNuFfo7vzmARAJCqgv3HBDQSe6gTEpqtKUD4P952N4VIMi90soXE2s4AgehP8Xg6MDqH0aB29_7WuQfc-qb6irKqf7BcgJNyj9PwbUhRc7uo30eQlM3Xvul9FQc2Ca4bsq-LzOuMIt902JvxNiQ9PoVCctxVAFFL8B5slsbiirUVWEOWr4J-Mn?purpose=fullsize
 
https://images.openai.com/static-rsc-4/q6mwlnDMb_P_HhHeWLSih76MpbAMV9XCJFAoUstI2y4mXDdrOqaCpn2fdO2oOrVQszJpQqZuj0y9FrzwJCJGce3AT0c6SZMOz5TQdi5kFu0wt_WQo64dEvTclp5tXowZqyZRN_NSYX1e7E614XD1_8uBOpoLmhHBrkKNVdIMRob-_wwSYMYx9PAILvxAW7mL?purpose=fullsize
 

Example: 2,2-Dimethylpropane

Consider:

 
      CH3
       |
CH3 - C - CH3
       |
      CH3
 

The longest continuous chain contains:

3 carbons

Parent:

propane

Two methyl groups are attached to:

carbon 2

Therefore:

2,2-dimethylpropane


Writing Position Numbers

Position numbers are called locants.

When more than one number is used, separate the numbers with commas.

Correct:

2,3-dimethylbutane

Not:

2-3-dimethylbutane

Use a hyphen between numbers and words.

Correct:

2,3-dimethylbutane

This punctuation is part of the systematic name.


Different Types of Branches

Some alkanes contain different substituents.

For example, a molecule might contain:

  • an ethyl group
  • a methyl group

When different substituent names appear together, they are normally listed in alphabetical order.

For example:

ethyl

comes before:

methyl

because E comes before M.

https://images.openai.com/static-rsc-4/l9Jn0eZTDmskt07eMLnf1d9RMF_D3lOJ25vEYYadl-1zXnG7oGRG1JTNTxYYEc4BETnyPbpWMxpzehvc_V9IHTn_wpMLI1zjwhuaNCCgqXCYlBU25oRwjZmtgfzzOfSVA5IXLD_hQfCfoaSj5yUixSnkc5OKT72VhlB8v8OprPBL8Qx2MYpWzFwJDvuxAT9z?purpose=fullsize
 
https://images.openai.com/static-rsc-4/gLzN-dcmiPS7RDCp3TuAUgpVxTNUECTFKqzoEMIgmNl19ZIbagdXbU7wHUbKWKfdVBzTCXfz28qL4nrjfe3Tw16kuZafZ1bt45NSf_fXKBk8sEI5hlnCGIJQIltrUvOwfhwkmU1Uqq2ZlS7y_XQT54x7z24JfM9g5YXs-OjCJ4cfX-e8OtgxXSR2zxTTtQBv?purpose=fullsize
 
https://images.openai.com/static-rsc-4/Bw4wGGT9IK_2IIP3kIdSm59zr9Y2RNJ4vGRPkQHOTGN8IUQtg0-9faAqEiTQT-V6Z-Yg4rNni7_s6Naylygxl_SJVl7oftcDPWH_NaYxuhu9Z1UQSRFRVijNZlSNoZVacpH9sEaWWEa3ztZ-galuZulDE8zOBws2ccBBiGGIvXLNNFyrsOP2S_OHqhaGGBZ6?purpose=fullsize
 
4

Prefixes such as di-, tri-, and tetra- are not normally considered when alphabetizing substituent names.


The Lowest Set of Locants

With more complicated branched structures, choose the numbering direction that gives the substituents the lowest set of locants according to IUPAC rules.

For introductory examples, this often means:

start numbering from the end nearest the first branch.

For example:

2,3-dimethylpentane

is preferred over:

3,4-dimethylpentane

because:

2,3

is the lower set of position numbers.


Naming from a Displayed Structure

When given a structure:

Step 1: Find the longest continuous carbon chain.

Step 2: Count its carbon atoms.

Step 3: Determine the parent alkane.

Step 4: Number the chain.

Step 5: Identify each branch.

Step 6: Record each branch position.

Step 7: Use di-, tri-, or tetra- if identical branches repeat.

Step 8: Arrange different substituents alphabetically.

Step 9: Assemble the complete name.

https://images.openai.com/static-rsc-4/Q6BYyZiV-cmBC6Gs5_zoKm2rvnl93p67f-W4UlroN5wbO_LNrwNkR8tc1iZFggvcnys340sZ4lNwbxJ03hQMyyKRX492QYldExXe1exWIu5I7v74mwKnw1Jq6oRwX14OCkxQaB6e4IIaMh7sGwIOrqFtKWNMi6aIu9HoMz2FpIGBgJoUM24UbyCPf0r9U7Ue?purpose=fullsize
 
https://images.openai.com/static-rsc-4/igTbhFMOxYCNuFfo7vzmARAJCqgv3HBDQSe6gTEpqtKUD4P952N4VIMi90soXE2s4AgehP8Xg6MDqH0aB29_7WuQfc-qb6irKqf7BcgJNyj9PwbUhRc7uo30eQlM3Xvul9FQc2Ca4bsq-LzOuMIt902JvxNiQ9PoVCctxVAFFL8B5slsbiirUVWEOWr4J-Mn?purpose=fullsize
 
https://images.openai.com/static-rsc-4/gPCMEpq9SNuBr5_Jmbg6x4t1PcBqqAcrSBvPJljceRcl0iN__nPPoQruTKgr9MqFs5_DehFI9SYtHkgQZI22ub0jgVbOgc01jxDO-obBMdHFB0louYSdnUrSUex_bBuXbvM1drFrkNv2pYtA5o64zUGg3c1jJyYekRqKMGPFk5Sx2zMSDDbuKcw_ca-kAeyd?purpose=fullsize
 
5

Example: Name This Structure

Consider:

 
      CH3
       |
CH3-CH-CH2-CH2-CH3
 

Step 1: Longest chain:

5 carbons

Parent:

pentane

Step 2: Branch:

methyl

Step 3: Number from the nearest end.

Branch position:

2

Name:

2-methylpentane


Example: Two Methyl Branches

Consider:

 
     CH3   CH3
      |     |
CH3 - CH - CH - CH3
 

Longest chain:

4 carbons

Parent:

butane

Branches:

two methyl groups

Positions:

2 and 3

Use:

di-

Name:

2,3-dimethylbutane


Molecular Formula from a Branched Alkane Name

Branching changes the arrangement of atoms but does not change the general formula for an acyclic saturated alkane.

Consider:

2-methylbutane

Count all carbon atoms.

Parent chain:

4 carbons

Methyl branch:

1 carbon

Total:

5 carbon atoms

Therefore:

n = 5

Use:

CₙH₂ₙ₊₂

C₅H₁₂

So:

2-methylbutane = C₅H₁₂


Another Formula Example

Find the molecular formula of:

2,3-dimethylbutane

Parent chain:

4 carbon atoms

Two methyl groups:

2 additional carbon atoms

Total:

6 carbon atoms

Use:

CₙH₂ₙ₊₂

H = 2(6) + 2

= 14

Therefore:

C₆H₁₄

https://images.openai.com/static-rsc-4/k3khp0k6FZteLvVRa1ST0ltzMJxycA-2D6kNiPeB_NSUxNnXWleR3tlSGQ-Awfu1SW1ujMIb1HqHc910YGIy5sgkKXJx7P-gttUHkMz9bmB-8HNHz9QYc8RdLIEfcgeOGzjrvthaAqqasaDuNo5C8H5iOFYLPR7YEz_h53D-VYCk9zCocUhzoalNQL-wVFWh?purpose=fullsize
 
https://images.openai.com/static-rsc-4/QrR4cqAQyI1Tz7E3-rjTPPN3VZ4fw025LAoGXVfIg8wKp3EbU93akLE8nySSwHxBQnDj_GEKlW0if3lRYyEEUY-NAnTg_3TuWkTDLCYuIwaJhgJXE3IIMDudZ1w0YOsz_aGRBbxksApapJFc78X1g4vIv1EXGO5vz4jKCPNWgK_sqUi6-QNaC2Vs0_xaJfWa?purpose=fullsize
 
https://images.openai.com/static-rsc-4/CnyTEmsOPsHcNomM4SdkQwsTqoR-9xvHtncwJWUHiR_o2clfrUJfQmDYBueuQZmhr9P23YxHrq5vZzxxqyXl99CRBtKPFzgapYAC5Cz3HquXsYHxuKuv8unKnhfRP_ExUM1WHlGKqLFGiLNdBl45j-cAJMQGim76CJWAuLevOIBzJu44pNeMcanLvMqyNQT9?purpose=fullsize
 

Structural Isomers

Compounds with the same molecular formula but different structural formulas are called structural isomers.

For example:

C₅H₁₂

has several possible structures.

These include:

pentane

2-methylbutane

2,2-dimethylpropane

All three contain:

5 carbon atoms

and:

12 hydrogen atoms

but their carbon atoms are arranged differently.


Why Names Matter

If we simply said:

C₅H₁₂

we would know the molecular formula but not necessarily the exact structure.

The systematic name:

2-methylbutane

provides structural information.

It tells us:

  • the parent chain has four carbons
  • there is a one-carbon methyl branch
  • the branch is attached to carbon 2

This is why systematic naming becomes increasingly useful as molecules become more complicated.


From Name to Structure

Suppose you are given:

3-methylhexane

Break the name apart.

hexane

means the main chain contains:

6 carbons

Draw:

C–C–C–C–C–C

Then:

3-methyl

means place a:

CH₃

group on carbon 3.

https://images.openai.com/static-rsc-4/Wsnw_yycFm0GgGU7Aqkz9tmNJIp6NBLmIa_ero3ytn_N025ToGgP_PV9DkqV07ZX8_gkAfMdqyGBZCVvVAmKA28rCP6QpCdiq7wAYWouqH4WtMBaQx8WTG-a1JT_ra1yrEd7idn9-vXKeWUzBPlWZGEcDCAdRlCGK5VzVfIETg5ZFjIvIoLvgCbvoO5THyfw?purpose=fullsize
 
https://images.openai.com/static-rsc-4/fflxVNCR32BismdYmqitTpM6tqtkfl0zH6hAR18eLw8QdHy-Y-IOG8uaLZUgHpLOILjC1jik7S3xjCy0BreUG7QdCQ2DMGx2epaz8WPQIZxENtTWof-Gj9NwZ2DlGcjsHvHBWseRLXRbJDqh0oWAxqrQPVS6XoGT7XZnrGmutP4xtlkfD8UUIt4aidXLyuzx?purpose=fullsize
 
https://images.openai.com/static-rsc-4/CVpe5XqGetlLVgVZ6I39gFb-yp0YpaqYG0uC-IeK10eo5coWf5285OeDdICVCZ4SK60bVngowYHsEYKkEmDuUVZ9CRzAAd_OXuakOeOcQzC642O9M-VqFivSKvcdY_sS2WFjoLqxOMUAnHSVvM-yD8cClISxf-CMb7xQjRTZOEDjyCtnZ1-MSLn4KJit4IOS?purpose=fullsize
 
4

A condensed formula can be written as:

CH₃CH₂CH(CH₃)CH₂CH₂CH₃


From Name to Formula

Find the formula of:

3-methylhexane

Parent chain:

6 carbons

Methyl branch:

1 carbon

Total:

7 carbons

For an acyclic alkane:

CₙH₂ₙ₊₂

Therefore:

C₇H₁₆


Worked Example 1: Methane

Name:

methane

Prefix:

meth-

Carbon atoms:

1

Formula:

CH₄


Worked Example 2: Butane

Name:

butane

Prefix:

but-

Carbon atoms:

4

Formula:

C₄H₁₀

Condensed structure:

CH₃CH₂CH₂CH₃


Worked Example 3: Nonane

Name:

nonane

Carbon atoms:

9

Calculate hydrogen:

2(9) + 2 = 20

Formula:

C₉H₂₀


Worked Example 4: Name C₈H₁₈

Carbon atoms:

8

Prefix:

oct-

Add:

-ane

Name:

octane


Worked Example 5: Name a Straight Chain

Structure:

CH₃–CH₂–CH₂–CH₂–CH₃

Count carbons:

5

Parent:

pentane

Answer:

pentane


Worked Example 6: Name a Branched Structure

Structure:

 
    CH3
     |
CH3-CH-CH2-CH3
 

Longest chain:

4 carbons

Parent:

butane

Branch:

methyl

Position:

2

Answer:

2-methylbutane


Worked Example 7: Formula from a Branched Name

Name:

2-methylpentane

Parent chain:

5 C

Methyl branch:

1 C

Total:

6 C

Use:

CₙH₂ₙ₊₂

Formula:

C₆H₁₄


Worked Example 8: Two Branches

Name:

2,3-dimethylpentane

Parent chain:

5 C

Two methyl branches:

2 C

Total:

7 C

Formula:

C₇H₁₆


Worked Example 9: Correct the Name

A student names a structure:

4-methylpentane

But numbering from the other end places the branch at:

carbon 2

Therefore, the correct name is:

2-methylpentane

Always number from the end that gives the substituent the appropriate lowest locant.


Worked Example 10: Find the Structure from the Name

Name:

2,2-dimethylbutane

Parent:

butane = 4-carbon chain

Branches:

two methyl groups

Both are attached to:

carbon 2

A condensed structural formula is:

CH₃C(CH₃)₂CH₂CH₃

Total carbon atoms:

6

Molecular formula:

C₆H₁₄


A Useful Naming Checklist

When naming a straight-chain alkane:

Count the carbons → choose the prefix → add -ane

When naming a branched alkane:

Find longest chain → name parent → number chain → identify branches → locate branches → assemble name

When finding a formula:

Count all carbon atoms → use CₙH₂ₙ₊₂

https://images.openai.com/static-rsc-4/2ust6HQJ5_hjCzJMNP5USAFL9Lwk6GMugBLhYkohlT24RTwrs1RDS41LL7J29oLpW3VrwVOUCnPqOkLYDn8lbL6poYoG1LbDSv0svi-jESd2uts6uimWxtFGQ658oRBpMs-zQpaz3HZ3P3gMyf5i6qtJHQ1TCllwnXSqUUR4ouysLjx2IpkrmZeRLFo2RrQ4?purpose=fullsize
 
https://images.openai.com/static-rsc-4/QaXC1VumPZ_d6KVSaskZ528qwfMngbcf2Y-3A6bAB5dnOJZFLU4gWRmk8DSSnk85z6xWe8G86FNhIiZhXGDg4unurJUu-03Ts6mQgYt6TJEXalVs4OVQbUblLJimmvzGpJv5hOYpN28glrZyLIxCuz3tdopSBvKAC5LvyAnTkujz5aXtWL2mXc37Qw68F-EF?purpose=fullsize
 
https://images.openai.com/static-rsc-4/x_avC0qJEHW6VWuJ1dM7u4hw8hz261pH8jq2Bu0tzG-DqVFXdIAy-Wdv3kttXpRUPJPOrnc6iPG9BB-OHSQaU_wwwK9Bqn2jWDh4IrA_p5nXwcumEbQH3xczQkgIaEXZtCQfJT9k4PFyoibuJ6GmRsHUf7wxKSWczXdFdIzXCZ5NqoybWTi_yfHnI5tvtvuO?purpose=fullsize
 
5

Common Mistakes

Mistake 1: Counting only the carbon atoms drawn horizontally

The longest chain may bend.

Look for the longest continuous carbon chain.


Mistake 2: Counting the branch as part of the parent automatically

The parent is determined by the longest continuous chain, not by how the structure is positioned on the page.


Mistake 3: Numbering from the wrong end

Choose the direction that gives the branches the appropriate lowest locants.


Mistake 4: Forgetting the branch position

Write:

2-methylbutane

not simply:

methylbutane

when a locant is needed.


Mistake 5: Forgetting di- for two identical branches

Two methyl groups require:

dimethyl


Mistake 6: Using hyphens between numbers

Correct:

2,3-dimethylbutane

Numbers are separated by commas.


Mistake 7: Forgetting hyphens between numbers and words

Correct:

2-methylpentane


Mistake 8: Counting only the parent chain when finding the molecular formula

For:

2-methylpentane

there are:

5 + 1 = 6 carbons

not five.


Mistake 9: Changing the molecular formula because the chain is branched

Straight-chain and branched acyclic alkanes still follow:

CₙH₂ₙ₊₂


Real-World Connection: Octane

The name octane tells us that the molecule contains:

8 carbon atoms

Its molecular formula is:

C₈H₁₈

https://images.openai.com/static-rsc-4/HEQmV7Fcx3BL3o5IcCft_UT62bSvxtV-rEYS1-Tx1G-PE7W1Qa79zlJKJ352qEL03DTcEpa2OIeXC0oN9eALGwsizJujJl_kXlTNU8V4a3zhMB9EwVsvDfiTSA5Kqucog6jzfniVD8wUmYoRqHDrjTG7KcLzCxKIXBYal7GZ1kDm3kytScOXdbZ5FTKh7bV9?purpose=fullsize
 
https://images.openai.com/static-rsc-4/k6XtyF-wf2INzKqnTzIyJLSmZDai4EoV6JELBQoyFmVyCWnMi3vSncs1TrJcVADNFWuWLiCS1b-8UGm9iaaZryquK8mlbmg8hqqYJfnMiFUoHRP85TJFxF_EQU24OkIE8laXaT2kZ3y3kGbqS2CrQzasUS3pEv-JDsFWudJ4ds9X6DAZaBPqZbCPO0OCYQ2K?purpose=fullsize
 
https://images.openai.com/static-rsc-4/VrXYjrYJS2W9t-x8yn3iLJP-NhDKfrjI9-tF3jDU7xLCaDwimts3JU9W8qcgfvKgfq_0ajnmeOqFLEQPk8M5sBo79pnr_tieYVkUHel1JU3lmIYzivl35TduFBGq0GDH7pLIdFR1D9c06uP2mmDtKZ7_j9nlGY5jvhh5wZXmsQZIX3rKQBUMEP8KVmziyirv?purpose=fullsize
 
4

The word "octane" is also familiar from gasoline octane ratings.

However, an octane rating does not simply tell us how much octane is present in gasoline. It describes the fuel's resistance to engine knocking using standardized reference fuels.

One important reference compound is:

2,2,4-trimethylpentane

commonly called isooctane.

Its molecular formula is also:

C₈H₁₈

This provides a real-world example of why different structural arrangements of the same molecular formula matter.


Real-World Connection: Hydrocarbon Fuels

Alkanes occur in many fuels and petroleum-derived products.

Examples include:

Methane — natural gas

Propane — LPG and heating fuels

Butane — portable fuel canisters

Octane-related hydrocarbons — gasoline

https://images.openai.com/static-rsc-4/EFdMrKb0AhOeV7Pti1G-TjkQckR4pRnGj2nFwirl3huB8bV4VYh3eokI0w_skC3ScDnbMrM_p2eSU8pOXH9qJxTdDbfr0p03Mc99__cRSIKqcyO6UxcOM7bpGKC0wFkgliLPSpzaUipMmcTxxM_zwGwJd9CEDrhdS3eEk8mNodY-Kky-XZjdu_Tn79NKVivV?purpose=fullsize
 
https://images.openai.com/static-rsc-4/tGr2zkyvTOqttIi5TsjyCjjNynh2AiV8H0rI1pjcYMuLqgFZkmEjXFHdyUiNy62zUOTFzOOLDCF6iibvpxMiHarKrrdYg3Qy8jg8kag0mt0y9V5wJJV6qzmA0T9BxIoVzR75K32_cPWYJJLtUGxz7IVL8VmNAOtE-QwSRzWhZs-ichMyaUsgFnSRPrtB7frr?purpose=fullsize
 
https://images.openai.com/static-rsc-4/K7QFjPpIVHsysOeCvKe36IFwNtDxvxXLfgBJ4F66ckd_gZaRJK88U1g8is4JpUu-0y9_KHxkGZuHX10sNUfhtn8tY_Lw-1iiJlXdy4vKt6Q7Yl4v7wMNA_DFfxKEbEN34aOY2GxcG5GvzyJcC9ZcyfqI5w2DCM_CRDyo0YcH3Oi3hbdJ38R3HCyMcBaT44Nj?purpose=fullsize
 
5

Knowing the names and structures of alkanes provides a foundation for understanding petroleum chemistry, combustion, fuels, polymers, and many other areas of organic chemistry.


Did You Know?

Carbon's ability to form long chains and branches means that the number of possible alkane structures increases rapidly as the number of carbon atoms increases.

Methane has only one possible carbon arrangement.

Ethane and propane also have only one.

But larger alkanes can have several different structural isomers.

As molecules become larger, systematic IUPAC naming becomes essential because a molecular formula alone may not identify a unique structure.


Key Terms

  • IUPAC: International Union of Pure and Applied Chemistry; organization responsible for internationally standardized chemical naming systems.
  • Alkane: Saturated hydrocarbon containing only single carbon-carbon bonds.
  • Homologous series: Family of compounds with the same general formula and similar chemical properties.
  • Parent chain: Longest continuous carbon chain used as the basis of an alkane name.
  • Prefix: Part of the name indicating the number of carbon atoms.
  • Substituent: Atom or group attached to the parent chain.
  • Alkyl group: Hydrocarbon substituent formed conceptually by removing one hydrogen from an alkane.
  • Methyl: One-carbon alkyl group, –CH₃.
  • Ethyl: Two-carbon alkyl group, –CH₂CH₃.
  • Locant: Number indicating the position of a substituent.
  • Molecular formula: Formula showing the number of each type of atom.
  • Structural formula: Formula showing how atoms are connected.
  • Structural isomer: Compound with the same molecular formula as another compound but a different arrangement of atoms.
  • Straight-chain alkane: Alkane with an unbranched carbon chain.
  • Branched alkane: Alkane containing one or more carbon branches.

Key Naming Rules

For a simple straight-chain alkane:

1. Count the carbon atoms.

2. Choose the correct prefix.

3. Add -ane.

For a branched alkane:

1. Find the longest continuous carbon chain.

2. Name the parent chain.

3. Number the parent chain appropriately.

4. Identify the substituents.

5. Determine their positions.

6. Use di-, tri-, tetra-, etc. for repeated identical substituents.

7. List different substituent types alphabetically.

8. Use commas between numbers and hyphens between numbers and words.

9. Combine everything into one systematic name.


Key Takeaways

  • Alkane names provide information about molecular structure.
  • The ending -ane identifies an alkane.
  • meth-, eth-, prop-, and but- represent one to four carbon atoms.
  • pent-, hex-, hept-, oct-, non-, and dec- represent five to ten carbon atoms.
  • Methane through decane are the first ten members of the alkane homologous series.
  • Straight-chain alkanes can be named by counting the carbon atoms and selecting the correct prefix.
  • Acyclic alkanes follow the general formula CₙH₂ₙ₊₂.
  • A molecular formula can be predicted from the number of carbon atoms.
  • Branched alkanes are named using a parent chain and substituents.
  • The longest continuous carbon chain determines the parent name.
  • The longest chain does not necessarily appear as a straight horizontal line in a drawing.
  • The parent chain is numbered to give substituents the appropriate lowest locants.
  • Methyl and ethyl are common alkyl substituents.
  • di-, tri-, and tetra- indicate repeated identical substituents.
  • Different substituent types are listed alphabetically.
  • Commas separate numbers, while hyphens separate numbers from words.
  • Branched and straight-chain alkanes can have the same molecular formula but different structures.
  • Systematic IUPAC naming allows chemists to communicate molecular structures clearly and consistently.
 
 
 

3. Physical Properties of Alkanes

Learning outcomes
  • I can describe the physical properties of alkanes.
  • I can explain why alkanes are generally nonpolar molecules.
  • I can identify trends in boiling points and melting points within the alkane series.
  • I can explain how intermolecular forces affect alkane properties.
  • I can relate alkane properties to their practical uses.

https://images.openai.com/static-rsc-4/SqeVHiueliExPAQ2CpymfA4gLe_WiYYlC-_ySvpVkelm1deKEOFrTE2cFRbjb_Mwc2bINN51116TZfq88quJVpDhVfv5dpNbIzJmsMILmAi-oZiOySWitvO9fgNHf7WGPa6EpDoMwot75u55gE3QJeaXILcPuSNegfwUx6_wS_GfUDGPppV7kXFwJoLLNyY5?purpose=fullsize
 
https://images.openai.com/static-rsc-4/4fT0EDaQI7bdJuUN_3czjb0LH7-M6fro1y0nXGNVSb8eiD78TTWl8nYf0eOk7Z3cdWqhS6eucKDKS9XW_-AEU05M6LDmmd_xbjaVwxr7cAN7M_rtg71yncNMJJYpbade5R_HCOdexa0DLfOTbcrjOgjiw6p1b3HwY0bBHN52LlhqRYqp4pnW3ProcxIamWkA?purpose=fullsize
 
https://images.openai.com/static-rsc-4/a_yPzKLNND67mZtxx2OrbO5pfrucnmB-XzHi8vwmxl3hvHDWcplvyCDnCPsUa8njJNddMJUPy9Z7JhJKXeQHtm_d-ctndhnbA6pwQRl32SEs2v28ul4tBJkj9OZsfwCRt_Hl6q1pjvgeviHVsAO2CP4APObmjBMui9BXnw4G1SymvlpowC5tQhAE37_fDHTi?purpose=fullsize
 
5

Introduction

Alkanes are saturated hydrocarbons containing only carbon and hydrogen atoms joined by single covalent bonds.

