Naming of Organic Compounds (Cambridge (CIE) A Level Chemistry): Revision Note

Exam code: 9701

Philippa Platt

Last updated

Nomenclature of Aliphatic Compounds

  • Systematic nomenclature can be used to name organic compounds and therefore make it easier to refer to them

  • The alkanes provide the basis of the naming system and the stem of each name indicates how many carbon atoms are in the longest chain in one molecule of the compound

Nomenclature of organic compounds table

Number of C atoms

Molecular formula of straight-chain alkane

Name of alkane

Stem used in naming

1

CH4

methane

meth-

2

C2H6

ethane

eth-

3

C3H8

propane

prop-

4

C4H10

butane

but-

5

C5H12

pentane

pent-

6

C6H14

hexane

hex-

7

C7H16

heptane

hept-

8

C8H18

octane

oct-

9

C9H20

nonane

non-

10

C10H22

decane

dec-

Side chains

  • When naming compounds with side chains or functional groups, number the carbon atoms in the longest chain, starting from the end that gives the lowest possible numbers to the substituents

  • In structural formulas, a side chain is often shown in brackets.

    • E.g. CH3CH(CH3)CH2CH3

  • Side chains are named by changing the -ane ending of the parent alkane to -yl

  • These groups are known as alkyl groups

Naming organic compounds with one alkyl side chain

Structural formula of 3-methyl hexane with numbering from left to right and right to left; correct naming identified as 3-methyl hexane.
The longest chain provides the main name and the side chain is shown as a numbered alkyl prefix
  • If there are more than one of the same alkyl side chain or functional groups, di- (for two), tri- (for three) or tetra- (for four) is added in front of its name

  • The adjacent numbers have a comma between them

  • Numbers are separated from words by a hyphen

Naming organic compounds with multiple, identical side chains

Diagram of 3,3,4-trimethyl hexane, showing the longest carbon chain and methyl group placements on carbons 3 and 4.
The longest chain still provides the main name and the side chains are shown as numbered alkyl prefixes
  • If there is more than one type of alkyl side chain, the same numbering system applies but the different side chains are listed in alphabetic order

Naming organic compounds with multiple, different side chains

Structural formula of 4-ethyl-2-methylhexane with highlighted longest chain and branches. Ethyl on carbon 4, methyl on carbon 2.
The longest chain still provides the main name and the side chains are still shown as numbered alkyl prefixes but in alphabetical order

Functional groups & their nomenclature table

Class

IUAC prefix–
or –suffix 

Example

alkane

–ane

ethane-structural-formula

ethane

alkene

–ene

ethene-structural-formula

ethene

halogenoalkane

fluoro–
chloro–
bromo–
iodo–

halogenoethane-structural-formula

if X = F, fluoroethane

alcohol

hydroxy–
–ol

ethanol-structural-formula

ethanol

aldehyde

–al

ethanal-structural-formula

ethanal

ketone

–one

propanone-structural-formula

propanone

carboxylic acid

–oic acid

ethanoic-acid-structural-formula

ethanoic acid

ester

–oate

methyl-ethanoate-structural-formula

methyl ethanoate

amine

–amine

ethanamine-structural-formula

ethanamine

nitrile

-nitrile

Nitrogen Compounds Nitriles, downloadable AS & A Level Chemistry revision notes

ethanenitrile

Worked Example

Name the following molecules using correct systematic nomenclature:

  1.  

    255-trimethylhex-2-ene
  2.    

    propanal
  3.  

    2-methylbutanal
  4.  

    butanoic-acid
  5. 2-chlorobutane

Answers:

  1. The chemical name is 2,5,5-trimethylhex-2-ene

    • The longest carbon chain is six carbons long

    • There is an alkene / double carbon-carbon bond on carbon-2

    • There are 3 methyl groups on carbons 2, 5 and 5

  2. The chemical name is propanal

    • The longest carbon chain is 3 carbons long with only single carbon-carbon bonds

    • There is an aldehyde group which is fixed as carbon-1

  3. The chemical name is 2-methylbutanal

    • The longest carbon chain is 4 carbons long with only single carbon-carbon bonds

    • There is a methyl group on carbon-2

    • There is an aldehyde group which is fixed as carbon-1

  4. The chemical name is butanoic acid

    • The longest carbon chain is 4 carbons long with only single carbon-carbon bonds

    • There is a carboxylic acid group which is fixed as carbon-1

  5. The chemical name is 2-chlorobutane

    • The longest carbon chain is 4 carbons long with only single carbon-carbon bonds

    • There is a chlorine atom attached to carbon-2

Examiner Tips and Tricks

An aliphatic compound is straight or branched-chain and also includes cyclic organic compounds that do not contain a benzene ring.

You've read 0 of your 5 free revision notes this week

Unlock more, it's free!

Join the 100,000+ Students that ❤️ Save My Exams

the (exam) results speak for themselves:

Philippa Platt

Author: Philippa Platt

Expertise: Chemistry Content Creator

Philippa has worked as a GCSE and A level chemistry teacher and tutor for over thirteen years. She studied chemistry and sport science at Loughborough University graduating in 2007 having also completed her PGCE in science. Throughout her time as a teacher she was incharge of a boarding house for five years and coached many teams in a variety of sports. When not producing resources with the chemistry team, Philippa enjoys being active outside with her young family and is a very keen gardener