Although all alkanes have similar chemical structures, their physical properties change gradually as the molecules become larger.

Important physical properties include:

  • physical state
  • boiling point
  • melting point
  • density
  • solubility
  • viscosity
  • volatility

These properties are strongly influenced by the intermolecular forces acting between alkane molecules.


Molecular Structure of Alkanes

Alkanes contain:

C–C single covalent bonds

and:

C–H single covalent bonds

Examples include:

Methane:

CH₄

Ethane:

C₂H₆

Propane:

C₃H₈

Butane:

C₄H₁₀

Pentane:

C₅H₁₂

https://images.openai.com/static-rsc-4/6mMxo3a_3jvaR1IBnR25RS2aaaQ5BqfuesPUgRrbgxic-rY2fMaDdsMcZVvZ00xUWfx9N7y9eNNWV0iTQqBoXljr3qMyanoTNzcj62_JVMsFpl4G_9nIVX46dpavccxpVlX9io_YawI-s51drIiNGh1nh-UCyndCMh1kNVf4HJky52bpEdXmCBhf_OLOTmXF?purpose=fullsize
 
https://images.openai.com/static-rsc-4/jmy9s2FY1eqTtGvCR_DnnMVXNgvzaEkCp0oulgMTrgUtbS1lKfN0eOZFH8-r7B-fVMLEuGBhZQdKmpKxJam1BN7Jm9q3kwkkB2lE6c7O7W-AacIB0iek9nEQ25GiIV_N58mOXxC9-wnJBGhv8vx3Wwp7E6TsY4l9MVRI2xTZtfR6yW0UoNwu2DFyOkmSD7LR?purpose=fullsize
 
https://images.openai.com/static-rsc-4/sWebX0GhlkYWAxIgTaHd3kIwemYSj-CNG0i3Na1k1ZmKbuRk78jyypdvzXGsjE18byMEQND1ioZUbKLGsNtxmswb5rklmOYgTRJ4lfrTuyyMyPSKJzqIPzyvxGhFc_fo_vuZ8V0WB5jj7MIBqYpk_SRjmO7XpKz6aaqFKucEhbzUwu9nhp_dZLopdh_zKb8-?purpose=fullsize
 
5

As we move through the homologous series, each successive member differs from the previous member by:

CH₂

The molecules therefore become progressively larger.


Alkanes Are Generally Nonpolar

Alkanes are generally considered nonpolar molecules.

Carbon and hydrogen have relatively similar electronegativities, so C–H bonds are only weakly polar.

In addition, alkane molecules do not contain strongly polar functional groups.

As a result, alkanes generally have:

little or no permanent separation of electrical charge across the molecule.

This makes them very different from strongly polar substances such as water.

https://images.openai.com/static-rsc-4/2rgdm6g0h3FMl3kpr-NgGCe9HF5evNm5rTDmz8HfpqWRraCdZzfce5zE9qt71RH8GHHXrD0Ej6sBXKkP6VzeeCE11wSx1qBF9YC1ZvurdJWAi-ISKCf94KVOtQUV7l0MXJQGdeMfvZFuT8XG9j4RtRp1Gm13LEGEpozkP6HxWb9vZcPugkO7jkQhl0JC0-3W?purpose=fullsize
 
https://images.openai.com/static-rsc-4/TNF6iZd1HfD37p7k8mki91aKBRHNzdbPspMLrBQbVBheszUVmkHNb559rxgcLi2pWOZN_8jmEAWVogp2rfZjCXPQGbXVs7klmiWrgrGc4TIpLY7DGVQOwgGeM7sxnIiQ__ordtq--P0meqU5QwITvgm2pSjV0YQ-Eo0yLDIWKB3Vfbc3lQTTtkJV-CcgZ4CO?purpose=fullsize
 
https://images.openai.com/static-rsc-4/yXgW7jk3H6Rpi5ivAUYhLmMfCxOmhJRPcUjONRKXzkE9J06T-rcrkoRMojFy-a8OQkzJWGpQSI049BxQ1IkRDGxk5ypf9jRGl3GDVFzBsEs1_c7hAGyaolQ3rudZoAJ-XxwBhGgoXyq0yQaB1r-GweDvTwB96gG-RD8xHRzwPo6oliJ_wqDMJN5zMGH2bb5C?purpose=fullsize
 
6

Polar and Nonpolar Molecules

A polar molecule has an uneven distribution of electrical charge.

Water is a familiar example.

A nonpolar molecule has a much more even overall distribution of charge.

Alkanes are generally nonpolar.

This difference has an important effect on properties such as:

solubility

and:

intermolecular attraction


Why Alkanes Do Not Mix Well with Water

Water is strongly polar.

Alkanes are nonpolar.

As a general rule:

"like dissolves like."

Polar substances tend to dissolve more readily in polar solvents.

Nonpolar substances tend to dissolve more readily in nonpolar solvents.

Therefore, alkanes are generally:

insoluble or only very slightly soluble in water.

https://images.openai.com/static-rsc-4/J2JuP__xfknzckQhI1PQI3fHeucSZEEdAleIAyIiDa_32jUub2DA0UZEUoahBg6V2D1UFLeHPO7gEuB1BHYl9y6NHfdkrSg84vMuxEoAjz6zcLSyokZrdGoOhSzPez4Gyo-JpcfF0gIhCT04pNr-wmxdvb7YDIHaLVHrh933q_G3OLDERZlFCyfskJlRNP6w?purpose=fullsize
 
https://images.openai.com/static-rsc-4/NtwAwPD_k9XlnjlDxFATpSD_c02yXb77iiN6gEHhouHx3DqLP7pXL1XYT3KLTHJBvU-zZiAaPq3CBluFh3-pSkLe8T5-GRnq1K6oL3tOkaHFPMGoJV_SSQekdDaVK1_PAe32TGtMk4A5Fm912qwwLK9l-7yX0L4xGqDZoIk3QItNqsAuouDV9CWVbghZkcjw?purpose=fullsize
 
https://images.openai.com/static-rsc-4/CN20PL1UWhz0f197wpWoMT_wn44O5ymxxoz9XJEIVCIF8P2rFKbxUATOfl5lFietXB28SSz-OzKwCbeDFCAnacNgHBkvmOjL5C4ijQaoTGvjr31VS_jtvKbaKBxm1-crEeM7gWPrtQCU2JGKdgQcnCfBtVwU6X1qz_ROTMLx0n443dTe0QD9SIccAm3x_5IJ?purpose=fullsize
 
5

This explains why many hydrocarbon liquids form a separate layer when mixed with water.


Intermolecular Forces

The atoms within an alkane molecule are held together by strong covalent bonds.

However, separate alkane molecules also attract one another.

These attractions are called:

intermolecular forces

For alkanes, the main intermolecular attractions are London dispersion forces.

These are also sometimes described as instantaneous dipole-induced dipole forces.

https://images.openai.com/static-rsc-4/9bZZlhtuMIfESfVKnsvN-_h3yj5t9BOYNumSGjCUiHyE2iRtBa5avlwz04xgW37jxm4UKthz8MX9HUPsQCi8jYO18EQMFvNURctVlYRX0wiIPauUkU8OOIzj6fwFKVswHYNg277aVi4xUIh7N0YHCk4M1eLeCkQffYawB_Zz0qiwzdyWG8lznG20b1oMTFpS?purpose=fullsize
 
https://images.openai.com/static-rsc-4/RT-jcLQg1Qou-UiHO-MjU35X9ynnppUK0taV57LOPX59hN4A_z1jpMq0Xhw2s1JHmo6NV0vcXDI77rmUGsupn5aspVQ-FY5Tn5-zapDxm9L1aRXxYZCm_zVTYjPtnRRNRCuLvv3vgKoNXKAI0NsFBUvLMfHVM9DDlGqn7HdQ4o6K-z3XilQJzDJTrbqg0nBr?purpose=fullsize
 
https://images.openai.com/static-rsc-4/NX-9VCZSLmag-D1vA06wYNqtfETssiNQi9M9moz9ARpPm2MEZm7qNstrVDX6rsRdS7KX6ArlPmktKV9eFe5OPEgE9TkL8DqbD14-N3C8sMQOWws5Ubk9HmfQ9u0BiFCROuE0ibMYbUG-ER1gBSqGY9BL7EGN2aisQvStiYWFVWQI1pUt-TcY_l4G8k17haP1?purpose=fullsize
 
6

London Dispersion Forces

Electrons are constantly moving.

At any instant, the electrons in a molecule may become slightly unevenly distributed.

This creates a temporary:

instantaneous dipole

The temporary dipole can affect the electron distribution of a nearby molecule, producing an:

induced dipole

The two temporary dipoles then attract.

These attractions are London dispersion forces.


Temporary Does Not Mean Unimportant

Individual London dispersion forces are relatively weak.

However, many of them can act simultaneously between molecules.

Their combined effect can become significant, particularly for large molecules.

This explains an important trend:

larger alkane molecules generally experience stronger intermolecular attractions than smaller alkane molecules.


Molecular Size and Intermolecular Forces

Consider:

methane, CH₄

and:

octane, C₈H₁₈

Octane has:

  • more carbon atoms
  • more hydrogen atoms
  • more electrons
  • a larger electron cloud
  • greater polarizability

Therefore, octane generally experiences stronger London dispersion forces than methane.

https://images.openai.com/static-rsc-4/FiDQ5Fk4H_RVmSsZtB0iq5i-TUUIdBm-iBR8scZUILtRD_bo8az7jRWkY66HfZ55l4_QgpDVqBXeAA-BvM1Tu-Pn30Rgh9KfHn_B8WSBMZDPjmaKdR0eH9kE3i2DUfd9bOycBUNoWnwpKna_DdCS3JYcj9x8QReVHeF6HaMBovbQiQw8sp5Ubl-p-j0uRs1_?purpose=fullsize
 
https://images.openai.com/static-rsc-4/9bZZlhtuMIfESfVKnsvN-_h3yj5t9BOYNumSGjCUiHyE2iRtBa5avlwz04xgW37jxm4UKthz8MX9HUPsQCi8jYO18EQMFvNURctVlYRX0wiIPauUkU8OOIzj6fwFKVswHYNg277aVi4xUIh7N0YHCk4M1eLeCkQffYawB_Zz0qiwzdyWG8lznG20b1oMTFpS?purpose=fullsize
 
https://images.openai.com/static-rsc-4/yR530B43ncqoZRY6zQgTwl-5RTxp1uJ9jHBMM9tXvG4eKUvzrBBgcjJupiAjgmDybT1ho-yJ2ezT8tSgkmVpHLDS3f3WPISOFasPVTtwcQpzsrsqUXnOqgFwTD1Fqh3kDIUHVmxbICnIOVu3276xaV670V7c2JCIq5qFwtclQrZwvBwM-npYk6xurSkAf00i?purpose=fullsize
 
6

This difference affects properties such as boiling point and volatility.


Boiling Alkanes

For a liquid to boil, molecules must gain enough energy to separate from neighbouring molecules and enter the gas phase.

During boiling, the intermolecular attractions between molecules are overcome.

The covalent bonds inside the molecules are not normally broken.

This is an important distinction.

Boiling is a:

physical change

not a chemical reaction.


Boiling Point Trend

As the number of carbon atoms in an alkane increases:

boiling point generally increases.

For example, approximate normal boiling points are:

Alkane Formula Approximate Boiling Point
Methane CH₄ −162°C
Ethane C₂H₆ −89°C
Propane C₃H₈ −42°C
Butane C₄H₁₀ −0.5°C
Pentane C₅H₁₂ 36°C
Hexane C₆H₁₄ 69°C
Heptane C₇H₁₆ 98°C
Octane C₈H₁₈ 126°C
https://images.openai.com/static-rsc-4/4fT0EDaQI7bdJuUN_3czjb0LH7-M6fro1y0nXGNVSb8eiD78TTWl8nYf0eOk7Z3cdWqhS6eucKDKS9XW_-AEU05M6LDmmd_xbjaVwxr7cAN7M_rtg71yncNMJJYpbade5R_HCOdexa0DLfOTbcrjOgjiw6p1b3HwY0bBHN52LlhqRYqp4pnW3ProcxIamWkA?purpose=fullsize
 
https://images.openai.com/static-rsc-4/P0s2_feI9c4Mxhjkfxir1j_hDrGiDDqi7cjuei0QrDgP9ckDY_5qrT6LQ9R06tXYd1tOpW5cbTwZglzl8AIcVrz2Siiz6dlOV2Lkj9hcCf4i4RovXA0ndvnFJu3-BMF6UbJhK4rD9znrDKWnAr9heDqgGnLE3Vq7vlQGTc3onwbUgCIUWJpskzyU42gws0Cc?purpose=fullsize
 
https://images.openai.com/static-rsc-4/1l5WOJO83-ldbtoP4uR-dtvvFmcjmGcoWqOjtYwXtuAL3eKZXcN0EHIjRbL4mtUHn4mdaYCWNjDiNCzrYjOv5FDvVVQwydmQwheJz4h7crDhg8MADzMPCkr4FEqyg3HNKgLl9i4kBpGWMkzIygawDAPGUE3jgwUB4imWupcdcpqWu4t9wc9ExNJrE-GFRZSQ?purpose=fullsize
 

The overall trend is clear:

more carbon atoms → larger molecule → stronger dispersion forces → more energy needed → higher boiling point


Explaining the Boiling Point Trend

Suppose we compare pentane and octane.

Pentane:

C₅H₁₂

Octane:

C₈H₁₈

Octane contains more electrons and has a larger electron cloud.

Its electron cloud is more easily polarized.

Therefore:

London dispersion forces are stronger between octane molecules.

More thermal energy is required to separate the molecules.

Therefore:

octane has a higher boiling point than pentane.


Chain Length and Boiling Point

A useful general relationship is:

Increasing carbon-chain length → increasing boiling point

https://images.openai.com/static-rsc-4/7EHjnSrCKft7h6RLBd5WQjpPHzWcjhCjWl7Az40RErgvYMPGXBXvba6aQlq0vtTRty45fBXQvGDsaq-UWn5lLfVvpLdtCkqtnwotHjSM-h1exiyonmRpi6ZJ6bJrZRCom8a3lP9TW1wjRVSBMc5BBM683isZDHbsQx20RRQapKoJfwCHRkwJHSRkZcX6Xrbq?purpose=fullsize
 
https://images.openai.com/static-rsc-4/9bZZlhtuMIfESfVKnsvN-_h3yj5t9BOYNumSGjCUiHyE2iRtBa5avlwz04xgW37jxm4UKthz8MX9HUPsQCi8jYO18EQMFvNURctVlYRX0wiIPauUkU8OOIzj6fwFKVswHYNg277aVi4xUIh7N0YHCk4M1eLeCkQffYawB_Zz0qiwzdyWG8lznG20b1oMTFpS?purpose=fullsize
 
https://images.openai.com/static-rsc-4/suVIIuPCMc-CJg6YQbmE3zXsoRcM5sI_v_rnlKiiWle_djW_NFDNjEGa6LX_y9wC1PioDHe7f4a9s3fbgF1PVJysZNZGMVypCcAH0t09m9CFItqJGP1M3kZ8kfcs0f0a6rrfA1oXv8UWrw4eGPTwe9STnJloudgf7kzN8SAQV9yqw93RVWcx2xrrUVYi-p0z?purpose=fullsize
 
5

This trend is one of the most important physical patterns in the alkane homologous series.


Branching and Boiling Point

Molecular shape can also affect boiling point.

Consider two molecules with the same molecular formula.

A straight-chain molecule generally has a larger area of contact with neighbouring molecules than a highly branched molecule.

Greater contact can allow stronger overall dispersion attractions.

Therefore, among many alkane isomers:

greater branching generally lowers the boiling point.

https://images.openai.com/static-rsc-4/taE4OJKlNSzL9sdUiUq7ldJv4gQyZBQ5ZIQ0oXE0F8G4l47_PSN4_zEWY6-Dwvq3BijXIaWNW7xt52YNULCFY7quWUFXZx-7Mf7rj6o2plPw1gQjJvyI1Os2dXqWKpTbjSSVtfcjTcu4L9kMMJjsTsZf0OgfIYtLosAUp1jGC5N_VXtHSDVNusd3AozvWGEE?purpose=fullsize
 
https://images.openai.com/static-rsc-4/vRFX73EieihxeD8x3sbTdDUGRRwWWV3URm7aQQMlyXtY5nWePyfwwR70uyE9gmIAUyp1v33EycZ8aOXG3nU_RSkbEU9-eeUv2okkzJPIQe2i0bJfST5UM4BzF29pt1vB-2lJJR_zGVF9Qw8y3cBkGz0j3CMy3Quv1YACvZzG2Kc-HPuf91TeoRgVeA0Dy7Je?purpose=fullsize
 
https://images.openai.com/static-rsc-4/6XI9H6POHeBGOYBz5HqLrD31DQNzmN6aa92qFuSKe-TgSiAIyDpYY1z23pWFkAk8tnfBtXlfKyZfBhUVSZ_PrbA4QcaUdWPZ3cp5hehDgxhfMUERnqJEoTx6qs6FlGIWBsbvfSOY5DF6MrpJjsxfZThwvrVJljEyiZr3vhwS_I6Py1Kn5hb3Fek_Fo8UKSQp?purpose=fullsize
 
5

For example, straight-chain pentane has a higher boiling point than its more highly branched isomers.


Melting Points

The melting points of alkanes also tend to increase overall as molecular size increases.

However, the melting-point trend is less smooth than the boiling-point trend.

Why?

Melting depends not only on intermolecular forces but also on:

how efficiently molecules pack together in a solid crystal.

Molecular symmetry and shape can therefore have important effects.

https://images.openai.com/static-rsc-4/PblKzBahufzyiD7QM6BewvgS7CQQRf3CR30ZV7PNvKZTvvJObbQpxF3qzCQymvH6EYyO6Md8e9gcUUnidbk_v-d84BOXYNk7OxWExZCqHOzE3ox1GQoVKadJQ9ZFmpXVXG5yxjbaM0w66gMmbyCqk28_aUAhIT_e0KPscjkXYaP8cjrc5HgF_XxPNiZK2OPJ?purpose=fullsize
 
https://images.openai.com/static-rsc-4/2urBcCl_ZhLaImCLF2IJgQREAAp3ZeETHI3byn6jACOvWxIB3Mbjtp63_Cqu9cgEACAP4WAmPHbhNgUazb01ODVyREpvQn_bA3YvIL0ptU6cDoc3IjlUVdH0i2eDknKiRGbsBIXPaVtZ9vf60866qqvqq2AYAkLPqLXYUGvElhKM0bMaTE5gmXb0NtUAtE5i?purpose=fullsize
 
https://images.openai.com/static-rsc-4/h6N5nZbN4LDTsXN4l3Aim2Kf0RFkrETUwZwpi7QIdYEu8tHisyVZ-Q6NfHm_j3eJ8AL6W7R-wKLn5Za1zS_xhRypE4cMzOuSPYEaieqEahWIlmZAOt0S1U8CSTxuEtp9CyjZznf3Gd4Pn1yJIg84wiLqgDPtHzR3hMPYB47omm9unD1sjCvgpGdibXewfPYO?purpose=fullsize
 
5

Why the Melting Trend Is Irregular

Two alkanes of similar molecular size can have noticeably different melting points because their molecules may pack differently in the solid state.

Some structures fit together more efficiently.

Better packing can produce stronger overall attractions within the solid.

Therefore:

melting point does not rise perfectly smoothly with carbon-chain length.

This is why boiling-point trends are often easier to predict than exact melting-point trends.


Physical State at Room Temperature

The changing intermolecular forces also affect whether an alkane is a gas, liquid, or solid at room temperature.

In general:

small alkanes → gases

medium-chain alkanes → liquids

large alkanes → solids or waxy materials

https://images.openai.com/static-rsc-4/2JuJI9t8atNho8jUh6JOFVA2FoXkMywiPHfqfAz914kD_1SSC15M3MujXj4Vxi8NFnV4RKN955kLkudrHeYzrjOTrMoyKFoEEcM57c5u8nHJeeuahJu7xsNKsh3D4vAIqZNnlkoIoJFetNW9KXS_ofEcKHaXxSy5iInM_OMmAWtUFRIjBnFrsToouC5KchJ6?purpose=fullsize
 
https://images.openai.com/static-rsc-4/iFJ_tlKnR6ZkGpPgCb4E7aZproMZuOheecwfs0TNoKIs6cUP-y8_RFqfUrV3HGWJ-eTW2zGxnCTXrWrM4WhuBGyQG5tXxJPtC0CXu0dSfyAmK25E6OFrwna7foY6-2PDJQgKOzdEfEWUT38zRcgmeYBkVkxc2zzzWzliRlzbexevmYcMUEJVNsd4JJJ6pgb7?purpose=fullsize
 
https://images.openai.com/static-rsc-4/NX-9VCZSLmag-D1vA06wYNqtfETssiNQi9M9moz9ARpPm2MEZm7qNstrVDX6rsRdS7KX6ArlPmktKV9eFe5OPEgE9TkL8DqbD14-N3C8sMQOWws5Ubk9HmfQ9u0BiFCROuE0ibMYbUG-ER1gBSqGY9BL7EGN2aisQvStiYWFVWQI1pUt-TcY_l4G8k17haP1?purpose=fullsize
 
4

At typical room conditions:

Methane, ethane, propane, and butane are gases.

Pentane and many intermediate alkanes are liquids.

Long-chain alkanes can be waxy solids.


Why Physical State Changes

Small alkane molecules have relatively weak intermolecular forces.

Therefore, relatively little energy is required to separate them.

This contributes to low boiling points.

As molecular size increases:

  • electron clouds become larger
  • polarizability increases
  • dispersion forces become stronger
  • boiling points increase

Eventually, molecules have sufficiently strong intermolecular attractions to remain liquid or solid at room temperature.


Volatility

Volatility describes how easily a substance vaporizes.

A highly volatile liquid evaporates readily.

Generally:

smaller alkanes are more volatile

and:

larger alkanes are less volatile

https://images.openai.com/static-rsc-4/a_yPzKLNND67mZtxx2OrbO5pfrucnmB-XzHi8vwmxl3hvHDWcplvyCDnCPsUa8njJNddMJUPy9Z7JhJKXeQHtm_d-ctndhnbA6pwQRl32SEs2v28ul4tBJkj9OZsfwCRt_Hl6q1pjvgeviHVsAO2CP4APObmjBMui9BXnw4G1SymvlpowC5tQhAE37_fDHTi?purpose=fullsize
 
https://images.openai.com/static-rsc-4/wCx6xKU_LopC76Ezi6B399k9jc2dNVACg2-as90xf1-mJeO6wV1kGu4jUCNuIb26L8z84BhwndBZebdBlHvVeE4B0a41qwNJVUXpotjx_WZ95Cx31Wa1cNrc-LfcZpiggT4REftfcCvd3hpYJNenMVQFLKGSB5GhyXoh6UfRJ5hMpoIXOQAqi5F7u37FAVF1?purpose=fullsize
 
https://images.openai.com/static-rsc-4/xcm7j10lQMQJ8RqKzUNX1cpu6rMT91QOlFHGeKylexF4CuBXVzPksXMOAZp6s0WbcXOwnmX7Y60uambU91-8IEmmEnopSyymOF3iF-BzBp8Gq-C8mvJurOR-g9CZf0oMmufljgHNzhdmDbq7nnT13A7gdWG97scwGp7w7sCSRkw4V2AezpbebaAGgXEOZQz_?purpose=fullsize
 
5

This is related to boiling point.

Lower boiling point usually means:

greater volatility

Higher boiling point usually means:

lower volatility


Volatility and Intermolecular Forces

Smaller molecules have weaker London dispersion forces.

Therefore, molecules can escape from the liquid more easily.

As alkane molecules become larger:

dispersion forces increase

so:

volatility generally decreases

This relationship is important when considering fuels and solvents.


Viscosity

Viscosity describes a fluid's resistance to flowing.

A low-viscosity liquid flows easily.

A high-viscosity liquid flows more slowly.

As alkane chain length increases:

viscosity generally increases.

https://images.openai.com/static-rsc-4/ghBSu1GES_jl5b_LurThEW19g-wRhyybZUfbyJgJjfkmtESsqWNvWul7mUd7TFVvraCfmnd_lbq56_YCP7pJvWyg2EjOZMTG8KDfBBgHuUcWqj9HPl2zeeNBSULT006tnjIo1RiOapvc3KjhPgLSG-NfTPHuYSVaP8ISXuoPyzXArEDP6-AcrxzQsG48lG6J?purpose=fullsize
 
https://images.openai.com/static-rsc-4/x36P_kQbyiuVSzBngGepHKdpNej2chAiYjiu61pvWGLJ3XkHfYal8xZ2xe7ptdVIzvqdSB0IvdP8hwG5gdOHRMcGTIuY2G7JE3Par5jfkmLePdVCKf7h27mlyPYsuyPO8B6ObhobGdZrYd23Bh2N4N7JFI8o2GRUQOpzmONTbsFtf0h9l304lO-Q1d7pcu8A?purpose=fullsize
 
https://images.openai.com/static-rsc-4/CEJezOhFgF7Cbnk8al8wJ0ghAiBevZZerMsu4dArkKL09zJCdalHlqhoMoRV712hFearojVrazf6u_pI2OeDT82S75NCoGDqF-Imf1sisRlULtpCer1eaXkN6HZvLqBAfQ3SI72WEthZGu0yLp4j0GasLxrdOuKtQDrYeM5_KmVmnccyeCy7W8TYiKUN1IBg?purpose=fullsize
 
6

Longer molecules experience stronger intermolecular attractions and can also interact and entangle more extensively.

Therefore, long-chain hydrocarbon liquids tend to flow less easily than short-chain hydrocarbons.


Density

Liquid alkanes generally have densities lower than water.

This means that many liquid hydrocarbons float on water.

For example, if a liquid alkane is mixed with water, two layers often form.

The hydrocarbon layer is commonly above the water layer.

https://images.openai.com/static-rsc-4/NtwAwPD_k9XlnjlDxFATpSD_c02yXb77iiN6gEHhouHx3DqLP7pXL1XYT3KLTHJBvU-zZiAaPq3CBluFh3-pSkLe8T5-GRnq1K6oL3tOkaHFPMGoJV_SSQekdDaVK1_PAe32TGtMk4A5Fm912qwwLK9l-7yX0L4xGqDZoIk3QItNqsAuouDV9CWVbghZkcjw?purpose=fullsize
 
https://images.openai.com/static-rsc-4/ZBkNKXIp9KRYh6Xb5icQnmroX_Y55CGhcBPinQvbbJYvfJCMJf6w3WnzxuzSV5S03VGEQ1wt0eLv1fFMHtlK7gQHPlxxp9GtpSS46CMzU_LImaaPudDusnOaph0K6v_uV3OMb7YbuRbiCC_8-mz4fG4Ofa0QmL_wKCHGUnCyTtZ_2l7oYE_9Z2CEm5gvvEKF?purpose=fullsize
 
https://images.openai.com/static-rsc-4/BDRp4oz9tFgtOC_QSktt4eECi_qPxRT9kEH_cxILXimacay1n3_z3g7AjyaTk8Uz7mFz94gQINjxk9cTyO0khBkY9ez3NgeiXVxavAgXKcCN8a43mHwiFLQ-dFiXgZcUUeUOSaQqLwdEjFxDWwS3GXN6y6YLi9PF-cFegrkT-zNXa3czzU_YpT_40qiUdyLw?purpose=fullsize
 
5

This behavior is caused by both:

  • poor solubility between the substances
  • differences in density

Solubility in Water

Alkanes are generally:

insoluble in water

because:

alkanes are nonpolar

while:

water is polar

Water molecules strongly attract one another through hydrogen bonding.

An alkane cannot provide similarly strong interactions with water.

Therefore, mixing is energetically unfavorable and the substances tend to separate.


Solubility in Nonpolar Solvents

Alkanes mix more readily with many other nonpolar substances.

This again reflects the general idea:

like dissolves like

https://images.openai.com/static-rsc-4/95MyKBeMgwS2di-fYt3EFxMa-yZZ4OE369jmPkFHAXmhtW_ZuRwrTHLhBMQlET3F3YHtkVv7g_6Ej94pkYOdzVHb2__2X5mi8HFbwFH5lPzW6v7OSPaVJYOY56Kx7xX6h6hQY5Qe2ka7y_vg8H81EIT2QuCUdaJSDCodMMJAp-6sTtIo4mEWT7-6VNcegJWk?purpose=fullsize
 
https://images.openai.com/static-rsc-4/cTywZ5rgEnMKExJzKJg2cWCuGg8DrWgyhTc9qPDofbe_lvK792-9nP8T79jBOCw-2OA3N4HWQxyTTh5_N3ctMgmbbUbI4okbfa2v-_NUWhI9z5x_eLzPZNLAhTN891a1SX9lCJUUYBDBYrDyOG3GQvi5PSriP1FpC4ID0-9nCGKKMFx0RU4KBJ7O_yPS5SrC?purpose=fullsize
 
https://images.openai.com/static-rsc-4/94i4Vot1mgb1ppBrjjG8cjgz0ZEXymCqTAFC1MrWUKUxIbbHZmypsJ-p48kIAdYyuFILD2YtfJ6SBNY91SIvzeNraFFMIi0ZeFiwKy6EaW7QLSxESZXRT6ZWqT0ijnkqUGl97dR-skBvLDzn7j_gJCr2z3YJAROxOXqHu6QuqSaYmzl_tNituziKswFMz2B0?purpose=fullsize
 
4

This property helps explain why hydrocarbons can dissolve certain oils, greases, and other nonpolar materials.


Electrical Conductivity

Alkanes are generally poor electrical conductors.

They do not contain:

  • freely moving ions
  • delocalized electrons that can move throughout the substance

Therefore, pure alkanes normally do not conduct electricity effectively.

This is different from metals and ionic solutions.


Colour and Odour

Pure lower alkanes are generally colourless.

Some pure alkanes have little or relatively mild odour, although hydrocarbon products may contain other substances that produce noticeable smells.

For example, fuel gases may have odorants deliberately added so that leaks can be detected.

The smell of a commercial fuel should therefore not automatically be assumed to be the smell of the pure alkane itself.


Summary of Major Trends

As the number of carbon atoms increases:

molecular size increases

number of electrons increases

London dispersion forces strengthen

boiling point increases

volatility decreases

viscosity generally increases

physical state tends to change from gas → liquid → solid

https://images.openai.com/static-rsc-4/ghBSu1GES_jl5b_LurThEW19g-wRhyybZUfbyJgJjfkmtESsqWNvWul7mUd7TFVvraCfmnd_lbq56_YCP7pJvWyg2EjOZMTG8KDfBBgHuUcWqj9HPl2zeeNBSULT006tnjIo1RiOapvc3KjhPgLSG-NfTPHuYSVaP8ISXuoPyzXArEDP6-AcrxzQsG48lG6J?purpose=fullsize
 
https://images.openai.com/static-rsc-4/a_yPzKLNND67mZtxx2OrbO5pfrucnmB-XzHi8vwmxl3hvHDWcplvyCDnCPsUa8njJNddMJUPy9Z7JhJKXeQHtm_d-ctndhnbA6pwQRl32SEs2v28ul4tBJkj9OZsfwCRt_Hl6q1pjvgeviHVsAO2CP4APObmjBMui9BXnw4G1SymvlpowC5tQhAE37_fDHTi?purpose=fullsize
 
https://images.openai.com/static-rsc-4/xcm7j10lQMQJ8RqKzUNX1cpu6rMT91QOlFHGeKylexF4CuBXVzPksXMOAZp6s0WbcXOwnmX7Y60uambU91-8IEmmEnopSyymOF3iF-BzBp8Gq-C8mvJurOR-g9CZf0oMmufljgHNzhdmDbq7nnT13A7gdWG97scwGp7w7sCSRkw4V2AezpbebaAGgXEOZQz_?purpose=fullsize
 
4

Melting point also increases overall, but the trend is less regular.


A Cause-and-Effect Chain

An important piece of chemical reasoning is:

Longer carbon chain

↓

Larger molecule and more electrons

↓

Greater polarizability

↓

Stronger London dispersion forces

↓

More energy required to separate molecules

↓

Higher boiling point

This reasoning is more useful than simply memorizing that boiling points increase.


Comparing Methane and Hexane

Methane:

CH₄

Hexane:

C₆H₁₄

Methane is much smaller and contains fewer electrons.

Therefore, methane has weaker dispersion forces.

Methane has a boiling point of approximately:

−162°C

Hexane boils at approximately:

69°C

At ordinary room conditions:

methane is a gas

while:

hexane is a liquid

The difference can be explained largely by the strength of their intermolecular forces.


Comparing Pentane and Octane

Pentane:

C₅H₁₂

Octane:

C₈H₁₈

Octane is larger.

Therefore:

  • octane has stronger London dispersion forces
  • octane has a higher boiling point
  • octane is less volatile
  • octane generally has greater viscosity
https://images.openai.com/static-rsc-4/3mrdtxbx9VHnz3Wh1MytpuvAh5RhQiKO498p05xrfdFug24AQKsXNs5YQR6sP0_S2HI8gsPrFp9SKhHNnWB6zSdwQ_sH0s2S6OI-BAz3VA7bYuGk9pSO7mghwzUbdM6telTzFuyd0k9ruFmpm4HM6KvUbGQNjb0Y_z2h0F6Jm9Ep2pVdgYepbgseY5SPYlbH?purpose=fullsize
 
https://images.openai.com/static-rsc-4/JicPl_bEljY6sqNgCAPVRu0ObH3Q9EbALhf9RfcgJuNF139r21E_LZ7nCKWJIg8KSDIxd0wrqoy3ldkDHG9P-63SA4liWUCNWlTRo7_khYKb_Jh-TsrtztnNlOdeQAn9LABI7Ex6Rz99-Ea8nxl_kFY_WKCgrUHRB3xhQns3-_TFNHn3InFtQ1XInGosEjYt?purpose=fullsize
 
https://images.openai.com/static-rsc-4/CUN_1tbASl0mlX40Xz77EE3DZS73_OHF-j3HGec-Do33ZdGpwrPxh-NRqFe4jXn10nVYRo6rL-1myO093-r1RK-xqElJmacT0_42MKLW_VJ5Lu2QnqLyCOu2_4Cxr9JQyYMMbb565NCnQQmwfEQ200jfec5saR1xBFSQ7umA8xHdPa1TeYFjTN4K8_-cDB8v?purpose=fullsize
 
5

Comparing Straight and Branched Alkanes

Suppose two alkane molecules have the same molecular formula.

The straight-chain molecule often has:

greater surface contact

with neighbouring molecules.

The branched molecule is often more compact.

Therefore, branching can reduce the strength of intermolecular attractions between molecules.

Result:

more highly branched isomer → generally lower boiling point

for comparable alkane isomers.


Practical Use: Gaseous Alkanes

Small alkanes have low boiling points and are gases under ordinary conditions.

Examples include:

methane

ethane

propane

butane

https://images.openai.com/static-rsc-4/oV44hFj5lNLYTeRrS-QJoimOGhhxfoVN37R9m_u2Af4Q4Rofju1p7WKP8dtK7p_LOfJnK717-ZEFA9Fzwe7jmiuDQctmKDL63jV114TY565Pxrs1Ew5Ap4qzN0Sw7vrZw5ZP-iyhvZ3vMN4f17uAa02KOBsWLMoHayCnTaT7AikjXtI548aETu2czmL_XiUH?purpose=fullsize
 
https://images.openai.com/static-rsc-4/oUpagQfBeOS12IOZtIhdqK1Nq9sKFnMcG3IqcakaD6FkvnL9jvwdHBER8U6ey8pP8k6MYqP810TVaMCHR7OOb9PZ0KrosBMfLbVaKKPtpUtmBPYTVv4wk9PtbPPFp4yDtMEZwuwSaPXftIEI8c48KN6TgTXkqJF4sD-iU_jaG6J8A-gQbQujcoEd3e_cuKF5?purpose=fullsize
 
https://images.openai.com/static-rsc-4/_QZe5q4_bbfRO6VmM4LE8Ayw7TMVoIWDijQNboqIW4Du0irKhynyTGL6EtCPsQ4zJi3K6FkK8vVz3svQ71hOi2l5lNzFoQ5y1zRf_aw1jWl_I_8EkkdLVox2Q63YmOl15Jg8D-vOhfL0356P3FPKvrFIxJclXig-od1UlY-jwtZNemF3r5GNecwfpuQ0H6BO?purpose=fullsize
 
5

Methane is widely used as a fuel.

Propane and butane can be liquefied under pressure, making them convenient to store and transport in suitable cylinders.

Their physical properties therefore contribute directly to their practical uses.


Practical Use: Liquid Hydrocarbons

Medium-sized alkanes are often liquids at ordinary temperatures.

Liquid hydrocarbons can be useful because they are:

  • relatively easy to transport
  • able to flow through pipes
  • able to be stored in tanks
  • useful as components of fuels
  • useful as nonpolar solvents in appropriate applications

Their boiling ranges and volatility strongly influence how they are used.


Practical Use: Fuels

Fuel must often vaporize or mix appropriately with air before efficient combustion can occur.

More volatile hydrocarbons vaporize more easily.

Less volatile hydrocarbons require higher temperatures to vaporize.

https://images.openai.com/static-rsc-4/hC69OL2SXdYSk0tJNJ_p4s15VoDIKh2bhX7bFeqY4OIuTH4SQwCGTwyZWCur808EiiXAOOiKWlBB10Zu0_lOWL0BzgJ2EO15DmpoBLBl_gG6mscsyTxj_OKentjYyAVHRuhk5Ou86jsBb3o-63ldpc5aL5pV7E_-qFN-KKd0l4CuvTaZmr_SbFjs9WpMIIU-?purpose=fullsize
 
https://images.openai.com/static-rsc-4/YiUqMNsvsQnTvM8FiZzBm2sKfUbxfM5X9mY2OECvLE0PJz_0KJ09MaeI9ML8it6UvmAhAUn2Hz72ONZlAtZqOwXV5BgpgATPQXJg0w0yxAr5s_h8_svcDmBf6Lg5ZUZ0ba3O7TxfJT3vQ0QpGIBjkm-uel_eJc3MevFJcYr67vDPt9Oh4mnhNEz3BImIH5EI?purpose=fullsize
 
https://images.openai.com/static-rsc-4/tGr2zkyvTOqttIi5TsjyCjjNynh2AiV8H0rI1pjcYMuLqgFZkmEjXFHdyUiNy62zUOTFzOOLDCF6iibvpxMiHarKrrdYg3Qy8jg8kag0mt0y9V5wJJV6qzmA0T9BxIoVzR75K32_cPWYJJLtUGxz7IVL8VmNAOtE-QwSRzWhZs-ichMyaUsgFnSRPrtB7frr?purpose=fullsize
 
5

This helps explain why different petroleum fractions are suitable for different types of fuel.


Practical Use: Lubricants

Longer-chain hydrocarbons tend to have:

higher viscosity

and:

lower volatility

These properties can make them useful as components of lubricating materials.

A lubricant needs to remain between moving surfaces rather than evaporating immediately.

Longer hydrocarbon molecules are therefore better suited to many lubrication applications than very small volatile hydrocarbons.


Practical Use: Paraffin Wax

Very long-chain alkanes can be solids at room temperature.

Mixtures of these hydrocarbons are found in materials such as:

paraffin wax

https://images.openai.com/static-rsc-4/HR7ASske2KZF-o5trHMVFYujjwVkLTU6AZDtVl4sWv_Q1RKtHldNir-dSn1JRhD7kN0yDJTa8BTS3Hus5qeHaRYS8HzNWHohy-OjpZzFjpqme2fl8kSIPpvNj0GWfNRqIRYudC2n57J-Ni0jRuUAHlQcvmEn_3mYUpgrZWNMo-1r5JSZrYRD-coCfyiqc42-?purpose=fullsize
 
https://images.openai.com/static-rsc-4/-UenDz9_7bVTW-jNcsM8LWWH4cb-DHlFiJ_2TKJh1Ov62fOTnaDUn2LmLB2hUWPc7_JLG4pXfCz9P5saWX_Y6OidfHcCTBAHYTiMspF1aM7hHn0iXgF378Ryb-SBKvhX5DeyR3EetKHE17FoWCo3ojseQhX5GQjgoJtEg--xTdKbZ-s-_9zfYbxP-4gBhV43?purpose=fullsize
 
https://images.openai.com/static-rsc-4/QfKkmpH64mfPGc89wSwcsn1nE5I1z9Ndw0m0fXSPy12dboYYFHAqdGSZ6_q3n9R8R3dXdsoR_9_Npd_D9GrT9LgjsxSQyss9FB7hmON-SlCDOlK6ATGe9MsmnZZSzZV5MtfCqEXWieSROopkI1z-IjXbq1Ye5-TxvWxikS_FwqTPTuIUR-uQMHD89THzMKja?purpose=fullsize
 
5

Paraffin wax is used in applications such as:

  • candles
  • coatings
  • waterproofing
  • polishes

Its solid or waxy nature results from stronger intermolecular attractions between its relatively large hydrocarbon molecules.


Petroleum and Alkane Properties

Crude oil contains a complex mixture of hydrocarbons.

These hydrocarbons have different boiling points.

This difference allows them to be separated into groups called fractions using fractional distillation.

https://images.openai.com/static-rsc-4/OflEvWTSU5GTVfjKmBmpxRlalcr74sVvSwkF2CcfsT9Gy92YholqSMDbWWIHDF1u1stDTf08l_L6pAR1o72pP_XolRZZ-GPbVeFixCYFIT5sY8-7F1skSZXeiy__J8DYAfxtZkQRPy-8eiM16kfWNdWqLjvEoXQwJ9KEbknSi_keuXJb3qVXW30F1_crQO1P?purpose=fullsize
 
https://images.openai.com/static-rsc-4/hC69OL2SXdYSk0tJNJ_p4s15VoDIKh2bhX7bFeqY4OIuTH4SQwCGTwyZWCur808EiiXAOOiKWlBB10Zu0_lOWL0BzgJ2EO15DmpoBLBl_gG6mscsyTxj_OKentjYyAVHRuhk5Ou86jsBb3o-63ldpc5aL5pV7E_-qFN-KKd0l4CuvTaZmr_SbFjs9WpMIIU-?purpose=fullsize
 
https://images.openai.com/static-rsc-4/jRPz2ZaeiwnKITAjblxflF7-lOCMBh-GoZZvhJh4eq1Rsyfan_mUxuHPrHUF8See-fz8q4J7AzAKuettOR2W9heOf0BYJQy-G5Eo7U4Jb9gssxZ77HzZHflafItSOOy6DBlU42Ql70MK-I73bWJzxEW5xIYySfpDW2VKCNZUjSNV5Oe1eGIk-5tTV69Q91oJ?purpose=fullsize
 
5

Shorter-chain hydrocarbons generally:

  • have lower boiling points
  • are more volatile
  • are less viscous

Longer-chain hydrocarbons generally:

  • have higher boiling points
  • are less volatile
  • are more viscous

These differences help determine how petroleum fractions are separated and used.


Intermolecular Forces vs Covalent Bonds

A common misunderstanding is that boiling breaks covalent bonds.

It does not.

Consider liquid hexane.

Within each molecule:

C–C and C–H covalent bonds remain intact.

During boiling:

intermolecular attractions between separate hexane molecules are overcome.

The molecules themselves remain hexane molecules.

https://images.openai.com/static-rsc-4/Mu-NxJJVXTwqoFOxzYY32DD8-_DQxMHkCTeNDMM3RqMUNC7gYqjwsiULQJUTFAgr3F9n3ben4Sz_uSI9lG08a-rPfFg9hizteImkglpVhUx_JLeXf4ChJA0xrMVuVODKn2JIKkk0vaXDEtruQ5EGBY2rMCiP9y9jNR7mAspXkW4oPSSzGfYXkcf4X439-TBX?purpose=fullsize
 
https://images.openai.com/static-rsc-4/NX-9VCZSLmag-D1vA06wYNqtfETssiNQi9M9moz9ARpPm2MEZm7qNstrVDX6rsRdS7KX6ArlPmktKV9eFe5OPEgE9TkL8DqbD14-N3C8sMQOWws5Ubk9HmfQ9u0BiFCROuE0ibMYbUG-ER1gBSqGY9BL7EGN2aisQvStiYWFVWQI1pUt-TcY_l4G8k17haP1?purpose=fullsize
 
https://images.openai.com/static-rsc-4/eJkUGJucPOIonLCPobM1Bs5mfu7CFPlA-ERO_Yg2HirQUFixTfyO5JPYxypJPm3kuj0I7cL5qtzWz98kuLsd3uT2zwnAZGT1QbWp-2uftBkji-j2XQmo8rerVhcR2RpKqvqVIvQZyW0Q0XaDzaX6FGZULwoE6Ai4q3GfM-z_d7Ggl5pF3lx4PkBaZnJJaEIh?purpose=fullsize
 
5

This distinction between intramolecular bonds and intermolecular forces is extremely important.


Intermolecular vs Intramolecular

Intramolecular means:

within a molecule

Examples in alkanes:

  • C–C covalent bonds
  • C–H covalent bonds

Intermolecular means:

between molecules

Example in alkanes:

  • London dispersion forces

Physical changes such as boiling mainly involve overcoming intermolecular forces.

Chemical reactions involve changes in chemical bonding.


Worked Example 1: Boiling Point

Which would probably have the higher boiling point?

C₄H₁₀

or:

C₈H₁₈

Answer:

C₈H₁₈

Reason:

It is larger, contains more electrons, and experiences stronger London dispersion forces.

Therefore, more energy is required to separate its molecules.


Worked Example 2: Volatility

Which is likely to be more volatile?

pentane

or:

decane

Answer:

pentane

Pentane is smaller and has weaker intermolecular attractions.

Its molecules escape into the gas phase more easily.


Worked Example 3: Water Solubility

Would hexane be expected to dissolve readily in water?

No.

Hexane is nonpolar.

Water is polar.

Therefore, hexane has very low solubility in water.


Worked Example 4: Physical State

Why is methane a gas while many larger alkanes are liquids?

Methane is a very small molecule with weak London dispersion forces.

Larger alkanes experience stronger intermolecular forces.

Therefore, more energy is required to separate larger alkane molecules.


Worked Example 5: Viscosity

Which would generally be more viscous?

hexane

or:

a much longer-chain alkane

Answer:

the longer-chain alkane

Longer molecules experience stronger intermolecular attractions and greater molecular interaction.


Worked Example 6: Branching

Two compounds have the molecular formula:

C₅H₁₂

One is straight-chain pentane.

The other is highly branched.

Which generally has the lower boiling point?

The more highly branched isomer.

Its compact shape generally reduces effective surface contact between molecules.


Worked Example 7: Boiling

What bonds are broken when liquid octane boils?

Under normal boiling:

the C–C and C–H covalent bonds are not broken.

Instead, intermolecular forces between octane molecules are overcome.


Worked Example 8: Predicting a Trend

Arrange these in order of increasing boiling point:

propane, hexane, nonane

Increasing molecular size:

propane < hexane < nonane

Therefore, expected boiling point order:

propane < hexane < nonane


Worked Example 9: Practical Application

Why are long-chain hydrocarbons more useful than methane as components of lubricants?

Long-chain hydrocarbons:

  • are less volatile
  • have higher boiling points
  • generally have higher viscosity

Methane is a gas under ordinary conditions and would not remain as a lubricating liquid between moving surfaces.


Worked Example 10: Explaining a Trend

A student states:

"Octane has a higher boiling point than butane because octane has stronger covalent bonds."

This explanation is incorrect.

The important difference is not that octane has fundamentally stronger C–C bonds.

Instead:

Octane is a larger molecule with more electrons.

Therefore, it experiences stronger London dispersion forces between molecules.

More energy is required to separate those molecules.

Therefore, octane has a higher boiling point.


Reading an Alkane Property Graph

A graph of boiling point against number of carbon atoms generally rises as the carbon number increases.

https://images.openai.com/static-rsc-4/4fT0EDaQI7bdJuUN_3czjb0LH7-M6fro1y0nXGNVSb8eiD78TTWl8nYf0eOk7Z3cdWqhS6eucKDKS9XW_-AEU05M6LDmmd_xbjaVwxr7cAN7M_rtg71yncNMJJYpbade5R_HCOdexa0DLfOTbcrjOgjiw6p1b3HwY0bBHN52LlhqRYqp4pnW3ProcxIamWkA?purpose=fullsize
 
https://images.openai.com/static-rsc-4/9o4cRF57w7FhDgNhwGeOamNGs1mWCkj-yFgVL5Z2S42at1bnkyouCKtRq9WYm8GnIlIl6JpSPAv5AuLxlh1ci6chnl0X7lpzqePiwgK8krMrDWYQ1mvfwnVM1bM73z9XnIwwech88AM2K9pfKJ1S8HkP3-iNM3dS0kPIvYjPVfuafwHWfPHMbg9ihNKi1myM?purpose=fullsize
 
https://images.openai.com/static-rsc-4/P0s2_feI9c4Mxhjkfxir1j_hDrGiDDqi7cjuei0QrDgP9ckDY_5qrT6LQ9R06tXYd1tOpW5cbTwZglzl8AIcVrz2Siiz6dlOV2Lkj9hcCf4i4RovXA0ndvnFJu3-BMF6UbJhK4rD9znrDKWnAr9heDqgGnLE3Vq7vlQGTc3onwbUgCIUWJpskzyU42gws0Cc?purpose=fullsize
 
5

When interpreting such a graph:

Step 1: Identify the variable on each axis.

Step 2: Look for the overall trend.

Step 3: Compare specific compounds.

Step 4: Describe the trend.

Step 5: Explain the trend using molecular structure and intermolecular forces.

A strong scientific explanation does more than say:

"Boiling point increases."

It explains why.


Explaining Trends Scientifically

A useful structure for an explanation is:

Observation → Molecular Change → Force Change → Property Change

For example:

Observation: Boiling point increases down the alkane series.

Molecular change: Molecules become larger and contain more electrons.

Force change: London dispersion forces become stronger.

Property change: More energy is required to separate the molecules.

Conclusion: Boiling point increases.

This reasoning can be used for many questions about alkane properties.


Practical Properties Summary

Smaller alkanes generally have:

  • lower boiling points
  • greater volatility
  • lower viscosity
  • weaker intermolecular attractions

Larger alkanes generally have:

  • higher boiling points
  • lower volatility
  • greater viscosity
  • stronger intermolecular attractions

All alkanes are generally:

  • nonpolar
  • poorly soluble in water
  • soluble in many nonpolar substances
  • poor electrical conductors

Common Mistakes

Mistake 1: Saying alkanes have no intermolecular forces

Alkanes experience:

London dispersion forces


Mistake 2: Confusing intermolecular forces with covalent bonds

Covalent bonds act:

within molecules

London dispersion forces act:

between molecules


Mistake 3: Saying covalent bonds break when an alkane boils

Boiling overcomes intermolecular forces.

The molecules themselves remain intact.


Mistake 4: Saying larger alkanes have lower boiling points

The general trend is:

larger alkane → higher boiling point


Mistake 5: Saying alkanes dissolve well in water

Alkanes are generally nonpolar, while water is polar.

They therefore have very low water solubility.


Mistake 6: Assuming melting points increase perfectly smoothly

Melting point is influenced by molecular packing and symmetry as well as intermolecular forces.

The trend is therefore less regular than the boiling-point trend.


Mistake 7: Assuming all alkanes are liquids

Small alkanes can be gases.

Intermediate alkanes are often liquids.

Long-chain alkanes can be solids.


Mistake 8: Saying branching changes the molecular formula

Structural isomers can have the same molecular formula but different arrangements of atoms.

Branching can change physical properties without changing the molecular formula.


Did You Know?

The physical properties of hydrocarbons are one reason crude oil can be separated into useful fractions.

https://images.openai.com/static-rsc-4/8B02yMHo2Mx8QyjeTFQERa3r-tvTilp_6JZjf1bMMp_kLGHHLUulZcM1tydGk-fOam76HV2tOhQ4gNf0FvK77YrtW46wrHTKoqFuDKPizBhp3ADUqVqV3wvsMG7uvJqCqQ-hy5_mrNUf0cv5X_9N2fV3_wKvHDT7X8eXPit68jMf7Ncw0LkXSz20FmiqmZiL?purpose=fullsize
 
https://images.openai.com/static-rsc-4/ghBSu1GES_jl5b_LurThEW19g-wRhyybZUfbyJgJjfkmtESsqWNvWul7mUd7TFVvraCfmnd_lbq56_YCP7pJvWyg2EjOZMTG8KDfBBgHuUcWqj9HPl2zeeNBSULT006tnjIo1RiOapvc3KjhPgLSG-NfTPHuYSVaP8ISXuoPyzXArEDP6-AcrxzQsG48lG6J?purpose=fullsize
 
https://images.openai.com/static-rsc-4/hC69OL2SXdYSk0tJNJ_p4s15VoDIKh2bhX7bFeqY4OIuTH4SQwCGTwyZWCur808EiiXAOOiKWlBB10Zu0_lOWL0BzgJ2EO15DmpoBLBl_gG6mscsyTxj_OKentjYyAVHRuhk5Ou86jsBb3o-63ldpc5aL5pV7E_-qFN-KKd0l4CuvTaZmr_SbFjs9WpMIIU-?purpose=fullsize
 
5

Hydrocarbon molecules with different sizes have different boiling points.

These differences allow petroleum refineries to separate complex mixtures into fractions used for:

  • fuels
  • solvents
  • lubricants
  • waxes
  • chemical feedstocks

A change at the molecular level — such as increasing carbon-chain length — can therefore have major practical consequences.


Key Terms

  • Physical property: Characteristic that can be observed or measured without changing a substance into a different substance.
  • Nonpolar: Having little or no permanent separation of electrical charge across a molecule.
  • Intermolecular force: Attraction acting between separate molecules.
  • London dispersion force: Intermolecular attraction caused by temporary fluctuations in electron distribution.
  • Instantaneous dipole: Temporary uneven distribution of charge in a particle.
  • Induced dipole: Temporary dipole produced by the influence of a nearby charge distribution.
  • Polarizability: Ease with which an electron cloud can be distorted.
  • Boiling point: Temperature at which a liquid boils at a specified pressure.
  • Melting point: Temperature at which a solid becomes a liquid at a specified pressure.
  • Volatility: Tendency of a substance to vaporize.
  • Viscosity: Resistance of a fluid to flowing.
  • Solubility: Amount or ability of a substance to dissolve in another substance.
  • Density: Mass per unit volume.
  • Intramolecular: Acting within a molecule.
  • Homologous series: Family of related organic compounds with similar chemical properties and a common general formula.
  • Structural isomer: Compound with the same molecular formula as another compound but a different arrangement of atoms.

Key Trends

As alkane carbon-chain length increases:

Molecular size ↑

Number of electrons ↑

Polarizability ↑

London dispersion forces ↑

Boiling point ↑

Volatility ↓

Viscosity generally ↑

Physical state tends toward gas → liquid → solid

Melting point:

generally increases overall, but irregularly

Water solubility:

remains very low


Key Takeaways

  • Alkanes are generally nonpolar molecules.
  • Their main intermolecular attractions are London dispersion forces.
  • London dispersion forces arise from temporary changes in electron distribution.
  • Larger alkane molecules have more electrons and more polarizable electron clouds.
  • London dispersion forces generally become stronger as alkane molecules become larger.
  • Stronger intermolecular forces require more energy to overcome.
  • Therefore, boiling points generally increase as carbon-chain length increases.
  • Melting points increase overall but show a less regular pattern because molecular packing is important.
  • Smaller alkanes tend to be gases, intermediate alkanes liquids, and sufficiently long-chain alkanes solids or waxy materials at room temperature.
  • Volatility generally decreases as chain length increases.
  • Viscosity generally increases as chain length increases.
  • Alkanes are generally insoluble in water because alkanes are nonpolar while water is polar.
  • Many liquid alkanes are less dense than water and form a separate layer above it.
  • Branching generally lowers boiling point among comparable alkane isomers because compact molecules tend to have less effective intermolecular contact.
  • Boiling does not break the covalent bonds inside alkane molecules; it overcomes intermolecular forces between molecules.
  • Alkane physical properties help determine their practical uses as gases, liquid fuels, solvents, lubricants, and waxes.
  • Understanding intermolecular forces allows us to explain and predict the physical properties of members of the alkane homologous series.

4. Combustion Reactions

Learning outcomes
  • I can describe combustion as a reaction between a fuel and oxygen.
  • I can distinguish between complete and incomplete combustion.
  • I can write and balance combustion equations for simple alkanes.
  • I can identify the products of complete and incomplete combustion.
  • I can explain the environmental impacts of combustion reactions.

https://images.openai.com/static-rsc-4/H9flQaZNuUJN0dxeRH8Vl7owO1OU5dTrezu4eLDQHzJOufDmwcanfp0TA23_EU5-C6u5X0ywbcU6RhKUB5MhgewgvZ00tlVsZ5DJb3XjbtHKlnak8UUX1WDT4q8mtZwJcXw3lQl_s7T0mKriccGlqo5CwB6DAzxXxrKC3UZS2Zn9YzbAzDcmzOja7VQ55e7X?purpose=fullsize
 
https://images.openai.com/static-rsc-4/gVPOZLNjk_DCMPbc0y9ymWPmXh4MtCesvXP5xyOzxx3SJ0FrzrZxn4Fwn7dgMkuPtxdxs7UUNXgG0Df8Rno8poHtZjvqyL2lk78q4jSuUjfSYgtYwsK0xFycfO66xSDhvfEUHsJqTlFafITjRYdrXVqt5Xrd2zuSdG1tteXGKYNA_suKmMQX_LOITZvWcESi?purpose=fullsize
 
https://images.openai.com/static-rsc-4/8daVe-54Mjii2C0XN2ULytZIdcP0xhbrbV5PXzEYoMKBMOt9S93aqQHFv_EglTSqbHVi_SUVEMoPJB5nU8bjDT8THXcfC1dr2_2_fojz8bVaMKBJdL1301a53wgDnzALPORTuYRd3yqjVN-NTQA5oV57kiiTynAEQ66it2z-KP0RACE1DL0ehfGPYRBJX0XC?purpose=fullsize
 
6

What Is Combustion?

Combustion is a chemical reaction in which a substance reacts with oxygen and releases energy.

The substance being burned is called the fuel.

In a combustion reaction:

fuel + oxygen → products + energy

Energy is usually transferred to the surroundings as:

  • heat
  • light

Because combustion releases energy, it is an exothermic reaction.

Combustion reactions are important in transportation, electricity generation, heating, cooking, industry, and many other areas of everyday life.


Fuels

A fuel is a substance that can release useful energy when it undergoes a chemical reaction.

Common fuels include:

  • methane
  • propane
  • butane
  • gasoline
  • kerosene
  • diesel
  • coal
  • biomass
https://images.openai.com/static-rsc-4/0aJ9Mv5wT8PMxeULwbRiHoGa7OhJOrW84GYmOKzidNpCCB9xBz766bTPDCYJhiE3fgB9yKli_6EgG4aXBp3auBMKfld0Tmt6Sz-qC04LJ5a9Kf9XKlIJ9sVVhP0DJVToJyOXF3TGFDrEcoJ8chKccDGNlbydVSXuEWjyj_WUgyuORp2uvprjjkTMyVNF71-x?purpose=fullsize
 
https://images.openai.com/static-rsc-4/vvzzizeFpLUQt0BE1exD-S6x7a-Ab-2L5FQs-cQGRnYW9r4XbsNmuF1QZq6ef9yY_ZvqTpSlv2iPtCJpL2LGMbhsQ-HuBdkt3rfhFwAeXNNfhoYTxF9XBYzVhaB8oQghzhQwCSvA2vSvR_-cvAlhqkfTG4MRZ2Fyx1YeVyRuEbx7GB_pZFTNbV7NhwxcpidL?purpose=fullsize
 
https://images.openai.com/static-rsc-4/RmdCm_fi6JqR_NN4QoUtfjH24ekSk0TCOUIVaOJe5KjLvtBotjsP3rv2hhtzZSm-o4jW9QDUuzZN-7hgMK1EVcUoX23oQA0X8cbjEQ1RlvEZPYAiDyoa4QNsWzN4L1aPoilXfFo8ztc_loH-BYZroWO5rx9QFTyKncDu769P223kkvNMF0IlxhblxdKnfzuB?purpose=fullsize
 
6

Many common fuels contain hydrocarbons.

A hydrocarbon contains only:

carbon and hydrogen

Alkanes are an important family of hydrocarbon fuels.


Why Alkanes Burn

Alkanes react with oxygen when sufficient activation energy is supplied.

A flame or spark can provide the initial energy needed to start the reaction.

During combustion:

  • bonds in the fuel are broken
  • bonds in oxygen molecules are broken
  • new bonds form in the products

Overall, forming the new bonds releases more energy than is required to break the original bonds.

Therefore:

energy is released overall

and the reaction is:

exothermic


Complete Combustion

Complete combustion occurs when a fuel burns with a sufficient supply of oxygen.

When a hydrocarbon undergoes complete combustion, the products are:

carbon dioxide + water

Therefore:

hydrocarbon + oxygen → carbon dioxide + water

https://images.openai.com/static-rsc-4/9AsER8qqf01xjl_rpR1yiTu1T0X2KDDzFN_xHCn_CAmJN0wGp-0aWU4n3kD1Genm3SiNrVUK_bCLNrWq_e8M4eubZkz2jg-FU1h6-KfNQR4vQTdD8s0nneSz9g6cOJew9XuEg3BTS1hz8DKj8oP6QTZOZLQs3b40_FtgVJfdRGFa9ng5HAp3xI1ZBLUtwDQs?purpose=fullsize
 
https://images.openai.com/static-rsc-4/U03bJCIpiCN1yujeWlLMXFxRS-ZVX-aI6sX33ad4ytMtYs8KY5M-aj4lXsyiRRYKRFQRr2I_KAhPdluA45fjLP-_GCG6suQVbmts9hetfTqZSGF20-4MVWgGs_uRxkFgSqBozQCjbRW2Vt4H3JvAQyx6Y_G8ajL1Tfj3Ms_xBNdbvIJKPjjv0SyXURkiLnVc?purpose=fullsize
 
https://images.openai.com/static-rsc-4/d6r2JvXyuZiH9ws3wb1Z0EOudOr006THyoZWvmdyAGRLu0rmhBuGQkAGZBW9hYmSbg3fYzLd84LgRpcGQHCbC6jdZf9MkA5Kgzxwqk5qTIRoO0pvhuzwbBNfTohngW09LPd5y8KP1__c3Vw6-6kbNhKOPeq6K9l_zonpRXiBPJKee8oKtjon8omri9Rzqady?purpose=fullsize
 
5

For an alkane:

alkane + O₂ → CO₂ + H₂O


Complete Combustion of Methane

Methane has the formula:

CH₄

The balanced equation for complete combustion is:

CH₄ + 2O₂ → CO₂ + 2H₂O

Check the atoms.

Left:

C = 1

H = 4

O = 4

Right:

C = 1

H = 4

O = 4

The equation is balanced.


What Happens to the Atoms?

During combustion, atoms are rearranged.

They are not created or destroyed.

In methane combustion:

Carbon from methane becomes part of:

CO₂

Hydrogen from methane becomes part of:

H₂O

Oxygen from the air becomes part of both products.

https://images.openai.com/static-rsc-4/7Cpd8GTe7dU2f6Y6Rsx0nco8x6Z0xyrc-DXacQOwSJNjVvEqzHiGOqKDnFzetC3OEd0_RnC4XZXexDcKI5N5EUcaM620605JuO6rO_P3l1WabdGwZajP-zFuXpOKm8IPHD_CNSPE8ltvtid5dluQ-PpCdY_odjwbtD1KBYKlAZWqJ8iXYNIauUEyl2Nz8eZN?purpose=fullsize
 
https://images.openai.com/static-rsc-4/T3CkPd98ytCuPrwXZnpLw2AwKJcNJ7V5m0QUgUceNRXaTxItaW9KZCK9dDiTDm9DBytVhLz7wicEIDCy0RrvKWgxuGpgUq-Kj2_-mEWLRfHOJBo8JI3CaT7MV3EaSmF6wnaycPAh0B-1HSvWZWG1XxfIkjFS_gEDFSNyVj2jMHXo7kaBAHssGuCdfca1z32e?purpose=fullsize
 
https://images.openai.com/static-rsc-4/msD3NzchL4kdW_uXfr3rcRUZUQ_GP7JbplNrgAdVMCDBaVOsxamGsQa1ZTPhBGCm7AojEVQJR-sebZsz1zrGUio8M0sfXHelW5t_ftSrNiXVNflcH1WRSbMeZU6_ocxTe0c-pHy3beFLwXutVu5jAvO50RW1XxN1efP4q1fLwuWtWn6hrMEpSuqFYHsqTKhr?purpose=fullsize
 

This demonstrates the law of conservation of mass.


Balancing Combustion Equations

A chemical equation must contain the same number of each type of atom on both sides.

A useful order for balancing alkane combustion equations is:

1. Balance carbon.

2. Balance hydrogen.

3. Balance oxygen last.

This method works well because oxygen appears in both products.


Example: Combustion of Ethane

Start with:

C₂H₆ + O₂ → CO₂ + H₂O

Step 1: Balance carbon

There are 2 carbon atoms.

C₂H₆ + O₂ → 2CO₂ + H₂O

Step 2: Balance hydrogen

There are 6 hydrogen atoms.

We need:

3H₂O

So:

C₂H₆ + O₂ → 2CO₂ + 3H₂O

Step 3: Balance oxygen

Right side:

2CO₂ = 4 O atoms

3H₂O = 3 O atoms

Total:

7 O atoms

This requires:

7/2 O₂

So:

C₂H₆ + 7/2O₂ → 2CO₂ + 3H₂O

Multiply the entire equation by 2:

2C₂H₆ + 7O₂ → 4CO₂ + 6H₂O

https://images.openai.com/static-rsc-4/OasTlWQpvX1JAVLndnJvAAlMa-G_UGwImQEqhxoX05DwvJQcxgzU1Q0ILiL6YDSNOGe08ycyBVkUni7YLFewH_NcwZCd_NnU5qDW_9Fs3Qeuf-mQkUFfBwbk_Vw35tJmNeRu43GJhh5QP9tgrfasromAthpPGf4ahCEuuMw3ikP5D8ohCbi8TMpkaF2ehY5z?purpose=fullsize
 
https://images.openai.com/static-rsc-4/xVdm2wNz_0w6Rl3yi-u3OA8XEUyTPZe5w5qu3vou4jdQ8KuxHvBOiS04-8FhL1_fMR-ha193PtYXYTiinZ--uCBRMkiEeZq78CnVz5afrZLyWcaisFBjbkZ5jlabjonAf0_GMGrnivgNUPATGC5sHy6uosq4lcjZ1frVEa18_HRmwVZg1smdQDz2VOvIDvss?purpose=fullsize
 
https://images.openai.com/static-rsc-4/u9s13PAaPuULWzEvQwtInZGJR1uyDU9_LWqOMbCbh0AMeVAKH2xiDqgowIQ8sfH3Ayo09iPauNhwu3atpBCAsk0uM5rpNzHu25Xgup9ZHvQw8oIA52J00a7o4OBp9wayONwnqgiPb8U-UsIimKglaytjDf2ECGss-d5njRZTGWWy_FMT75LQtbqUynmJaC23?purpose=fullsize
 

Example: Combustion of Propane

Start:

C₃H₈ + O₂ → CO₂ + H₂O

Balance carbon:

C₃H₈ + O₂ → 3CO₂ + H₂O

Balance hydrogen:

C₃H₈ + O₂ → 3CO₂ + 4H₂O

Count oxygen on the right:

3CO₂ gives:

6 O atoms

4H₂O gives:

4 O atoms

Total:

10 O atoms

Therefore we need:

5O₂

Balanced equation:

C₃H₈ + 5O₂ → 3CO₂ + 4H₂O


Example: Combustion of Butane

Start:

C₄H₁₀ + O₂ → CO₂ + H₂O

Balance carbon:

C₄H₁₀ + O₂ → 4CO₂ + H₂O

Balance hydrogen:

C₄H₁₀ + O₂ → 4CO₂ + 5H₂O

Oxygen atoms required:

From CO₂:

4 × 2 = 8

From H₂O:

5 × 1 = 5

Total:

13 oxygen atoms

So:

C₄H₁₀ + 13/2O₂ → 4CO₂ + 5H₂O

Multiply everything by 2:

2C₄H₁₀ + 13O₂ → 8CO₂ + 10H₂O

https://images.openai.com/static-rsc-4/Lz94uGAkVRi17b4ver2sSf601YrqRs54EuRR4QqjEePSXHv42Aas9wTy22MPAhKV1CBnFSTSs1Ut7arsCp3uD9PrOwSY5YgTmIG3YtOuD1Cku6NixFBrNpq9HZwnBM9mjulLvYzyOrC4jQIrnJBOJofeO-7pQ6PEZPLSbjZKdD3F53wHtfhVN2OicV4CIhVE?purpose=fullsize
 
https://images.openai.com/static-rsc-4/W3Tb14oW74oHBSfCHABR0SkJEQilx1pqt62vLMoe5Tm17LsoOykKuIy4kAfBvDIDlpEBLeznSG5n7Gnewniz3BHDZA08-LIVRmrHNFL0-Gyw8vu0mP6SrIdj6BsEHkj5VScYXVq-4IFBxuSFTuKwJ_wFDlkpFC0UV66973aJTy2wGIrRwnsRPQLht_qTmBIq?purpose=fullsize
 
https://images.openai.com/static-rsc-4/T7_6XnAFNaAjfMBv7Uv13aTlSqzVBfl-x0QW5bEOMpuIM-ocpym6_x5pV4-zwt1zdutkNOGEdICrittjlUlwB71jbwegghIIGO5tfZIoaQY4R_dT0zDdhse_0QGi2RMplOFxHNVmkoIbovhyu9F0G5jGHOj3yrT7xdGVcoB5kF-Kq73ZWY-SfStLdO35tzn9?purpose=fullsize
 
5

General Complete Combustion Pattern

For an alkane:

CₙH₂ₙ₊₂

complete combustion produces:

CO₂

and:

H₂O

The general pattern can be written as:

CₙH₂ₙ₊₂ + (3n + 1)/2 O₂ → nCO₂ + (n + 1)H₂O

For many introductory problems, however, it is usually easier and safer to balance each equation using:

carbon → hydrogen → oxygen


Complete Combustion and Flames

Complete combustion is associated with efficient burning when sufficient oxygen is available.

For many gaseous hydrocarbon burners, a well-adjusted flame with good oxygen mixing is often:

blue

https://images.openai.com/static-rsc-4/N8BnqPHnzRZZFPYyP_XLrU2cAVlFOb92cnHDUEo6BPGknogNlHE_t0huITC0xOhwyl4-9Kz0_wDZcEKVR3H_R4NuKGNixcf0L0YuCdvzB2SajGA5q_TPngcfG9d0v69ulbmNtXEFMiwH0S_hiBggnYg9H_zD7NZgAqavn3Qd30mnWO3V_5vKFex-rcHhbp7I?purpose=fullsize
 
https://images.openai.com/static-rsc-4/V6beFGhnkaFs-fwQU6EbBk3cnlFl6bLFs9SqdMO0bsDbEJE_ZsMKSE6hkZHwpLQ0IoSbAswPa7NId31qrPNrwNj8deZCKtE5Jv77ttiN0o425y-HJdKn9iIYNnJ8EMeyZRieqYg_fEnleRw9c9aQx77qyMKtqewR0L6qAJzQAJ22bHqucs2maXRwJTKMJOAT?purpose=fullsize
 
https://images.openai.com/static-rsc-4/n8uSbAEXGYn0m5rrDUOHlj_V5i6OAN8wegDv5soNNwfnFVtI2kkQqPNmXqNgPpYuHD1dTud5QCYHKKopZPcUFji6jXmog05qpDZ5_9rnA3L-GcBo0WGAQK0mItK0AJxc66o9443jgbaKun2-mKvVFwLxd2E20aOFn9HTLdL6ih83w4ubblB81Ly7R91BzzSN?purpose=fullsize
 
5

A blue Bunsen burner flame, for example, usually indicates relatively complete combustion.

However, flame appearance depends on the fuel and burner conditions, so colour alone should not be treated as a universal test for every combustion system.


Incomplete Combustion

Incomplete combustion occurs when there is not enough oxygen for the fuel to burn completely.

Instead of all carbon atoms becoming carbon dioxide, some may form:

carbon monoxide (CO)

or:

carbon (C)

Water is still produced from the hydrogen in the hydrocarbon.

Therefore, possible products include:

carbon monoxide + water

and/or:

carbon + water

Some carbon dioxide may also form.

https://images.openai.com/static-rsc-4/gVPOZLNjk_DCMPbc0y9ymWPmXh4MtCesvXP5xyOzxx3SJ0FrzrZxn4Fwn7dgMkuPtxdxs7UUNXgG0Df8Rno8poHtZjvqyL2lk78q4jSuUjfSYgtYwsK0xFycfO66xSDhvfEUHsJqTlFafITjRYdrXVqt5Xrd2zuSdG1tteXGKYNA_suKmMQX_LOITZvWcESi?purpose=fullsize
 
https://images.openai.com/static-rsc-4/DynJZMDgMmF5Uhj8oIPAZmQrfWase45EtsBE1PR9E8XqBw0Q7Ztig5AH5QktPX3CRskqRyAioJ32kYPpe6d-FuTLD3_XSjPkAa8bnF92IWdWfSPqprcuFpd5vFzdNMfnqchEPxXmud3kN_WjAVDXYr1Za_lmpP0IKoHmulk7r-o6tHGWBT2IZrD3AANPoC52?purpose=fullsize
 
https://images.openai.com/static-rsc-4/d6r2JvXyuZiH9ws3wb1Z0EOudOr006THyoZWvmdyAGRLu0rmhBuGQkAGZBW9hYmSbg3fYzLd84LgRpcGQHCbC6jdZf9MkA5Kgzxwqk5qTIRoO0pvhuzwbBNfTohngW09LPd5y8KP1__c3Vw6-6kbNhKOPeq6K9l_zonpRXiBPJKee8oKtjon8omri9Rzqady?purpose=fullsize
 
5

Real incomplete combustion can produce a mixture of products rather than only one carbon-containing product.


Why Incomplete Combustion Happens

Incomplete combustion can occur when:

  • oxygen supply is limited
  • air and fuel do not mix properly
  • a burner is poorly adjusted
  • combustion occurs in a poorly ventilated space
  • combustion conditions do not allow the fuel to burn completely

Less complete oxidation of the carbon occurs.


Incomplete Combustion Producing Carbon Monoxide

Methane can undergo incomplete combustion to produce carbon monoxide.

One balanced equation is:

2CH₄ + 3O₂ → 2CO + 4H₂O

Check:

Left:

C = 2

H = 8

O = 6

Right:

C = 2

H = 8

O = 6

The equation is balanced.


Incomplete Combustion Producing Carbon

With even more limited oxygen, solid carbon may form.

For methane:

CH₄ + O₂ → C + 2H₂O

This carbon can appear as:

soot

https://images.openai.com/static-rsc-4/MZOl1mjaimwAeUheFAdUInCwlo0_hBwukfzvbYHl1-yqpz3qZCTol4DrXVe2lqh7kynhXuHr5dKbcjHUY5W73o_lsQprWzkvlPyY7kilREQrCxpcVikv7Sb1hwEKA6Ot7IMP4jW6ZvacEjCPrEw7z2-xbrUHd08SqGgHVp2Ehl25RYgwhXKt0tl5UyiJ1HAQ?purpose=fullsize
 
https://images.openai.com/static-rsc-4/z5Yu5wl5wQR6fNZxVlpxKKWSwb7naU9vjcKzEEq4MQEDTsltAmVKtrCX35NrLmOoowMeYiU-dkA9DR9f5-Nlxcu7AFmS57EOsruCe2Fq1zHxq_tCwVVVbxScDZPuCdXWA-AdOlcWH3ger1VQQRinNdJMpIX4r-X-ugFZbKUDLoxuRU1h9-TNd1bRAo2p7pCl?purpose=fullsize
 
https://images.openai.com/static-rsc-4/tfnldxJ9r4OGlzbywFK69tcashmmBfX3MbCEBW0bKrIsyT1moBhPnUb-7Lauz1JoR5StaUsA3s_NImKdJT5M0PEclSD5ULBwfDVUnsk7uanSqFNOHkTV7PpTqVyMPPur8Cq65hulgcRcp2ZaCLnBVw8ZTMG4ZBjEoOzEXepPCawMCiWYXrqW6fcX0fseOkua?purpose=fullsize
 
5

Soot is evidence that carbon-containing fuel has not been completely oxidized.


Complete vs Incomplete Combustion

Feature Complete Combustion Incomplete Combustion
Oxygen supply Sufficient Insufficient
Main carbon product CO₂ CO and/or C, often with some CO₂
Hydrogen product H₂O H₂O
Energy released More efficient energy release Less energy released from the fuel
Soot Little under ideal conditions May be produced
Carbon monoxide Minimal under ideal conditions May be produced

Carbon Monoxide

Carbon monoxide, CO, is a colourless and odourless gas.

It is dangerous because it interferes with the blood's ability to transport oxygen.

https://images.openai.com/static-rsc-4/FHeYYbW1Yka-SX2mdzHuqlrA4VvlEsZd4aG_j8qRVdb_Xhpsm76001yPFRTxAyg7RuDJIptR6VOHeUMpC0nGQPVTOPK2g0t4c7Gd7qH3LbRsel2OH411O48Y5kV9IClGZcueKLlBvf-3wdSSJ_Bp4fCs6DnkmrukOrrmJFfT1aKFTK1Ie6DeuhdfaW62fPJg?purpose=fullsize
 
https://images.openai.com/static-rsc-4/sVGRmg7ql7gEWGJ1yAn0Chm0otNhnO4YOgFOTmT3ilofHehXasOZzNbLZaqqqCSrp9mubyJ4mrxN4CR4g5SivR0A7U2nD3sLDOi6wmpjdsgQCWMk8M_FcealB2GM4isSX_e51wbYnm1BIUdSwdUA05MLw16o9PGjesmcqenY5n_JTic76u8LU0iLmD_0hbj7?purpose=fullsize
 
https://images.openai.com/static-rsc-4/DWCCyUvjI4qixBsoX6ub4typePQNgcvpNpy4q5qRD4stAf-9IzAMHskcTkmaqJ0E4O_fx-UO2Ahgh4aKFc2bKVIscF7xWizYIxVxl5tpIX9C5pS0bb6HCImHddosGwTqObWq1_IebeU09RpYZfQgKsy3e8kameVVYkYjeH4xaDhhZ3n2hORBlUpBHDLezWzi?purpose=fullsize
 
6

Carbon monoxide can be produced by incomplete combustion in equipment such as:

  • faulty heaters
  • poorly maintained furnaces
  • engines
  • generators
  • poorly ventilated combustion appliances

This is why proper ventilation and correctly maintained combustion equipment are important.


Why Carbon Monoxide Is Dangerous

Red blood cells contain hemoglobin, which normally transports oxygen.

Carbon monoxide binds strongly to hemoglobin.

This reduces the amount of oxygen that the blood can transport effectively.

Because carbon monoxide has no colour or smell, people may not notice its presence without appropriate detection equipment.


Soot

Soot consists largely of tiny carbon-rich particles formed during incomplete combustion.

It can:

  • blacken surfaces
  • reduce air quality
  • enter the respiratory system
  • contribute to atmospheric particulate pollution
https://images.openai.com/static-rsc-4/T3JtrpMVKXWNArSDWDZUBrrXrN48hTNltSoSfWk4MyGn7lJJJnXHvquWMtDRZui2tamn6kiQpRo1QKEIUFdZfzPs1Hr5DBKCivslgZOb3rfRm2Qm_vO-QSx-PtSOP_GxHzwIh_kIygcr1kRS3yIn_uk4VA3Dkkbuz_PY_X4PxuHQA2DLMKh3unnJ10_XjL7h?purpose=fullsize
 
https://images.openai.com/static-rsc-4/8QkQbyXs5SCEPPcShyflxRrijv-AMWowGEB2mupQEBEugxjnt5csbq0k5ErabNVwAU4DwFJvfzN37mIoor68o9HauHFDh5ZafinpoUEcDnY1Vzj7ctRazrAHFsphodQ1ysHPlAYflMfwkiKFs_oAQ0XJGRh75wlCX5JJo_KziwiwLX8BGi5NTafr-5LSeV2V?purpose=fullsize
 
https://images.openai.com/static-rsc-4/4Fyz7HJLxw5ZxmW2cGmpwJiLHtRZHKwLKvZjNc0KNeF2XTmKFKNc1jCQwXdycIo6AwQmNKMZIJL7pIXeqi4UvW4IOyx09uZrb2OtkhOxzDDmggSkiSTqHd9AXwgdchlzCHKJZHmftLo7GB2--eHXv2tGL35VBNR7bne7DLOIPcIpaVm7g0YD98zUwRPu4dzk?purpose=fullsize
 
5

Black carbon particles can also absorb sunlight and contribute to atmospheric warming.


Energy from Combustion

Combustion reactions are exothermic.

Energy is released because the products are at a lower chemical energy than the reactants.

This released energy can be used for:

  • heating
  • cooking
  • transportation
  • generating electricity
  • industrial processes

Complete Combustion Releases More Useful Energy

Incomplete combustion does not fully oxidize the carbon in the fuel.

Products such as:

CO

and:

C

can still undergo further oxidation.

Therefore, incomplete combustion generally releases less energy from a given amount of fuel than complete combustion.

This makes incomplete combustion:

less efficient

as a way of obtaining energy from the fuel.


Carbon Dioxide and the Environment

Complete combustion of hydrocarbon fuels produces:

carbon dioxide, CO₂

Carbon dioxide is a greenhouse gas.

https://images.openai.com/static-rsc-4/9-x-iDHwy_K0hgOOrWHC9laYHcxGjaXwIRy5-Pmkx2rFbFAaJnUjHn_DNq8CTEgI4QmKATWsxaif_WIPpG32wdYSf0z7g-o9vPEf47pugDbcYZY8xOpm0nfq0aAXN5N8HS81yn04dfk0tU9EeKWzojR4Dp8Uzyi1wCmjHKY422XTm4eYKrK7V_XONUrE0XVK?purpose=fullsize
 
https://images.openai.com/static-rsc-4/RmdCm_fi6JqR_NN4QoUtfjH24ekSk0TCOUIVaOJe5KjLvtBotjsP3rv2hhtzZSm-o4jW9QDUuzZN-7hgMK1EVcUoX23oQA0X8cbjEQ1RlvEZPYAiDyoa4QNsWzN4L1aPoilXfFo8ztc_loH-BYZroWO5rx9QFTyKncDu769P223kkvNMF0IlxhblxdKnfzuB?purpose=fullsize
 
https://images.openai.com/static-rsc-4/kEt046-Vx0ghj3H0WBUXN6IqarJMsgQXyY8eBeHkKpoDubMiQroielcXiZiBA2RVKHbcFZqMI6BcHGqehRjRFsUDadKaRP31bc3MLgXWxu5UcXBMHrzB6-jQZZRcS43UOA4c9VHfO7mK7HST1GXdcDEK1sXi_nYl7ekQMz1uhMVGAsHtQ7KXT-PAgNQf80yx?purpose=fullsize
 
5

Greenhouse gases absorb and re-emit infrared radiation, helping keep Earth's surface and lower atmosphere warmer than they would otherwise be.

Increasing atmospheric carbon dioxide concentrations strengthen this greenhouse effect and contribute to climate change.


The Carbon Cycle and Fossil Fuels

Carbon naturally moves between:

  • atmosphere
  • oceans
  • living organisms
  • soils
  • rocks

This movement is part of the carbon cycle.

Fossil fuels contain carbon that has been stored underground for very long periods.

When fossil fuels are burned, carbon is transferred into the atmosphere mainly as:

CO₂

https://images.openai.com/static-rsc-4/ihG4tm-j4SqWozzefWp8P7KCvTRayi-At8tLe99h2IkG5CbLFhZI1TveIdRIcOkohRoNHUoxn4zY2ZtoqUPayhOYOtlZ-m7azFhnmjTye6N7Bwt8-9AMp4tk4FcqQhDktUGmcxc4jFCKe6tR3NFCS2gTj7bP4BkrcN0WE1BqsDsG6jTbT0QQXttLKZ_N_jHU?purpose=fullsize
 
https://images.openai.com/static-rsc-4/0b06YCZj0LBs4DhXj55y_yY0SUyoCX1dVCf2gRwf7RTWDEaHHrylBXba2rR99A1DWFp6jSqd2fAQYZlQni9YfZyHDLQ8LqwGlmnsdqLbpP8Sp19qafpFewENVDgMHUgo6SAd_qagfyjbr53mWIsA3BQtFSIkhO4yUHgzx4piA5sf_Qgrch1swfI6P5-wauj-?purpose=fullsize
 
https://images.openai.com/static-rsc-4/QboBUaTDoHtyQb6QZRqzw6cp2cB-FYoWcssZVSDfTOf0cfBYPp7Wz1CUOlMOUz2uTuraGB7ILCnw4EQdk8q8DXJrgC4AFSp1Y_h2Y8RyTw6kIk3SqoE42dzZBiSXVfUhTVQ-cB5D-l9gpee5JtIk6ftPSk8b5e5tqaBbBGkbkUmcbiF5PO3lt3-67oDAbezF?purpose=fullsize
 
4

Large-scale fossil-fuel combustion therefore changes the amount of carbon dioxide in the atmosphere.


Air Pollution from Combustion

Combustion can produce several pollutants depending on the fuel and conditions.

These can include:

  • carbon monoxide
  • particulate matter
  • nitrogen oxides
  • sulfur dioxide if sulfur-containing fuels are burned
  • unburned hydrocarbons

Not all of these pollutants come directly from the alkane itself.

For example, nitrogen oxides can form when nitrogen and oxygen from the air react at the high temperatures found in engines and other combustion systems.


Nitrogen Oxides

Air contains large amounts of:

nitrogen, N₂

and:

oxygen, O₂

At very high combustion temperatures, these gases can react and form nitrogen oxides, often written collectively as:

NOₓ

https://images.openai.com/static-rsc-4/5PBjY1g9w3rwUln-eCTwg12UU30VWkt0Xf0wuRyBGYgz2H5l_C6GNWn9x7FSHoZzYL2lwqeHot0ncKcDCg3_f5SPpsTzpPO2ABCV7F7n9OFa6jtXN8aA-ZhWHmAkMmOFIS8vGZOwK5JW8h-7PXGerYQHKTXsQT93EU4eL6GtEx6EXEq6r_j6x6hGNWjmOW7b?purpose=fullsize
 
https://images.openai.com/static-rsc-4/fcXJDejhoqLYJKmVbZ9mlqbzOnt1mj1gQa68cEQRb2tObET4rlOPu2b8ATZo4iHnlRTyzyM9_ATBu76oeT4lPgB-tFLKDFiEleMWrQb5DtneirQn7Z9gl913xcF2klQAol1Hd-ZVjCxN7Gln11TMDSmCFXJ9PSb4qSoS8-GZoJ5y2QualAhDckXokX7Ohf1S?purpose=fullsize
 
https://images.openai.com/static-rsc-4/mrnJ3PTVKPV7g3a4MVw1A4dxTs-Wz6ZFNKtoCL_QWVvjZ8I4rM9k-0Fyucd1kSq3fgWuM-5IBITkE7pS1WAGE9kQ69SYHDS968FORm7QK7TWQMsbeRRno1F94ByX4fYL3hD0wMfkQtbI7oNUsFeTsdywUDC3aLWwMv_KxHba5o6sZTXk32skz6awIlCurLuO?purpose=fullsize
 
5

Nitrogen oxides contribute to problems including:

  • poor air quality
  • photochemical smog
  • acid deposition

Sulfur Dioxide

Some fossil fuels contain sulfur-containing impurities or compounds.

When sulfur is burned, sulfur dioxide can form:

S + O₂ → SO₂

Sulfur dioxide can contribute to:

  • respiratory problems
  • acid deposition
  • environmental damage

Pure alkanes themselves contain only carbon and hydrogen, so sulfur dioxide is not a product of burning a pure alkane.

It results from sulfur-containing material in the fuel.


Particulate Matter

Incomplete combustion can release very small solid or liquid particles into the air.

These are called:

particulate matter

Fine particles can penetrate deeply into the respiratory system.

https://images.openai.com/static-rsc-4/EpBiNMY3f6t8VFjfeFSM7Iy0_s0oA7z9UvhWDLSacFvecdk8u-mvtVZXdkz-HBSM0NGOA1ps6QVLMURjZdvwHp-rbGRGIhE26SaC7lc7mCjGCZU1bLVrVokNp-kfIS9frt144TCRv2KTH71dFl72YMwkj1qnVm2aHGGAOqBc0RAxHnJHroFg4QMoKwVm_XVv?purpose=fullsize
 
https://images.openai.com/static-rsc-4/L_Oj3FQIKWVQyQDj6Bkw5mMQqqTGsxb_-q3VRbNqUWwmrKLPHI3d0wFPA5dj40k9fr-lRxv9vhKL-fSkd5WV5UauI3R3CcuohZbFjoXXcGoBcpuEzAiGxWPVqNg_K36tgroKr9amw9AmQaNVXiiCGVAjaVNZsmKUqX_GMslQ3CaumdildcZu5DAB_3DBMWfl?purpose=fullsize
 
https://images.openai.com/static-rsc-4/GbtUIVib6U_JVc2KVDI262UDaKuHOcV0xOYq-HimiNj9K7Y6Jdtj5db8jybb8Rf7KD193McJ3e9tNPBe9_GKSvVnThelqN3h60ppZOzX3X-2r1PVpW6fKMchOYoGIrLNba7ddKo0JlDPo1Qg_9eplVH2tCQ5HazxNoObSqrcfcQMbsueo1nuXpyfO-KKyx7S?purpose=fullsize
 
5

Reducing incomplete combustion can therefore improve both fuel efficiency and air quality.


Complete Combustion Is Not Pollution-Free

A common misconception is:

"Complete combustion is clean, so it has no environmental impact."

Complete combustion reduces products such as carbon monoxide and soot.

However, hydrocarbon complete combustion still produces:

carbon dioxide

Therefore, complete combustion can still contribute to greenhouse-gas emissions.


Combustion in Vehicle Engines

Vehicle engines burn hydrocarbon-based fuels to release energy.

Ideally:

hydrocarbon + oxygen → carbon dioxide + water

Real engines may also produce:

  • CO
  • NOₓ
  • unburned hydrocarbons
  • particulate matter
https://images.openai.com/static-rsc-4/VWgjwEm2o135i5D5sVxk6IacxURAmWkmCjKgmMvnB6fK9jZ_JgGWG4DFcnkWX5ERxlTFc-6ofbexbS7F8fgkjeaI70E-JeirfFyHPBnwQVBwa8L7a6c768WoyDQZAQEcFEM0HauqmO3TU51XRy388mm70HU8MKs__RJrJzAuQZ56DlgwKAJ5gVGDeaFnLH_V?purpose=fullsize
 
https://images.openai.com/static-rsc-4/Ola6kRGYwcd_UvSPA5IQQcEXCrhVnHgMQ9HXGfRq9m30d4XL2I3QYqPapdt5kdRCR3I6XY56jwtKAiol10fwGWrjXFXzrKSF_3gscOmuSzyU-rGxYbr8dmVl5SzvGBiiyqB1CmBcnsdsP6J3JQMUSaPZiCiR3owmSEEPwyFzYeMvjA6Wq-f1U3weXRvCHjW1?purpose=fullsize
 
https://images.openai.com/static-rsc-4/fLkZGwHGy9vDSkvvMLS40DSqy-eHZJEv-ljyHDxMbwMubOAkZcwhNUqZCack99KWOnwUdAiRQoM8itjB0BpLZ0k2jedDhTEUA_jSgMRay4AZa_LdQZDNpSZsURVbS33azNwq2XBvZD7Stn_MVLOFn7oQIve7OQWmnWpW9onMRFBLTzYr7ppoVQM3ZOdmEBz1?purpose=fullsize
 
4

Modern engine and exhaust-control technologies attempt to reduce some of these pollutants.


Catalytic Converters

Many vehicles use a catalytic converter to reduce harmful exhaust emissions.

Catalytic converters can help convert:

carbon monoxide → carbon dioxide

nitrogen oxides → nitrogen

unburned hydrocarbons → carbon dioxide + water

They do not eliminate all environmental effects of fuel combustion, particularly the carbon dioxide produced from fossil carbon.


Combustion in Power Generation

Fuels may also be burned to generate electricity.

Chemical energy in the fuel is converted through several stages:

chemical energy → thermal energy → mechanical energy → electrical energy

https://images.openai.com/static-rsc-4/Mi9Q7PBvQb5zuBkQnkCom99hGVWuFzQrNUs0Lc9eVQC3mDqAiVOfhVV5jM-dKXdj4rXD1G0Iajq3QiklvXTCKBN6FToXwuxcRpa952SxY-9kw_5Zv_dTssleqeZ8jNOSnOqIzqmLsPGczrHK52wkXu3PJMKQ5r8omiJFpIEjYPTZypieHhmzcmITIEI-PtN8?purpose=fullsize
 
https://images.openai.com/static-rsc-4/mwNVukb4Q7fi8ZPOx_mIdLkOS3HQv6BxpJT4w4KdWzagsMJeNFOBdX-ABEs5KW9Juy4Vxiq8rsWvVGdrCtEV9ZxE66ggwetdQcTA04GP75MXesLTWYbj3y7dHPLVGCD7PFJfBvrWAnfeo_NNvingGPvEQYh4-91cg5A10ehM5jAhNXnzqFwxGOacbZZ9efO6?purpose=fullsize
 
https://images.openai.com/static-rsc-4/QmRmpav77sx_RfhQ1Nc8sSx2nPSXMs6wS9SLem057fM90SRuz6VRrsUt2x4lB4BBnvnI-Qj-aHP-z6GgR2r5kC1yQBIGCHxW8qaVaVCagh5Peh783WD2rVQGq6SAef-4P_UbmkUsrD_HWOw4rOIQSHxvrft67B5uLWve-mR_VJ_mxa2-PaTX4-ubpBxDqVZt?purpose=fullsize
 
5

Some energy is transferred to the surroundings at each stage, so the entire process is not 100% efficient.


Testing the Products of Complete Combustion

The products of complete hydrocarbon combustion are:

carbon dioxide

and:

water

Carbon dioxide can be tested using limewater.

Carbon dioxide causes limewater to turn:

milky/cloudy

Water can be detected using suitable chemical tests, such as cobalt chloride paper or anhydrous copper(II) sulfate in laboratory contexts.

https://images.openai.com/static-rsc-4/DoLQZvPwQO47e2nOliGSkqdxiVZVW5dewJerWJ0wuRJP-vJ4xQGZKg2bozHgA_F8pQ_Be-F2DaP0TFwxtADoPf1XBxdSEuPSilB-cYAsQNkKgTpCpEvylgZTF-bmwQtomDdU9oud5LwSbvbITpdtkPpB6siSk9TU3EbxWAZQIFrCEpliwLap115e6TMDGaqF?purpose=fullsize
 
https://images.openai.com/static-rsc-4/ut6MhvxTYQnNuxvO3CUk4UTSlz_7YO4ZwwSL-bQEpFmKR-GAQifA88IJXKBWPKmh7JSNnBClDH5KQVwSYexq_Dzq-w6Ynjgpp-MnujP0huNKf2DrpWVubgi3ci2ZA6jRRcApB9bSUPlXxwrOIloGAxpVb_pAdrzrK2dGwttSgYcfReslGETs3-j4QoD-svhc?purpose=fullsize
 
https://images.openai.com/static-rsc-4/kmeyZ3ShwbT21BbtDGKZ70mXonNnTZDNQxlpt9Toq4Vd-cUfaCMceWNXnirRnk1SLZlghbPyUCq5fFNgwpoJxp5Oyp3Le4bpbKFCNIyVlkmq51j6_QdeNMDCnGUEbhYkY3BqB51tmyV7z71klK9dvmohEwD_EG9380is5CVeHy_tKNZU2h8gokkJIyx_xwCY?purpose=fullsize
 
5

Balancing Strategy for Complete Combustion

Consider:

C₅H₁₂ + O₂ → CO₂ + H₂O

Step 1: Carbon

There are 5 carbon atoms.

Write:

5CO₂

So:

C₅H₁₂ + O₂ → 5CO₂ + H₂O

Step 2: Hydrogen

There are 12 hydrogen atoms.

Write:

6H₂O

So:

C₅H₁₂ + O₂ → 5CO₂ + 6H₂O

Step 3: Oxygen

Products contain:

5CO₂ → 10 O atoms

6H₂O → 6 O atoms

Total:

16 O atoms

Therefore:

8O₂

Final equation:

C₅H₁₂ + 8O₂ → 5CO₂ + 6H₂O


Another Example: Hexane

Start:

C₆H₁₄ + O₂ → CO₂ + H₂O

Balance carbon:

C₆H₁₄ + O₂ → 6CO₂ + H₂O

Balance hydrogen:

C₆H₁₄ + O₂ → 6CO₂ + 7H₂O

Oxygen required:

6CO₂ → 12 O

7H₂O → 7 O

Total:

19 O atoms

So:

C₆H₁₄ + 19/2O₂ → 6CO₂ + 7H₂O

Multiply by 2:

2C₆H₁₄ + 19O₂ → 12CO₂ + 14H₂O

https://images.openai.com/static-rsc-4/CWJpwvqcLXNr0IWzURWxtHdGB-09NHRjxNG6lyvLNDTUS8EsgQOBsyNumMhwUyVnxZiqlJcKxIFtYLa9N9xumeNEoQHLGheAwdHQmrv-TtZSAdYkiwHH_37xkgLYkjmiD2c1OcJOEre70iFZSiZRtstvalSIVHmizp3FUU8rUL3H6wBHug7yiBn4wg-ATsYL?purpose=fullsize
 
https://images.openai.com/static-rsc-4/Z8nYy0apABTazUKFl0SWRS_HgFCh_UeJhbjXwzoW0NDZLWEJM67jZnScRJ7-dB0jIswvFaPh7P_DOXECvBh5Ybs3Klzry1jPJ9uS9mOJENz8VEpqodVIahvF0YQtW90DYSiaJ6KZxoKDr_Y63wsQ-Pl_uPeevPoHH4DYFdxim3u3hXpkZEhFewE4w7Kl2vNK?purpose=fullsize
 
https://images.openai.com/static-rsc-4/8AdLPKFjCnH3ntv_wMxm-wXBiDkRmltJpo4QzQmp34Y2odtMqPFh4Q8z1LkB8LIbsv3KIP2EVN-YVns7iLHVrfgAlNjdEapJo0YOcoAs60rQu-6CLFbZUmFd5iFlb3Zf_dmCnQI1QrPyvedoSuqxzRhRcs0dHCYx0x0AJjNedcXi629zbbK5PhTx5aRpeXCa?purpose=fullsize
 

Worked Example 1: Identify the Reaction

Methane reacts with oxygen and releases heat.

What type of reaction is this?

Combustion

If sufficient oxygen is available and the products are CO₂ and H₂O, it is:

complete combustion


Worked Example 2: Identify the Products

What are the products of complete combustion of propane?

Propane is a hydrocarbon.

Complete hydrocarbon combustion produces:

carbon dioxide + water

Therefore:

C₃H₈ + O₂ → CO₂ + H₂O

Balanced:

C₃H₈ + 5O₂ → 3CO₂ + 4H₂O


Worked Example 3: Balance Methane Combustion

Unbalanced:

CH₄ + O₂ → CO₂ + H₂O

Balanced:

CH₄ + 2O₂ → CO₂ + 2H₂O


Worked Example 4: Balance Ethane Combustion

Unbalanced:

C₂H₆ + O₂ → CO₂ + H₂O

Balanced:

2C₂H₆ + 7O₂ → 4CO₂ + 6H₂O


Worked Example 5: Complete or Incomplete?

A hydrocarbon flame produces visible soot.

This suggests:

incomplete combustion

because some carbon has not been completely oxidized to carbon dioxide.


Worked Example 6: Carbon Monoxide

Why might a poorly ventilated fuel-burning appliance be dangerous?

Limited oxygen can cause:

incomplete combustion

which can produce:

carbon monoxide

Carbon monoxide interferes with oxygen transport in the blood.


Worked Example 7: Environmental Impact

A natural-gas heater burns methane completely.

Does this mean it has no environmental impact?

No.

Complete combustion produces:

CO₂

Carbon dioxide is a greenhouse gas.


Worked Example 8: Conservation of Mass

Consider:

C₃H₈ + 5O₂ → 3CO₂ + 4H₂O

Count the atoms.

Reactants:

C = 3

H = 8

O = 10

Products:

C = 3

H = 8

O = 10

The equation obeys the:

law of conservation of mass


Worked Example 9: Incomplete Combustion

Balance:

CH₄ + O₂ → CO + H₂O

Start by balancing carbon and hydrogen:

CH₄ + O₂ → CO + 2H₂O

There are 3 oxygen atoms on the right.

Use:

3/2O₂

Then multiply everything by 2:

2CH₄ + 3O₂ → 2CO + 4H₂O


Worked Example 10: Pentane Combustion

Write the balanced complete-combustion equation for pentane.

Pentane:

C₅H₁₂

Start:

C₅H₁₂ + O₂ → CO₂ + H₂O

Balance C:

C₅H₁₂ + O₂ → 5CO₂ + H₂O

Balance H:

C₅H₁₂ + O₂ → 5CO₂ + 6H₂O

Balance O:

Right side contains:

10 + 6 = 16 oxygen atoms

Therefore:

8O₂

Final:

C₅H₁₂ + 8O₂ → 5CO₂ + 6H₂O


Predicting Complete Combustion Products

For any alkane:

Step 1: Recognize that the fuel contains carbon and hydrogen.

Step 2: Check that sufficient oxygen is available.

Step 3: Carbon becomes:

CO₂

Step 4: Hydrogen becomes:

H₂O

Therefore:

alkane + oxygen → carbon dioxide + water

Then balance the equation.


A Reliable Combustion Equation Strategy

Step 1: Write the correct formula for the fuel.

Step 2: Add O₂ as a reactant.

Step 3: For complete combustion, write CO₂ and H₂O as products.

Step 4: Balance carbon atoms first.

Step 5: Balance hydrogen atoms second.

Step 6: Balance oxygen atoms last.

Step 7: If a fractional O₂ coefficient appears, multiply the entire equation to obtain whole-number coefficients when required.

Step 8: Count every atom on both sides to check the equation.

https://images.openai.com/static-rsc-4/ShQdxL11WGMJYDd--NJ9K614mmyguLC_asQrmR5piKOGIK8bcDDwcSrAK2Ri5f4h_lVdBayugnIzLw-fImI6lEL4e39pscRvVgOS3EGsZX6ZQ0LtBU4t8jWwioIlH5rYwYUjVz4Nm-LyflHoPZypZEeeOEgFZL9DPX1CxTAuIScubgrgsehv7sUBuaCuVbhK?purpose=fullsize
 
https://images.openai.com/static-rsc-4/zslXN82m7a0XbY8b2LrseibJrVaBsLuplcwNBmULnbzRi0iS4YGOaipvvdIj8c75vk4PRktoiXRzNfji0Byk6vYCcdDTVPxFgHcPlj3RKVNXPQ8tLhI1ZDoV7OcLV4RBtGhrN-1qwcRInSqHRW26LDwlhPAbIeBd8eizqb09RZOZLCnvbwO2C1rqAvqY2mlL?purpose=fullsize
 
https://images.openai.com/static-rsc-4/8daVe-54Mjii2C0XN2ULytZIdcP0xhbrbV5PXzEYoMKBMOt9S93aqQHFv_EglTSqbHVi_SUVEMoPJB5nU8bjDT8THXcfC1dr2_2_fojz8bVaMKBJdL1301a53wgDnzALPORTuYRd3yqjVN-NTQA5oV57kiiTynAEQ66it2z-KP0RACE1DL0ehfGPYRBJX0XC?purpose=fullsize
 
5

Complete vs Incomplete Combustion: Cause and Effect

Sufficient oxygen

↓

Complete combustion

↓

CO₂ + H₂O

↓

More complete release of chemical energy


Limited oxygen

↓

Incomplete combustion

↓

CO and/or C + H₂O, often with some CO₂

↓

Less complete energy release + additional harmful pollutants

This cause-and-effect relationship is important for understanding both chemistry and environmental impacts.


Environmental Impacts Summary

Combustion can affect the environment in several ways.

Carbon dioxide

  • greenhouse gas
  • contributes to climate change when atmospheric concentrations increase

Carbon monoxide

  • toxic to humans and other animals
  • associated with incomplete combustion

Soot and particulate matter

  • reduce air quality
  • can harm respiratory and cardiovascular health
  • black carbon can contribute to warming

Nitrogen oxides

  • contribute to smog
  • contribute to acid deposition
  • affect air quality

Sulfur dioxide

  • may form from sulfur-containing fuels
  • contributes to acid deposition
  • affects air quality
https://images.openai.com/static-rsc-4/ygZv2YtnCQJmg2mqXsb6L8nTXdwABrIOg_YAq__NXbfafpvzJBuQdc9p1GUcK4R8fmBElTx0CM-6ghz9IKy3ZQ5uShYetn_kN98kuHVDu0SvHQYl0sjYR3bBUt3w9W6Fu2spA_qPzc9xQ1T5MLovU1uj91BbZc6q_lKEMxTTSZ4mL7zn8AEcGzH74T_gGeJd?purpose=fullsize
 
https://images.openai.com/static-rsc-4/GPp7zQ1LBC4diutrR_6IzNLTlppqDeS6dTMmpvSHRiR0d7lSPUGYihwcX8HebIi2CX6xkLk3cNlVrlQoLGL4IdHZf7Oy44nAScklpU4WCzBNNTlBBoSz7rVPIyR5iOtVEXSNJ_33NvUTt70Rfx7T54hS7R3lhS2OqOt07pGmqWfQOGjkBz9Nn66aIQT3cPLv?purpose=fullsize
 
https://images.openai.com/static-rsc-4/xXzdog1BLhbkD67wl6i1k3FlcUlxpJSE0jLWBlR_D3Wn3CO7iDG_qQZHTtHuIi7yXKR0AyEk_JIXYvixa3HzkRC_u9hi-TlgdOP9jmFebLQf1CLLCHmJ3uQo1DPVQ9L1gFXrPGRKXFOXo9TUUM1djOpZKL4jM8m-df9w8sZSkqCqjo6t7xrRYrXB8A6GUdCq?purpose=fullsize
 
6

Reducing the Environmental Impact of Combustion

Several approaches can reduce combustion-related environmental impacts:

  • improving energy efficiency
  • reducing unnecessary fuel use
  • ensuring sufficient oxygen for efficient combustion
  • maintaining engines and combustion equipment
  • using catalytic converters and pollution-control systems
  • reducing sulfur in fuels
  • using lower-carbon energy sources where appropriate
  • replacing some combustion-based processes with renewable electricity
  • using public transportation or other efficient transport systems
  • developing cleaner industrial technologies

Different approaches target different pollutants, so there is no single solution to every environmental impact of combustion.


Common Mistakes

Mistake 1: Saying combustion means burning without mentioning oxygen

Combustion involves reaction with:

oxygen


Mistake 2: Saying complete combustion produces carbon monoxide

Complete hydrocarbon combustion produces:

CO₂ + H₂O

Carbon monoxide is associated with:

incomplete combustion


Mistake 3: Forgetting water

Hydrocarbons contain hydrogen.

During combustion, hydrogen forms:

H₂O


Mistake 4: Changing subscripts when balancing equations

Never change:

CH₄

into:

CH₂

to balance an equation.

Changing a subscript changes the substance.

Change coefficients, not chemical formulas.


Mistake 5: Balancing oxygen first

For hydrocarbon combustion, it is usually easier to balance:

carbon → hydrogen → oxygen


Mistake 6: Thinking a yellow flame always proves exactly which products are present

A luminous or sooty flame can indicate incomplete combustion, but actual combustion products depend on the fuel and conditions.


Mistake 7: Saying complete combustion has no environmental effects

Complete hydrocarbon combustion still produces:

carbon dioxide


Mistake 8: Saying pure alkane combustion directly produces sulfur dioxide

Pure alkanes contain only carbon and hydrogen.

Sulfur dioxide comes from burning sulfur-containing material.


Mistake 9: Thinking carbon monoxide can be detected by smell

Carbon monoxide is:

colourless and odourless


Mistake 10: Forgetting conservation of mass

Every balanced chemical equation must contain the same number of each type of atom on both sides.


Did You Know?

Combustion has powered human technology for thousands of years, from early fires to modern engines and power stations.

https://images.openai.com/static-rsc-4/8MuAwS3s8_QvvFAcfDhOmw8Sn2tIlZB60_y4ZeezGUJSU5ZQbAaYFFylxKiacsPb6hkIpQ8mh7CSdCNiH9Aly8cTkxM5uLvIy9HUWDk6nv578tppK350o2aR4GIXgFHZ76gvy3YrGv1lBAK4H8kQxGAB9HcQBfClVBCeP23ua48gaz5dHOwb5_WfogXWM0FD?purpose=fullsize
 
https://images.openai.com/static-rsc-4/jo_4Es23zfLSX7yQfFvx4VEPSbZFxz1QQJfyNRPT-n5u8xaPnw5MBY4PGXfQbqauc4WnKevZdalF0EvY2tYnXENVoETDy04htCAIwIFab-BPKQkRQ1fX0CWzWQ_RnATUu24hC80oWSYQLg9XiJP8zJAGiR7M7Fs1vMVhFs_BX9dT45GAYr0Zbx0w6o9Gwwxc?purpose=fullsize
 
https://images.openai.com/static-rsc-4/KxRrYuL2Gdn_DUyQjwiP-GlO9cMoBWmn4Wp_XQK5K_AS_diTK-8AS-wByr4bH5E66ykhdISPNNWN28NulHErXEtE9CXJoSGZmFyAUGRvNnOq_CkXCMQKXbCzDxGttoKLNbz8oOFH-vEEh9j2DfOtrzSBo4NGsyzcNOLuF4wcyZatABpdqYmrihRArDpf4xfZ?purpose=fullsize
 

However, the large-scale combustion of fossil fuels has also created major environmental challenges.

Understanding combustion chemistry helps scientists and engineers design systems that:

  • use fuel more efficiently
  • produce fewer harmful pollutants
  • reduce greenhouse-gas emissions
  • recover more useful energy
  • transition toward alternative energy technologies

Combustion chemistry therefore connects molecular reactions with some of the largest energy and environmental issues faced by society.


Key Terms

  • Combustion: Reaction of a substance with oxygen that releases energy.
  • Fuel: Substance used to release useful energy.
  • Hydrocarbon: Compound containing only carbon and hydrogen.
  • Complete combustion: Combustion with sufficient oxygen.
  • Incomplete combustion: Combustion occurring when oxygen is insufficient for complete oxidation.
  • Exothermic: Describes a reaction that transfers energy to the surroundings.
  • Carbon dioxide (CO₂): Product of complete hydrocarbon combustion and a greenhouse gas.
  • Carbon monoxide (CO): Toxic gas that may form during incomplete combustion.
  • Soot: Carbon-rich particulate material that can form during incomplete combustion.
  • Particulate matter: Tiny solid or liquid particles suspended in air.
  • Greenhouse gas: Atmospheric gas that absorbs and re-emits infrared radiation.
  • Nitrogen oxides (NOₓ): Pollutants that can form during high-temperature combustion.
  • Sulfur dioxide (SO₂): Pollutant produced when sulfur-containing material burns.
  • Catalytic converter: Device that reduces several harmful vehicle exhaust pollutants.
  • Fossil fuel: Carbon-rich fuel formed from ancient biological material over geological time.
  • Conservation of mass: Principle that atoms are rearranged but not created or destroyed in chemical reactions.

Key Equations

General complete hydrocarbon combustion:

hydrocarbon + oxygen → carbon dioxide + water


Methane:

CH₄ + 2O₂ → CO₂ + 2H₂O


Ethane:

2C₂H₆ + 7O₂ → 4CO₂ + 6H₂O


Propane:

C₃H₈ + 5O₂ → 3CO₂ + 4H₂O


Butane:

2C₄H₁₀ + 13O₂ → 8CO₂ + 10H₂O


Pentane:

C₅H₁₂ + 8O₂ → 5CO₂ + 6H₂O


Example incomplete methane combustion producing CO:

2CH₄ + 3O₂ → 2CO + 4H₂O


Key Takeaways

  • Combustion is a reaction between a fuel and oxygen.
  • Combustion reactions are generally exothermic and release energy.
  • Alkanes are important hydrocarbon fuels.
  • Complete combustion occurs when sufficient oxygen is available.
  • Complete combustion of hydrocarbons produces carbon dioxide and water.
  • Incomplete combustion occurs when oxygen is limited.
  • Incomplete combustion may produce carbon monoxide, carbon/soot, water, and some carbon dioxide.
  • Carbon monoxide is toxic because it interferes with oxygen transport in the blood.
  • Soot and other particulate matter can reduce air quality and affect health.
  • Combustion equations must obey the law of conservation of mass.
  • A reliable balancing order is carbon → hydrogen → oxygen.
  • Coefficients may be changed when balancing equations; chemical subscripts should not be changed.
  • Carbon dioxide from fossil-fuel combustion contributes to increased atmospheric greenhouse-gas concentrations.
  • High-temperature combustion can produce nitrogen oxides.
  • Sulfur-containing fuels can produce sulfur dioxide.
  • Complete combustion reduces CO and soot formation but does not eliminate the environmental effects of burning fossil fuels.
  • Understanding combustion connects chemical equations with energy production, air quality, climate, transportation, and everyday fuel use.
 
 
 

5. Crude Oil and Fractional Distillation

Learning outcomes
  • I can describe crude oil as a mixture of hydrocarbons.
  • I can explain how fractional distillation separates crude oil into useful fractions.
  • I can identify the major fractions produced during distillation.
  • I can relate hydrocarbon chain length to boiling point.
  • I can explain the importance of petroleum products in modern society.

https://images.openai.com/static-rsc-4/dfkzVOSk1ceNY5DPP1USVCXXYcrV_g1qWgBfk0LnggMrLcW1qF0KtxvSY_e9Sk8ab7P8WmjDUrCfG36Ae5QVZK2vxINpVAG__hZW6U_FJ4Z6_SJbOg-u6INCco4TMxLHEmOi765jEOmTm_2gxD4ydR1E8Kf6TLLxZ-HRg2F-pmeOvJ9CrdQbm4dQWeuGvt11?purpose=fullsize
 
https://images.openai.com/static-rsc-4/ATVcDqFd2MT05GXRCnMzYOmHkYsDhuFqOidqrwBiq5gzBxuFFeZ-i1zIT7O5bO6_ZaHui305QP_UlAqjGFFQbsmjBjKEnQKZkaEtjajkzSK7OLKmrmXQStBfMUiZm09YKlulMf3o-lIm2EHz-MthfF3j92DZtyyB9UqyMU4WYXBCBfX3lUZCNgJbYFL8EX0t?purpose=fullsize
 
https://images.openai.com/static-rsc-4/SxNQvq6OL1StkaCd0CAG5VwzXHVtBnHKcNbEbiJIXCnN6pfb0Vi3MfkeJXZeyMmGVQva26N440e34Lg36UOh0EOcAKMwGTQ_WJ0ouv3T8ctM-w4GMTywFpOh4QMlIt_DweKUmPrcgTo24_3dae7eEeFq8X5m6Y-poS5bxNYUvNmNo6TqtQQnjS7j31njo5Oi?purpose=fullsize
 
5

What Is Crude Oil?

Crude oil is a naturally occurring liquid mixture containing a very large number of different compounds.

Most of these compounds are hydrocarbons.

A hydrocarbon contains only:

  • carbon
  • hydrogen

Many of the hydrocarbons in crude oil are alkanes, although crude oil also contains other types of hydrocarbons and small amounts of compounds containing elements such as sulfur, nitrogen, and oxygen.

Crude oil is therefore a mixture, not a single pure substance.


A Mixture of Hydrocarbons

The hydrocarbons in crude oil have different:

  • molecular sizes
  • carbon-chain lengths
  • structures
  • boiling points
  • viscosities
  • volatilities

Some contain only a few carbon atoms.

Others contain dozens of carbon atoms or more.

https://images.openai.com/static-rsc-4/lm9ONTc0iJfTySj1cHof0yDgiXbBQBmhB0vVHPDBVtweU8PtZteTCqpQjuYUVhIvi1czfuuk1yTCqnvL8WUWF0pF9kg6-H7TzDEvLS8Ws2j-4VN8GUPvNZ6GfyHeQDW5Nc3X50nYCFMPYP7j7N8NHeULFDEgDesHXWshclwR6jvOobwb5l676Qtk6i3s0p9h?purpose=fullsize
 
https://images.openai.com/static-rsc-4/CP3g_ecMRxVQvbdoyy3_oLEPGDn64GSRbC0OUIj4REQsn_UVY5PjlUOQZKkP8XcOK1fppwPUy-O2bHeWHnK7qBIrhjWkyP1B4Q7FBX2MvwnfxTJ8Fx9Yiu8rDQ2AdTZqiRcSlslzaIa4_Fhd-8Bk_mJnap8NoZUYPj8NGh-Q4trST59EEQRP6Raq9q5eBbrl?purpose=fullsize
 
https://images.openai.com/static-rsc-4/PnN_DPT4L9trN3tX6XRE9GeHNctun2Qb-kJa_XkI8db2uBhAKbF_CwH6Vz0wXPbtQB_KRzadnXIwv86D8hPGw3g-qEk-PrshoXN1agTNeEglAmw2dQmV8bRaM3dWKU_aBZR5l1mpkYBKd6PGE5DnDIu_NB26hx6xbwxJny5zYo8i1ypNO-H44QdZzGFwtcw_?purpose=fullsize
 
5

These differences in physical properties allow crude oil to be separated into useful groups.


How Crude Oil Forms

Crude oil formed from the remains of ancient organisms that were buried beneath sediments.

Over millions of years, conditions involving:

  • burial
  • pressure
  • heat
  • geological processes

helped transform organic material into petroleum and natural gas.

Because crude oil takes geological timescales to form, it is considered a non-renewable resource on human timescales.


Why Crude Oil Must Be Separated

Crude oil itself is not usually the most useful form of petroleum.

Instead, industry separates it into groups of hydrocarbons with similar properties.

These groups are called:

fractions

Different fractions are useful for different purposes.

Examples include:

  • fuel gases
  • gasoline
  • petrochemical feedstocks
  • kerosene
  • diesel
  • fuel oil
  • lubricants
  • waxes
  • bitumen
https://images.openai.com/static-rsc-4/nP8WUg864wTc8I4BiwXu6gx1Iw7lWwBAVWvItUmdvc_lL7Hp2LVtr03U5daPJF0c-kfIIySvWtzNOm5kz60Y9S0fLbYTA80oS_Nq7j3CdSB79hglVoEA3LPD8P68evZ31_pzuJ_TTgMucyPr5tT2OCViZXNGpARa7vFfJeM5dDBZTXJBEOAw4r7XzrJ2dkxV?purpose=fullsize
 
https://images.openai.com/static-rsc-4/oV31KJMBH6wvuZnp_17_Saj67iY-YSIvsdOKJKECI2efJZjn0r5nwbPDjUD2VeHx8fbqYuD6mvokW47rrjWNtXZXm3B0owwbyLEc9hiUAGPEqxK_y0akkEFNi55k4NZe559ShJ0_jIo8o91WKuIY-76-54u39nDA2PTsayXOERlOq0-MT11RrCPm_tUSLVGv?purpose=fullsize
 
https://images.openai.com/static-rsc-4/7S5pHuLXG9bf8AA3b_thjsrVXoTsLysm_CtUDnw2YuoW__EzKHVYiMpvaeNlN7gTV9sAD1IRlV_M1SiOxxuuCFxArDRueIXTwbq_HD-yI3ZYbcx1LGwOHPS5eOdCDa53u1hHk2rMDjB5IwT81b0yO1dB6WEbAjZqWBtoQcXcVw8GRjTS3Uw2TdAkdUJu0Zrv?purpose=fullsize
 
6

What Is a Fraction?

A fraction is a mixture containing hydrocarbons with a similar range of:

  • boiling points
  • molecular sizes
  • carbon-chain lengths

A fraction is therefore not normally one pure compound.

For example, a gasoline fraction contains several different hydrocarbons with boiling points within a useful range.


Fractional Distillation

Crude oil is separated using:

fractional distillation

Fractional distillation separates substances because they have different boiling points.

The process takes place in a large:

fractionating column

https://images.openai.com/static-rsc-4/lXZNn8kIxV76og2DlIe_85qyilTpfjVcpMySDyrQAvMH5JOEXOdVM5Zh7grg0ubUpSAzU9gI9vKBCQ2TD09t-rwm-UH0liutzjYcV2U8JPgk7IqWVJRAhBGZncU1y0VX9eDvw6Oa-8L7cZSJYd3X40oDDooa3kQaDatZ8iYtm3ajQSgw__zAscIEpeAUFrIj?purpose=fullsize
 
https://images.openai.com/static-rsc-4/ccFjZd6ubOIbkgMMwFeKwy3niEKlPEx_FveFdIeMOJQPB3AH7HAKWCg0f7MZ13W-SUJ25-2E9624rODWjXXsoFtx7G5FnUIL-nuVt2FD0kzoNGbsOycAa65TQ8KaTP6Kt9HbdvNXO2ffYatSZCfqLUiCn91aDB7zNfLD0tnr2npCgdb5zjXVF4-dn04OzmvN?purpose=fullsize
 
https://images.openai.com/static-rsc-4/CP3g_ecMRxVQvbdoyy3_oLEPGDn64GSRbC0OUIj4REQsn_UVY5PjlUOQZKkP8XcOK1fppwPUy-O2bHeWHnK7qBIrhjWkyP1B4Q7FBX2MvwnfxTJ8Fx9Yiu8rDQ2AdTZqiRcSlslzaIa4_Fhd-8Bk_mJnap8NoZUYPj8NGh-Q4trST59EEQRP6Raq9q5eBbrl?purpose=fullsize
 
5

The column is:

hot at the bottom

and:

cooler toward the top

This temperature gradient is essential to the separation.


Step 1: Heating the Crude Oil

Crude oil is first heated strongly.

Much of the crude oil:

vaporizes

The hot mixture of gases and vapours enters the fractionating column near the bottom.

Very large hydrocarbons with extremely high boiling points may remain as liquids or residues.


Step 2: Vapours Enter the Column

Inside the fractionating column, the temperature decreases with height.

At the bottom:

temperature is high

Near the top:

temperature is much lower

https://images.openai.com/static-rsc-4/7KcnRE5vnjJ8MwFOwS4CZqQ66cxUj37Ay3LNf1_jyTrDElVfaHH1SLzSUhWCAYY0mDJn7PA6jk6qk-eIHlHdIcUAmQwo7zZ9h9rBOkFNICYXm6O4UXfCO30JjqtlAnnd6nU0R4ofWCM5vu1jy52zXCkOkMr10H1OCKTSsL9jSqSm8Mgtlxx6jXVXQ-TL0Cf3?purpose=fullsize
 
https://images.openai.com/static-rsc-4/lXZNn8kIxV76og2DlIe_85qyilTpfjVcpMySDyrQAvMH5JOEXOdVM5Zh7grg0ubUpSAzU9gI9vKBCQ2TD09t-rwm-UH0liutzjYcV2U8JPgk7IqWVJRAhBGZncU1y0VX9eDvw6Oa-8L7cZSJYd3X40oDDooa3kQaDatZ8iYtm3ajQSgw__zAscIEpeAUFrIj?purpose=fullsize
 
https://images.openai.com/static-rsc-4/HW5SvIDGcnldfurE-rocz4NIkycGNh5q1_nGvliHF6q9RBprltfeuvGflf3TABMK9nuEYkVKja71yi0iy_qpoz8ctTEujQJpEpKPX-ZcHKHRXDWCFQ4WzOM6Yu0P28lap6TQ23CpvaQA5mWS1EN9OdULVzE5yX9ihrtK_fbNecGx7tEzC1g2KHtk14sDl1wa?purpose=fullsize
 
5

Hydrocarbon vapours rise through this temperature gradient.


Step 3: Vapours Cool

As hydrocarbon molecules move upward, the surrounding temperature decreases.

Eventually, each hydrocarbon reaches a region where the temperature is low enough for it to:

condense

Condensation is the physical change:

gas → liquid

Different hydrocarbons condense at different heights because they have different boiling points.


Step 4: Fractions Are Collected

Hydrocarbons with similar boiling points condense in similar regions of the column.

They are collected together as:

fractions

Therefore:

high-boiling hydrocarbons condense lower in the column

while:

low-boiling hydrocarbons condense higher in the column

https://images.openai.com/static-rsc-4/OlqU8IaRlWMqxfbhQtKZeskbKVs9jw9643tdi6diaPfgUyX-D78cKlFP35SZ2PMFTSYxIuXWOzbK3jFXod-oJ0f_7m6SCWKt7H0p1BEYYzeWlzjtECkSormtZp86eVvNDgIU6XV0Xyx4w6d1yOlB6y6N9ENTxYEhcm809mBEMBo7l-7USMH2JJfsPSCFNBfk?purpose=fullsize
 
https://images.openai.com/static-rsc-4/hC69OL2SXdYSk0tJNJ_p4s15VoDIKh2bhX7bFeqY4OIuTH4SQwCGTwyZWCur808EiiXAOOiKWlBB10Zu0_lOWL0BzgJ2EO15DmpoBLBl_gG6mscsyTxj_OKentjYyAVHRuhk5Ou86jsBb3o-63ldpc5aL5pV7E_-qFN-KKd0l4CuvTaZmr_SbFjs9WpMIIU-?purpose=fullsize
 
https://images.openai.com/static-rsc-4/NfdRo_VfDIGPFBdxflgwpP2OGZ5fjl3-ev-qlBhRhMxfdOFXjIxIqe7kYTEPBcJ9yB1r2XJvg92v5r83QOzFxStKurQI__iiKZH5gpE5XNlwEzW6TmAjVuIQoS0TNz-s54SyDDmp_oZBHgsj2NHN2y1f2BCE-vwpmTyYzTlE6zXA115Vvoj7-FNyxPHSlbGU?purpose=fullsize
 
5

Very small hydrocarbons may remain gases even near the top and leave the column as refinery gases.


Why Fractional Distillation Works

Fractional distillation works because the hydrocarbons in crude oil have different:

boiling points

The boiling point depends partly on molecular size and intermolecular forces.

As hydrocarbon molecules become larger:

  • they contain more electrons
  • their electron clouds become more polarizable
  • London dispersion forces become stronger
  • more energy is required to separate the molecules

Therefore:

longer hydrocarbon chain → generally higher boiling point


Chain Length and Boiling Point

Consider these alkanes:

Methane:

CH₄

Butane:

C₄H₁₀

Octane:

C₈H₁₈

Hexadecane:

C₁₆H₃₄

As carbon-chain length increases, boiling point generally increases.

https://images.openai.com/static-rsc-4/4fT0EDaQI7bdJuUN_3czjb0LH7-M6fro1y0nXGNVSb8eiD78TTWl8nYf0eOk7Z3cdWqhS6eucKDKS9XW_-AEU05M6LDmmd_xbjaVwxr7cAN7M_rtg71yncNMJJYpbade5R_HCOdexa0DLfOTbcrjOgjiw6p1b3HwY0bBHN52LlhqRYqp4pnW3ProcxIamWkA?purpose=fullsize
 
https://images.openai.com/static-rsc-4/EPbdY2dya7Z5ZheplqAcMboW3oVGg4nZ0zeolM8yuF5a8zhvA4F0mCIlVihRs5Eu8-y37LHVImyEpnt4p7zxzMetc_ES3RRcXfmCTH5eobExN5AxLhImSwoCI52c4DGxUm9LjDPxWxwVn3BoH6Vn_Lj6aYp8HGZvBsVxJYc5ReBJ-I3cNGuckpwwWSJwW8Ci?purpose=fullsize
 
https://images.openai.com/static-rsc-4/xcm7j10lQMQJ8RqKzUNX1cpu6rMT91QOlFHGeKylexF4CuBXVzPksXMOAZp6s0WbcXOwnmX7Y60uambU91-8IEmmEnopSyymOF3iF-BzBp8Gq-C8mvJurOR-g9CZf0oMmufljgHNzhdmDbq7nnT13A7gdWG97scwGp7w7sCSRkw4V2AezpbebaAGgXEOZQz_?purpose=fullsize
 
4

This relationship is one of the key ideas behind fractional distillation.


Intermolecular Forces

Hydrocarbon molecules are generally nonpolar.

The main attractions between them are:

London dispersion forces

Small hydrocarbons have relatively weak dispersion forces.

Large hydrocarbons have stronger dispersion forces.

Therefore:

small molecules → lower boiling points

large molecules → higher boiling points


What Happens Inside the Column?

Imagine three hydrocarbon molecules.

Hydrocarbon A

Short chain

Low boiling point

Travels high in the column before condensing.

Hydrocarbon B

Medium chain

Intermediate boiling point

Condenses around the middle.

Hydrocarbon C

Long chain

High boiling point

Condenses low in the column.

https://images.openai.com/static-rsc-4/ccFjZd6ubOIbkgMMwFeKwy3niEKlPEx_FveFdIeMOJQPB3AH7HAKWCg0f7MZ13W-SUJ25-2E9624rODWjXXsoFtx7G5FnUIL-nuVt2FD0kzoNGbsOycAa65TQ8KaTP6Kt9HbdvNXO2ffYatSZCfqLUiCn91aDB7zNfLD0tnr2npCgdb5zjXVF4-dn04OzmvN?purpose=fullsize
 
https://images.openai.com/static-rsc-4/NfdRo_VfDIGPFBdxflgwpP2OGZ5fjl3-ev-qlBhRhMxfdOFXjIxIqe7kYTEPBcJ9yB1r2XJvg92v5r83QOzFxStKurQI__iiKZH5gpE5XNlwEzW6TmAjVuIQoS0TNz-s54SyDDmp_oZBHgsj2NHN2y1f2BCE-vwpmTyYzTlE6zXA115Vvoj7-FNyxPHSlbGU?purpose=fullsize
 
https://images.openai.com/static-rsc-4/hC69OL2SXdYSk0tJNJ_p4s15VoDIKh2bhX7bFeqY4OIuTH4SQwCGTwyZWCur808EiiXAOOiKWlBB10Zu0_lOWL0BzgJ2EO15DmpoBLBl_gG6mscsyTxj_OKentjYyAVHRuhk5Ou86jsBb3o-63ldpc5aL5pV7E_-qFN-KKd0l4CuvTaZmr_SbFjs9WpMIIU-?purpose=fullsize
 
5

This allows thousands of compounds to be separated into manageable groups.


Major Fractions of Crude Oil

The exact names and boiling ranges used for fractions can vary between refineries and textbooks, but a simplified school-level sequence from the top to the bottom of a fractionating column is:

Refinery gases

↓

Gasoline / petrol

↓

Naphtha

↓

Kerosene

↓

Diesel / gas oil

↓

Fuel oil

↓

Lubricating oils and waxes

↓

Bitumen / residue

As we move downward:

carbon-chain length increases

boiling point increases

viscosity increases

volatility decreases


Refinery Gases

Near the top of the column are the smallest hydrocarbons.

These are often called:

refinery gases

They contain very short hydrocarbon molecules.

https://images.openai.com/static-rsc-4/YjfC6OmJnGbwNs-yyaKzlP_ZddEzK1dIIzyqZ2Li-NDLpKwhClaYeU9CI1y0I7-Fisbgl81fIVYX7beZMcqFJ2-WkPMqXvERTHMNxoDz50gUml6t7Rjl9dMbCtvoFeuV5jLJs9edCe3KKL45U2F3cSbYMLHeaJJBAt6GursdTlrA-vWqYtoKMN-lmDIDJDn6?purpose=fullsize
 
https://images.openai.com/static-rsc-4/deIhEjtmRUqOUGEZaYWwWK7kM8wD1z0zdMyG6cmnoVrWO0bLW578WHQuGlp4V3K8trAZNY1BmlXXrltjYJZtXvdC8iAwk4sIK_5elvZQ4jvx3xV2BibrpINfuc_B0iYjru4mZmXrz2TXmGxo7U8sJYtYQzKjLUntBVpH9yKkGjsY5jT1jfV4-ii4EtqGGb7E?purpose=fullsize
 
https://images.openai.com/static-rsc-4/oUpagQfBeOS12IOZtIhdqK1Nq9sKFnMcG3IqcakaD6FkvnL9jvwdHBER8U6ey8pP8k6MYqP810TVaMCHR7OOb9PZ0KrosBMfLbVaKKPtpUtmBPYTVv4wk9PtbPPFp4yDtMEZwuwSaPXftIEI8c48KN6TgTXkqJF4sD-iU_jaG6J8A-gQbQujcoEd3e_cuKF5?purpose=fullsize
 
4

Properties include:

  • very low boiling points
  • high volatility
  • low viscosity
  • gases at ordinary conditions

Uses include:

  • heating
  • cooking
  • LPG

Propane and butane are important examples.


Gasoline or Petrol Fraction

The gasoline fraction contains relatively short-chain hydrocarbons.

Properties include:

  • low boiling points compared with heavier fractions
  • relatively high volatility
  • low viscosity
  • easy ignition

Major use:

fuel for spark-ignition vehicle engines

https://images.openai.com/static-rsc-4/deIhEjtmRUqOUGEZaYWwWK7kM8wD1z0zdMyG6cmnoVrWO0bLW578WHQuGlp4V3K8trAZNY1BmlXXrltjYJZtXvdC8iAwk4sIK_5elvZQ4jvx3xV2BibrpINfuc_B0iYjru4mZmXrz2TXmGxo7U8sJYtYQzKjLUntBVpH9yKkGjsY5jT1jfV4-ii4EtqGGb7E?purpose=fullsize
 
https://images.openai.com/static-rsc-4/ccFjZd6ubOIbkgMMwFeKwy3niEKlPEx_FveFdIeMOJQPB3AH7HAKWCg0f7MZ13W-SUJ25-2E9624rODWjXXsoFtx7G5FnUIL-nuVt2FD0kzoNGbsOycAa65TQ8KaTP6Kt9HbdvNXO2ffYatSZCfqLUiCn91aDB7zNfLD0tnr2npCgdb5zjXVF4-dn04OzmvN?purpose=fullsize
 
https://images.openai.com/static-rsc-4/xG4WLINut9woe78KCgqyCRTkDFzVRL5XOdyY7So6SRwlR-F4bwXUGsyyL0OmhFalMeQTHEEMs3mk2_6muNXRfFCrysMmU233sbn5_jrAI-Rek7TXrQyTnxl1jxAbBglT-nAgNilV61DEMDh1oNv2Xf0bSjcYqnLJ_m3sUv-plebTWMxDuQFE-hrpXDA7LJC0?purpose=fullsize
 
5

Its ability to vaporize relatively easily is important for its use as a fuel.


Naphtha

Naphtha is an important petroleum fraction used largely as a chemical feedstock.

It can be used to produce chemicals that eventually become:

  • plastics
  • solvents
  • synthetic materials
  • other useful organic compounds
https://images.openai.com/static-rsc-4/0cOh458YyV6IUQ3ip1sv0Y9DoulB-9gA2PuTWqCw52XdQiEgJmipT2_gRrn863WkFmp9IG1jpa3GRRDkOU0uSFMUrgnh8eELkhx891pai51aj0yNLC8gxd4nWbRWDs8xl9Vpq2cu0F_P8W3-Ulgdvp85O1iMViAQIO1XxzfG803GqMmL3EuYHzwIYeti4cI6?purpose=fullsize
 
https://images.openai.com/static-rsc-4/tfasdX3RKBJkf8_xZWSKCieIvTTXHRaxNhkVUaNYz-5VvVeKzxIiF6HmjdCts6f0eIOxnN9spKP6q--uARMxW9Gn2A9LDYRPCUYDDedDK1ljM_Zle3BPXLacm4YAizujAGZiSXxB5DZd9Nrp57TOnxQMeLfteWZvdZIzDG8tSuzt6iITc2_0u1JE2tmwfGJy?purpose=fullsize
 
https://images.openai.com/static-rsc-4/K9r6zt03Z644hNZ7qfJlWDJKBr_5osgrI0K_KKpmhWLaj8kpzZm_QGNAMqIl7MxXMsBYREJkPLUQ1eU66lVKScsZPPST-9cjHCb1CdLMMDFyQ4_SkHsq8yIt76R2sF4eOMFosRMrRXmlzXC7W5Q7MGA4wBSsLyS-yRV3TaPSSmuMMcTNC53FxqtN3qcREQpY?purpose=fullsize
 
5

This illustrates an important point:

Crude oil is not used only to produce fuels.

It is also an important source of raw materials for the chemical industry.


Kerosene

The kerosene fraction contains larger hydrocarbons than gasoline.

It has:

  • higher boiling points
  • lower volatility
  • greater viscosity

One major use is:

aviation turbine fuel

Kerosene-type fuels are also used in some heating and lighting applications.

https://images.openai.com/static-rsc-4/hC69OL2SXdYSk0tJNJ_p4s15VoDIKh2bhX7bFeqY4OIuTH4SQwCGTwyZWCur808EiiXAOOiKWlBB10Zu0_lOWL0BzgJ2EO15DmpoBLBl_gG6mscsyTxj_OKentjYyAVHRuhk5Ou86jsBb3o-63ldpc5aL5pV7E_-qFN-KKd0l4CuvTaZmr_SbFjs9WpMIIU-?purpose=fullsize
 
https://images.openai.com/static-rsc-4/v-0WWolggPwS052NeYXbBs--A9HZHenzLjWvp8K3Exoqv8FxokRpuDIjI9NuUl5iR6mR5o8j_vSUWkqN4-ZoHAWD_gIehw-UPXZHOZEe2Yi3JKzknYgj_BdtBNk8qek34lwbkzeBYaGyT-emNLDdhg4b4Ku__FFzBafsbSdyaZ-vymRW6MCJzDssRKu-yqBS?purpose=fullsize
 
https://images.openai.com/static-rsc-4/xtp6ZCFZVyV28dYkoaUSyc6dCRiPQKbj5Z8n02D1WZKkchKFX2XJYQxtKJ7muOA20bu5F1JwIarVfLRE1e2goUjnWpjPYmyKysihUbOomC3WlVkkeb85YBiLcMTuwLQvoHDtJCH5i6gjp2hfpdIwRh_V-eAggLoRCxBI-hnOs500a7FHc0vlGfH-R_SoMT4z?purpose=fullsize
 
5

Diesel or Gas Oil

The diesel fraction contains still larger hydrocarbon molecules.

Compared with gasoline, diesel generally has:

  • higher boiling points
  • lower volatility
  • greater viscosity

Uses include:

  • diesel engines
  • heavy vehicles
  • machinery
  • some heating systems
https://images.openai.com/static-rsc-4/_kN11TjP2HPQzy6F4sGcO0rp145uh9QxaO33tNs19dKPhEwV8TNRwqsyHvJelescfvYJs5QN84eJJz51Iq4TBoTI3iV9mMun-Qvy80beXj4ohL7mjtFUJV64yV8AojjG938fsyWRHfqaCz_Oqn78dmGz5NL-fUqHE43afzTGoCYvbAxvFenH60wRrcGcY8wJ?purpose=fullsize
 
https://images.openai.com/static-rsc-4/dfkzVOSk1ceNY5DPP1USVCXXYcrV_g1qWgBfk0LnggMrLcW1qF0KtxvSY_e9Sk8ab7P8WmjDUrCfG36Ae5QVZK2vxINpVAG__hZW6U_FJ4Z6_SJbOg-u6INCco4TMxLHEmOi765jEOmTm_2gxD4ydR1E8Kf6TLLxZ-HRg2F-pmeOvJ9CrdQbm4dQWeuGvt11?purpose=fullsize
 
https://images.openai.com/static-rsc-4/E5a0z2chm4Pg6WkisPmUQeXqvljEAcRQhDIH6nzJpUVPV38DrEAPicyAwJEWcxweKzyQQJ7DPMVEIyME4zQ4DulPNYKhNOy2SEhlxKILbFs95wNGjeNKcJlkxpOpBvlfcbrptnOg0ENOxSsca_7MAug6mBV9c3Q6Fr1q0aFXOALa9PqF8d77H3c-9yDaEBif?purpose=fullsize
 
5

Fuel Oil

Fuel oil contains relatively large hydrocarbon molecules.

It has:

  • high boiling points
  • relatively high viscosity
  • low volatility

It has historically been used in applications such as:

  • large ships
  • industrial heating
  • some power-generation systems

Lubricating Oils

Even larger hydrocarbons can be found in lubricating fractions.

They tend to have:

  • high boiling points
  • high viscosity
  • low volatility
https://images.openai.com/static-rsc-4/8B02yMHo2Mx8QyjeTFQERa3r-tvTilp_6JZjf1bMMp_kLGHHLUulZcM1tydGk-fOam76HV2tOhQ4gNf0FvK77YrtW46wrHTKoqFuDKPizBhp3ADUqVqV3wvsMG7uvJqCqQ-hy5_mrNUf0cv5X_9N2fV3_wKvHDT7X8eXPit68jMf7Ncw0LkXSz20FmiqmZiL?purpose=fullsize
 
https://images.openai.com/static-rsc-4/7S5pHuLXG9bf8AA3b_thjsrVXoTsLysm_CtUDnw2YuoW__EzKHVYiMpvaeNlN7gTV9sAD1IRlV_M1SiOxxuuCFxArDRueIXTwbq_HD-yI3ZYbcx1LGwOHPS5eOdCDa53u1hHk2rMDjB5IwT81b0yO1dB6WEbAjZqWBtoQcXcVw8GRjTS3Uw2TdAkdUJu0Zrv?purpose=fullsize
 
https://images.openai.com/static-rsc-4/VY923PgaG_3Ktqn1i_rtEkutR3IA4WcAzYyu5-jyvWgYHHBp6mwWlEDjwi3gFJdPJ2Ivtq8ohWs6AnVyxM9kIHtA6CeO1Eo--wkwHT2N-l7c6DZpTx63iO-_TC48c7hbVTsYBBDcIKociqkN-3FKQT3ZgbiboizuBuRvl86rS7dZp9Uey36wq8OQoj6dnhoE?purpose=fullsize
 
5

These properties make them useful for reducing friction between moving surfaces.

A lubricant needs to remain between surfaces rather than evaporating quickly.


Waxes

Some long-chain hydrocarbons are solid or waxy at room temperature.

Paraffin wax is a familiar petroleum-derived material.

Uses can include:

  • candles
  • coatings
  • polishes
  • waterproofing
  • packaging applications

Longer chains have stronger intermolecular attractions, contributing to their higher melting and boiling temperatures.


Bitumen

At the bottom of the fractionating system is a very heavy residue containing very large hydrocarbon molecules and other heavy components.

One important product is:

bitumen

https://images.openai.com/static-rsc-4/gsM3V6cEmSEx5y3ZqKjqgZPNt593Hj2rOka7NVq9dryJQySZ3oMMl69V8iVak4cqSdRuvcH6SY6B8mvfzHqslJUlZebuYMx8wfl62E4JbwdSPDM4WGNTUiUWre1N0hKC3KGx_XQcWatnJQoQhFuTxj9rhj5fqTmG1oK4n4H3R-NnfwMKQn0yQP68hnspqobm?purpose=fullsize
 
https://images.openai.com/static-rsc-4/3YWLw1DxqqAXM7OmkEIvWyFrjl-18DbVJSVHJC0ZGn6RPv0Lzh_EBBbE1bWTStVaOVFHSpS4Ir8ZGvMpSIh6OLYqYJkoJqYvwlLql4I5sLXfzpJEhosfn5h7CcONYcuQmcaCq5cSA8xJ909n2QqdG4zYVQPxOczdEm7QXhWyKIDh9z_oIj8mHRUzK_QLMDTN?purpose=fullsize
 
https://images.openai.com/static-rsc-4/a0UodqQ7ZwjVadte8kMpucMnX66JA0SWMO3UFiFYDI8Rk__Vs9tH0gfEwpRDdpn7jgeox_wUxS9Swq0rVNl8pDIP2mQ5yfg69x7mzXlEBOVpdpVnL2CGTYBLFu5KJ1D00UfNDoPt1vn7e49seDOzRjTZSL29r6GNZDoK16DAtJRI8tNUu4M1nKXjtIVv11BV?purpose=fullsize
 
4

Bitumen is:

  • very viscous
  • very low in volatility
  • dark
  • thick
  • useful for road surfacing and roofing materials

Comparing the Top and Bottom of the Column

Near the top:

  • shorter hydrocarbon chains
  • smaller molecules
  • weaker intermolecular forces
  • lower boiling points
  • greater volatility
  • lower viscosity
  • easier vaporization

Near the bottom:

  • longer hydrocarbon chains
  • larger molecules
  • stronger intermolecular forces
  • higher boiling points
  • lower volatility
  • greater viscosity

This pattern is central to understanding petroleum fractions.


A Useful Trend

Moving from the top toward the bottom of a fractionating column:

Chain length ↑

Molecular size ↑

Boiling point ↑

Viscosity ↑

Volatility ↓

https://images.openai.com/static-rsc-4/kcj1URHLnywXZViJ8_UaLefl9Ppv5mUvPKZC_OzgkVrkCTQHu8miAJejWSGKolEv5M1rfqgjQfBobfqAxGaSqlZtqOOyhw2DR_PY_p9TQURpGzVYiyGyNewzKBubwIWkeFFrhYWcw8xf0DyEkpC1hRB1NeROHyqas_CHhQGxdx_I2i6M1oLXyO5ksFd1LMK8?purpose=fullsize
 
https://images.openai.com/static-rsc-4/hC69OL2SXdYSk0tJNJ_p4s15VoDIKh2bhX7bFeqY4OIuTH4SQwCGTwyZWCur808EiiXAOOiKWlBB10Zu0_lOWL0BzgJ2EO15DmpoBLBl_gG6mscsyTxj_OKentjYyAVHRuhk5Ou86jsBb3o-63ldpc5aL5pV7E_-qFN-KKd0l4CuvTaZmr_SbFjs9WpMIIU-?purpose=fullsize
 
https://images.openai.com/static-rsc-4/ghBSu1GES_jl5b_LurThEW19g-wRhyybZUfbyJgJjfkmtESsqWNvWul7mUd7TFVvraCfmnd_lbq56_YCP7pJvWyg2EjOZMTG8KDfBBgHuUcWqj9HPl2zeeNBSULT006tnjIo1RiOapvc3KjhPgLSG-NfTPHuYSVaP8ISXuoPyzXArEDP6-AcrxzQsG48lG6J?purpose=fullsize
 
6

Flammability and ease of ignition also generally decrease as the fractions become heavier, although actual combustion behavior depends on the specific fuel and conditions.


Why Long-Chain Hydrocarbons Have Higher Boiling Points

Long-chain hydrocarbons contain more electrons.

Their larger electron clouds are more polarizable.

Therefore, they experience stronger:

London dispersion forces

More energy is needed to overcome these intermolecular attractions.

Therefore:

boiling point increases

This gives the full explanation:

Longer chain

↓

Larger molecule

↓

More electrons and greater polarizability

↓

Stronger London dispersion forces

↓

More energy required to separate molecules

↓

Higher boiling point


Fractional Distillation Is a Physical Process

Fractional distillation does not normally convert one hydrocarbon into another.

It separates hydrocarbons according to differences in physical properties.

No new substance needs to be produced during the separation itself.

Therefore:

fractional distillation is a physical separation process

rather than a chemical reaction.

https://images.openai.com/static-rsc-4/-ICPaGVLqIaY2wTvV7-5WWRoAmzlZ3G312dpmYaiK6SGo8YgpYx4Fncobt7qUfi0dKru7vPEQz2SzZI8DcIGdEPcsVTuayOrNTggOV5nIUIs4R7d6UP9Kt3r68p4HSEpIeL49DjSB1_HOWwghqb79H1ldJZpg7AKdEnvoO7mjsCDdQj-kQYgxSQqkvVXmOXU?purpose=fullsize
 
https://images.openai.com/static-rsc-4/ccFjZd6ubOIbkgMMwFeKwy3niEKlPEx_FveFdIeMOJQPB3AH7HAKWCg0f7MZ13W-SUJ25-2E9624rODWjXXsoFtx7G5FnUIL-nuVt2FD0kzoNGbsOycAa65TQ8KaTP6Kt9HbdvNXO2ffYatSZCfqLUiCn91aDB7zNfLD0tnr2npCgdb5zjXVF4-dn04OzmvN?purpose=fullsize
 
https://images.openai.com/static-rsc-4/Yemp35xrj6DrrzhChOsslSbqSq95v9Jdo16QP0v47aPH1aqlIvcVbiCRXYQUOrY4XA4yWHQxuxCeF00R-70Fez9sNL6JwmPWrDy59X_en8APSgVuJM5D3KA7bMVn6D2mTloGHoFXbS-mNh5TribA3tfLYXGvYsho9EarjbBDgPpQCcSj_bqYc8A_xg1NTj_u?purpose=fullsize
 
5

The hydrocarbons repeatedly vaporize and condense as they move through different temperature regions of the column.


Distillation vs Fractional Distillation

Simple distillation can be useful for separating a liquid from dissolved substances or liquids whose boiling points are widely separated.

Fractional distillation is particularly useful when separating mixtures containing many liquids with different but sometimes relatively close boiling ranges.

Crude oil contains many hydrocarbons.

Therefore, a fractionating column is used to achieve much more effective separation.


Fractions Are Boiling Ranges

A petroleum fraction does not normally have one exact boiling point.

Instead, it has a:

boiling range

This is because a fraction contains several different hydrocarbon molecules.

For example, a fraction might contain hydrocarbons that boil across a particular range of temperatures.

Therefore:

fraction ≠ single pure hydrocarbon


Why Some Fractions Are More Useful Than Others

Demand for petroleum products is not equal.

Modern societies often require large quantities of:

  • transportation fuels
  • petrochemical feedstocks
  • aviation fuels
  • diesel

However, crude oil does not necessarily contain these fractions in exactly the proportions society wants.

This creates an important industrial problem.


Cracking

Large hydrocarbon molecules can be converted into smaller, more useful molecules through a process called:

cracking

https://images.openai.com/static-rsc-4/3q-FYaecdmTo31XlUg1LQ-Z-DrouNBOMXTTxkGvtvNnQMNRdwGEGHN6N50AFRo6rbt7-sf9tio5U2JBkFk9nYLsGyPoQDZEKqB2izxVboymhSYPgXG2FQM2xSHaDtya4iIqnZaftMG4hCs3OVXfiWzkRCOuKG1WN0iUr79PjB4Vt7y3T9LQ9ykeaS_cKtnhH?purpose=fullsize
 
https://images.openai.com/static-rsc-4/ww7xXxI1tnGRpymQjYw1BF5CuSLXA0szap-vvzAqJS3swDJmSw73THGOSqlAWAUaBiLMep3kqoKxr-8OUHpb_9xVh7l2nzO_XAplGmgDfOi-skTSMitpRKNwzKQ5gDP3lDuX0z8GYLBOLt7wmrk3jzTMUe7hKiJmXV17kA6qVwg9Eo2sw381xLHXygVrXkX3?purpose=fullsize
 
https://images.openai.com/static-rsc-4/YJ_Yy-lcum_rmI4H7Xommou4h0OwZ-K5o0_G1_1nP0efaXUDhYUDmi-XnYpeTlzs5HZrKdHR_CJH1asSwCoQtOm8F24GmgWZEviT_x8p-5fgQroQzkmtpxuM6lZaWV38qwcQ_Vi_CPwzejO09Rk3CEXEhGFXePVKIWFSPi1HjF-Og9ac2B2g5TpxQ8QzciUA?purpose=fullsize
 
6

Cracking can produce:

  • shorter alkanes
  • alkenes

Shorter hydrocarbons can be useful as fuels.

Alkenes are especially valuable as raw materials for making polymers and other chemicals.

Cracking is a chemical process, unlike fractional distillation.


Fractional Distillation vs Cracking

Fractional distillation:

separates existing molecules

Cracking:

changes molecules into different molecules

Fractional distillation is primarily:

physical

Cracking is:

chemical

This distinction is important.


Petroleum as a Fuel Source

A major use of petroleum is the production of fuels.

Petroleum-derived fuels are used in:

  • cars
  • trucks
  • aircraft
  • ships
  • machinery
  • heating
  • some electricity generation
https://images.openai.com/static-rsc-4/04qIwo_ZEjJugm4CPHT7MegggadyTw_KBKJryUcVCKO3AmdPmt1HKQemrGuuaYNA7MVT4RyO6JA4b2lHPCkL1p4bim-YilpOamXLDTX9wGDaIGxbbWiGdAUQhUu3F9zLZ_uk6Aba136VcKTbZlrZnMbJCRLAbo55hJKnIYoRdqiBkhsDPRKc52Ux0OBe5noE?purpose=fullsize
 
https://images.openai.com/static-rsc-4/f92zBmXM-Uo-w8pIsd6XF81zJX9o1TqZqL2NW-n0MUvqh3O8x0TDp7WFpCEUJvONVFyjvegmeeRjgP8_sqOj46zaGo5ICsOk5ySH24wSV7kY54UvKAwehJii_fgMIdUwI270zgFMVr7K_b6xKR00CtCOYL-O89YO6LMPjaquJYX21b2_GthK9RgDA8EIKq8m?purpose=fullsize
 
https://images.openai.com/static-rsc-4/UcyHLK_pKd9Yg9xYvZqPiH-ViYWlfHyPpmn-KiC5GqibQ-62vEzdYr52SmqfjIEGsKjJadxMBYWN2LPAnV8n-NQJR653IYAAyCiEpr8H1WVOrtB7d4iRHCJWJtyotMFAiYVcZRWAPac6Jd-QsEvMt_XULbOKAtMo2_muJXafvmxHraAUkht-BIJRQ_NvEf1n?purpose=fullsize
 
5

These fuels have high energy densities and have historically been convenient to store and transport.


Petroleum as a Chemical Feedstock

Petroleum is also extremely important as a raw material for the chemical industry.

Petrochemical feedstocks can be used to manufacture:

  • plastics
  • synthetic fibres
  • synthetic rubber
  • paints
  • detergents
  • solvents
  • adhesives
  • coatings
  • packaging
  • many industrial chemicals
https://images.openai.com/static-rsc-4/0fMKSK6uOxuJMJnPzC-h56QtA52s_BOyncc107eTbNOt9kw1YgEIN5y-pccGpewmWi7dvJqLjPlR4tnry_lS0ArahHoisoqh9q5ur6iCWnf4LIA4ETJKPKsz_6zW50ATa8UjTUJbpRHWtZpNnPe0sPVLvv70a8kFFR3cu4nybTDhePGfUmRmU-LsH_MJM_Fy?purpose=fullsize
 
https://images.openai.com/static-rsc-4/OfvtYdgFwG3UMaMZ4TV0pmqDKuyiwrONqfdq414Te8nvztztpClHrvkyQMoacN-vSaouPtEZeeZMGfBVT8_gRCbFl3Q3fZ33Ll6yd9B_tmbkub4bwYG-I7QTaco3nq676zCwo_Wwu7ZL3yL5C_9OFVacnS2NZZEV5KM2QlutLoy_jN4b4div8ba59j6_jgGG?purpose=fullsize
 
https://images.openai.com/static-rsc-4/nj5OWuxwqQTOp3FOipdpF4BlEwDrxLnI_AhvxQjbgklDyp0aRYfWYCu5LlGqQgZCKq0T38ZogJxR6EMf9CCmLAMyg5zAd4SOP_rNU5owzQ3pZCNrxdAyuZ0AW3ex2U4Bw1lTACm8oRn4-FHtFad3RcGxnI3bAW-LMHhXaUqxDz91s1iLfAklQtAaYuO9tVIV?purpose=fullsize
 
5

This means that petroleum affects everyday life far beyond transportation fuels.


Petroleum and Plastics

Many plastics begin with small organic molecules produced by processing petroleum fractions.

For example, cracking can produce alkenes such as ethene.

Ethene can then be used to make:

poly(ethene)

This creates a connection between:

crude oil → fractions → cracking → alkenes → polymers

Petroleum chemistry therefore provides important raw materials for the plastics industry.


Petroleum in Transportation

Different transportation systems require fuels with different physical properties.

Gasoline is suitable for many spark-ignition engines.

Diesel is suitable for compression-ignition engines.

Kerosene-type fuels are used in turbine-powered aircraft.

These fuels differ in properties such as:

  • volatility
  • boiling range
  • viscosity
  • ignition behaviour

Their molecular composition therefore affects their practical use.


Petroleum and Roads

Not every useful petroleum product is burned.

Bitumen is a major example.

https://images.openai.com/static-rsc-4/6CDasKq4dINjyuwwVksZF_sFQTKrb2eQBcedu6VNnMXwpsD70837EGUglbq3cdLmw7RQDZbnLzlP1Rj5nziwYrAbhw1hwkfcC8zG8uyaf_gFJS3YFqh11gJSivVijsyG4MyPPGATggWdYf0yoEL9bwS_M7V-VAZHkyT4mzZ_qy0E7YwAXCi-AlTlrj_7dxAQ?purpose=fullsize
 
https://images.openai.com/static-rsc-4/D9x0zI-v4pSZWww6RgO5nmrLq_NyMsioUT9B8pQ9QJjVZCyYmggr4ZINRFaT6hUTpNSwemRx5cvPtcEBEitKejBiE658Vg2pKb4gyVB1umdXbBJ5-l0Pq3_BVwaZGuczmbSyGm2AGIunED3DaiblwvwvBVaLcLUbU-pZwDF5cZ5uqo1ehf611WAqFUvQX3SI?purpose=fullsize
 
https://images.openai.com/static-rsc-4/Y-zWBblYQwqlQnEtaszsMkAc4KoL4AsS4knuSCztbkEPats7P0DxZI9hIlRFulVpRZ-fGekDmKPAYuz0FzorhGQcdqGsSZq-2Y_D6EWq-Sh4v4898mjTS2Q8aNhkpnZ2ZU_5L7KNfphytQz97hfDtRpmDTdJD9-UaV1PwkrpHogAQrKPTExBOHXMa4UiUBXw?purpose=fullsize
 
6

Its high viscosity and waterproof properties make it useful in:

  • roads
  • roofing
  • waterproof surfaces

This shows how physical properties determine applications.


Environmental Considerations

Petroleum products provide important materials and energy, but their production and use also have environmental consequences.

These include:

  • carbon dioxide emissions from combustion
  • air pollution from combustion
  • accidental oil spills
  • habitat disruption associated with extraction and infrastructure
  • plastic waste
  • greenhouse-gas emissions across production and use
  • dependence on a finite resource
https://images.openai.com/static-rsc-4/CQk7mQWI8wYNOUEaUwq6_H7M_8H_Uyf7oSGqjcIwPrHdpAeaGsHWYydqKIZWB9WHrzgZtwBMFQT9z0_Ig4UFo5rkN9w2j8rK3SF4x2iTs0RjYb8Y6vizQvNb_bpyXIQTu4aaiP14emPJaE9L0jNHRF2S7kUJqu8Pn14aoS5TioeSKNbT0M816btbQKU93Wj6?purpose=fullsize
 
https://images.openai.com/static-rsc-4/-6zL5bno6Cg1NRXxA3474oa2feCI3uFpoQ81MyczwbqgyONv36k2D416jtu8YVcj7meRMwFJfzWfwkb0w73d8T6Pd5VY4Ph5KpuRvxgjfSRNWzCsYL8yDCjTUDo_ueSv_rMmwkpgaroqjI8f9-LxHOoaTBZhdGSogMQHuZ6Oi3t_2S_HAlUcoMiXWvpiv7gy?purpose=fullsize
 
https://images.openai.com/static-rsc-4/MVSxohbOdg4tUVcZqOZsD1jLYeUfSJWeKJ3jYZ-pI6WX0LD44N2taH6qe-4d7yR3_nJTRneCyGGseiSEQJPhtr71EokYaZidsz82uXt-W0tM5c7gqGFMdoPEvagQyJL-gX6gFl5-l1Y4IQ_g3Yzl8bV5Ne6srytQfiqgHf4qKz3jy2pUzSoGGV30iQ-k1DXu?purpose=fullsize
 
5

Understanding petroleum therefore involves considering both its usefulness and its environmental impacts.


Petroleum Is Non-Renewable

Crude oil takes millions of years to form naturally.

Humans consume petroleum far faster than geological processes replace it.

Therefore, crude oil is classified as:

non-renewable

This does not mean that petroleum will suddenly disappear at a particular moment.

It means that it is a finite geological resource that is not replenished on a human timescale.


Worked Example 1: Identifying a Mixture

A student says:

"Crude oil is one giant hydrocarbon molecule."

Is this correct?

No.

Crude oil is a:

mixture of many different hydrocarbons and other compounds.


Worked Example 2: Predicting Boiling Point

Which would generally have the higher boiling point?

C₅H₁₂

or:

C₁₂H₂₆

Answer:

C₁₂H₂₆

It is larger and contains more electrons.

Therefore, it experiences stronger London dispersion forces.

More energy is required to separate its molecules.


Worked Example 3: Position in the Column

Which would generally condense higher in a fractionating column?

A short-chain hydrocarbon or a long-chain hydrocarbon?

Short-chain hydrocarbon

It has a lower boiling point and must reach a cooler region before it condenses.


Worked Example 4: Heavy Fraction

A petroleum fraction is:

  • very viscous
  • not very volatile
  • composed mainly of large hydrocarbon molecules

Where would you expect it to be collected?

Near the bottom of the fractionating system.

Its large molecules have high boiling points.


Worked Example 5: Light Fraction

A fraction contains small hydrocarbons with low boiling points.

Predict two properties.

It will generally have:

high volatility

and:

low viscosity

It would be collected relatively high in the column.


Worked Example 6: Gasoline vs Fuel Oil

Which fraction generally contains shorter hydrocarbons?

Gasoline

Which generally has the higher boiling range?

Fuel oil

Which is generally more viscous?

Fuel oil

Which is generally more volatile?

Gasoline


Worked Example 7: Fractional Distillation

Why do different hydrocarbons condense at different heights?

Because they have:

different boiling points

The column has a:

temperature gradient

so different hydrocarbons condense where the temperature falls below the range at which they remain vaporized.


Worked Example 8: Physical or Chemical?

Is fractional distillation a chemical reaction?

No.

It separates substances according to physical properties.

The molecules are not converted into different substances simply by the distillation process.


Worked Example 9: Petroleum Product

Which fraction would be most closely associated with road surfacing?

Bitumen

Bitumen consists of very heavy material remaining near the bottom of petroleum processing.


Worked Example 10: Explaining a Trend

A student writes:

"Long hydrocarbons boil at higher temperatures because they have stronger covalent bonds."

This is not the correct explanation.

The important difference during boiling is:

intermolecular forces

Longer hydrocarbons have larger, more polarizable electron clouds.

Therefore, they experience stronger London dispersion forces.

More energy is required to separate the molecules.

Therefore:

their boiling points are generally higher.


Reading a Fractionating Column Diagram

When interpreting a fractional distillation diagram, remember:

Top of column

Cooler

Shorter chains

Lower boiling points

More volatile

Less viscous

↓

Middle

Intermediate properties

↓

Bottom of column

Hotter

Longer chains

Higher boiling points

Less volatile

More viscous

https://images.openai.com/static-rsc-4/xUYpkxYD7tMhJ5E_RQp6-N1YbOPfuZ4NCBdl39E9T9fHxXW199n5tjyDdy-y6pNTFFQaJQtmZxv_ARPOvO32z36gof2UtW68iLwLk4_-qkrvYPeIz1k8cQHBePTk9yQvQHe-J7a7VYyO6nqh4j0RoHo9lX5xtmoVscknEzDVXdS76DIp4fsWRXnv8foiLpW4?purpose=fullsize
 
https://images.openai.com/static-rsc-4/hC69OL2SXdYSk0tJNJ_p4s15VoDIKh2bhX7bFeqY4OIuTH4SQwCGTwyZWCur808EiiXAOOiKWlBB10Zu0_lOWL0BzgJ2EO15DmpoBLBl_gG6mscsyTxj_OKentjYyAVHRuhk5Ou86jsBb3o-63ldpc5aL5pV7E_-qFN-KKd0l4CuvTaZmr_SbFjs9WpMIIU-?purpose=fullsize
 
https://images.openai.com/static-rsc-4/7KcnRE5vnjJ8MwFOwS4CZqQ66cxUj37Ay3LNf1_jyTrDElVfaHH1SLzSUhWCAYY0mDJn7PA6jk6qk-eIHlHdIcUAmQwo7zZ9h9rBOkFNICYXm6O4UXfCO30JjqtlAnnd6nU0R4ofWCM5vu1jy52zXCkOkMr10H1OCKTSsL9jSqSm8Mgtlxx6jXVXQ-TL0Cf3?purpose=fullsize
 
6

A Reliable Fractional Distillation Explanation

If asked to explain fractional distillation, a strong answer could follow this sequence:

1. Crude oil is heated.

2. Most hydrocarbons vaporize.

3. The vapours enter a fractionating column.

4. The column is hot at the bottom and cooler toward the top.

5. Hydrocarbon vapours rise and cool.

6. Different hydrocarbons have different boiling points.

7. They condense at different heights.

8. Hydrocarbons with similar boiling ranges are collected together as fractions.

This explains both the process and the scientific reason it works.


Common Mistakes

Mistake 1: Saying crude oil is a pure substance

Crude oil is a:

mixture


Mistake 2: Saying crude oil contains only alkanes

Crude oil contains many hydrocarbons, including but not limited to alkanes, as well as smaller amounts of other compounds.


Mistake 3: Saying fractional distillation creates hydrocarbons

Fractional distillation:

separates hydrocarbons already present in the mixture.


Mistake 4: Saying the column is hottest at the top

The fractionating column is:

hotter at the bottom

and:

cooler toward the top


Mistake 5: Saying long-chain hydrocarbons have lower boiling points

The general trend is:

longer chain → higher boiling point


Mistake 6: Saying fractions are pure substances

Each fraction normally contains:

a mixture of hydrocarbons with similar boiling ranges.


Mistake 7: Confusing fractional distillation and cracking

Fractional distillation:

separates molecules

Cracking:

breaks large molecules into smaller molecules


Mistake 8: Saying boiling breaks C–C bonds

Boiling primarily overcomes:

intermolecular forces

It does not normally break the covalent bonds within hydrocarbon molecules.


Did You Know?

A modern oil refinery does much more than simply separate crude oil.

https://images.openai.com/static-rsc-4/BQOldHsJ88Fmzq-ueYixagAQMsoaYPia-aU7VyZ0OHdUItOGM4Uyqp_iyZ56JU71zPHtRbcwL5aoDz-tw6H6k3dsc6AvE8uxRfKw-_M4i2Rgyz4_SbKYIh_Eu5SlnJO3oE5ToM45z51ZCpygkHYwXd8g2nRcu2bjUK-iRyzYN_kQnNWVMatZ9WiVQIZ-9ZeL?purpose=fullsize
 
https://images.openai.com/static-rsc-4/S7X9BulpeAYOi95IltRg-j7K_Fe0IcgL8FKySFVDaisDOioJDHKHsm97DHHgoGR_r7jBDHfl-vuCNrWFqAywnKeQ3I58zRe0_KRDarOr2GpEct-r1rL1MEd7fMdjm8PO55t_rWnbtDtlMDlrFXDkSwhkLWWouPnhNQyOtrHekNjAdtGa1DmVKDcMpSlpsfzR?purpose=fullsize
 
https://images.openai.com/static-rsc-4/vekX46tmc5s7fSgSnjfkGn9lcohteFVwkwWRTBNr83FS_XlA72fJRasGsaJqKxyWfporbop-XceQQQH_04EVoY5tIOKL9yqR0CP9nzIOBTRvZUzA9e5Ph32p7LzF0odbQuSxqAE5beZXyxT0pCmVYJAsmpqLEmTDCWgKA5bcH79v3IyzKFSybDferPQ42ECj?purpose=fullsize
 
5

After fractional distillation, fractions may undergo additional processes to change their composition or improve their usefulness.

These processes can include:

  • cracking
  • reforming
  • removal of sulfur compounds
  • blending
  • purification

The refinery therefore combines physical separation with chemical processing to produce materials with particular properties.


Key Terms

  • Crude oil: Naturally occurring mixture containing many hydrocarbons and smaller amounts of other compounds.
  • Hydrocarbon: Compound containing only carbon and hydrogen.
  • Petroleum: Naturally occurring hydrocarbon mixture and the products derived from it.
  • Fraction: Mixture of hydrocarbons with a similar range of boiling points.
  • Fractional distillation: Separation of a liquid mixture using differences in boiling points.
  • Fractionating column: Industrial column in which hydrocarbon vapours separate according to boiling range.
  • Boiling point: Temperature at which a liquid boils at a specified pressure.
  • Vaporization: Physical change from liquid to gas.
  • Condensation: Physical change from gas to liquid.
  • Volatility: Tendency of a substance to vaporize.
  • Viscosity: Resistance of a fluid to flowing.
  • London dispersion force: Intermolecular attraction important between hydrocarbon molecules.
  • Refinery gas: Light hydrocarbon fraction containing very small molecules.
  • Naphtha: Petroleum fraction commonly used as a petrochemical feedstock.
  • Kerosene: Petroleum fraction used particularly in aviation turbine fuels.
  • Diesel: Petroleum-derived fuel used in compression-ignition engines.
  • Bitumen: Heavy petroleum material used in applications such as road surfacing and roofing.
  • Feedstock: Raw material used to manufacture other chemicals.
  • Cracking: Chemical process that converts larger hydrocarbons into smaller molecules.
  • Non-renewable resource: Resource that is not replenished on a human timescale.

Key Relationships

Moving up the fractionating column:

Temperature ↓

Average chain length ↓

Boiling point ↓

Viscosity ↓

Volatility ↑

Moving down the column:

Temperature ↑

Average chain length ↑

Boiling point ↑

Viscosity ↑

Volatility ↓


Key Takeaways

  • Crude oil is a mixture, not a pure substance.
  • Most compounds in crude oil are hydrocarbons.
  • Hydrocarbons contain only carbon and hydrogen.
  • Crude oil contains molecules with many different carbon-chain lengths and boiling points.
  • Crude oil is separated into useful fractions using fractional distillation.
  • The fractionating column is hot at the bottom and cooler toward the top.
  • Crude oil is heated so that much of it vaporizes before entering the column.
  • Hydrocarbon vapours rise through the column and cool.
  • Different hydrocarbons condense at different heights because they have different boiling points.
  • Fractions contain mixtures of hydrocarbons with similar boiling ranges.
  • Short-chain hydrocarbons generally have lower boiling points, lower viscosity, and greater volatility.
  • Long-chain hydrocarbons generally have higher boiling points, greater viscosity, and lower volatility.
  • The increase in boiling point with chain length is explained by stronger London dispersion forces between larger molecules.
  • Important petroleum fractions include refinery gases, gasoline, naphtha, kerosene, diesel, fuel oil, lubricating materials, waxes, and heavy residues such as bitumen.
  • Fractional distillation is a physical separation process.
  • Cracking is different because it is a chemical process that converts large hydrocarbons into smaller molecules.
  • Petroleum is important not only as a source of fuels but also as a source of chemical feedstocks used to manufacture plastics and many other materials.
  • Petroleum products have played a major role in transportation, industry, construction, manufacturing, and modern chemical production.
  • Crude oil is a non-renewable resource, and its extraction, processing, use, and disposal can have significant environmental impacts.