Nomenclature & Classification (Edexcel International AS Chemistry): Revision Note

Exam code: XCH11

Stewart Hird

Written by: Stewart Hird

Reviewed by: Caroline Carroll

Updated on

IUPAC Nomenclature

  • 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-

  • If there are any side-chains or functional groups present, then the position of these groups is indicated by numbering the carbon atoms in the longest chain starting at the end that gives the lowest possible numbers in the name

  • The hydrocarbon side-chain is shown in brackets in the structural formula

   CH3CH(CH3)CH2CH3

  • The side-chain is named by adding ‘-yl’ to the normal alkane stem

  • This type of group is called an alkyl group

Skeletal view of 3-methylhexane: the longest chain of six carbons numbered from the end that gives the lowest number, giving 3-methylhexane rather than 4-methylhexane

Naming Side Chains

  • 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

3,3,4-trimethylhexane showing two methyl groups on carbon 3 and one methyl group on carbon 4 of a six-carbon chain

Naming Multiple Side Chains

  • If there is more than one type of alkyl side-chain, they are listed in alphabetic order

4-ethyl-2-methylhexane showing a methyl group on carbon 2 and an ethyl group on carbon 4 of a six-carbon chain, listed in alphabetical order

Naming Side Chains in Alphabetical Order

Functional Groups & their Nomenclature Table

Functional group

Nomenclature

Alkene

-ene

Example: ethene

Displayed formula of ethene, H2C=CH2

Halogenoalkane

bromo-

chloro-

fluoro-

iodo-

Example: chloroethane

Displayed formula of chloroethane, CH3CH2Cl

Alcohol

-ol

Example: ethanol

Displayed formula of ethanol, CH3CH2OH

Aldehyde

-al

Example: ethanal

Displayed formula of ethanal, CH3CHO

Ketone

-one

Example: propanone

Displayed formula of propanone, CH3COCH3

Carboxylic acid

-oic acid

Example: ethanoic acid

Displayed formula of ethanoic acid, CH3COOH

Ester

alkyl -oate

Example: propyl ethanoate

Displayed formula of propyl ethanoate, CH3COOCH2CH2CH3

Amine

alkyl -amine

Example: ethylamine

Displayed formula of ethylamine, CH3CH2NH2

Nitrile

-nitrile

Example: ethanenitrile

Displayed formula of ethanenitrile, CH3CN

Worked Example

Naming organic molecules Name the following molecules using correct systematic nomenclature: 

Six skeletal formulae, numbered 1 to 6, to be named: two alkenes, two aldehydes, a carboxylic acid and a chloroalkane

Answer 1:

  • 2,5,5-trimethylhex-2-ene

    • The longest carbon chain is 6 carbons = hex

    • There is an alkene group which is a higher priority group than the methyl side chains

      • So, the carbons are numbered to make the alkene have the lowest possible number = -2-ene

    • This means that the methyl groups are on carbons 2, 5 and 5 = 2,5,5-trimethyl

Answer 2:

  • 2-propylpent-1-ene

    • The longest carbon chain that contains the C=C double bond is 5 carbons = pent

    • The double bond starts on carbon 1 = -1-ene

    • There is a propyl side chain on carbon 2 = 2-propyl

    • Note: the longest chain overall has 7 carbons, but the main chain must contain the C=C double bond, so the name is based on pentene, not heptane

Answer 3:

  • Propanal

    • The longest carbon chain is 3 carbons = prop

    • There is an aldehyde group = al

      • By convention, the aldehyde group is attached to carbon-1

    • The bonds within the main chain are all single bonds = an

Answer 4:

  • 3-methylbutanal

    • The longest carbon chain is 4 carbons = but

    • There is an aldehyde group = al

      • By convention, the aldehyde group is attached to carbon-1

    • The bonds within the main chain are all single bonds = an

    • There is a methyl side chain attached to carbon-3 = 3-methyl 

Answer 5:

  • Butanoic acid

    • The longest carbon chain is 4 carbons = but

    • There is a carboxylic acid group = -oic acid

      • By convention, the carboxylic acid is attached to carbon-1

    • The bonds within the main chain are all single bonds = an

Answer 6:

  • 2-chlorobutane

    • The longest carbon chain is 4 carbons = but

    • The bonds within the main chain are all single bonds = an

    • There is a chlorine atom attached to carbon-2 = 2-chloro

Reaction Classification

  • We can classify reactions into different types

    • An addition reaction is an organic reaction in which two (or more) molecules combine to give a single product with no other products

    • A substitution reaction is a reaction that involves replacing an atom or group of atoms by another

    • An elimination reaction is a reaction in which a small molecule (such as H2O or HCl) is removed from an organic molecule

    • A hydrolysis reaction is a reaction in which a compound is broken down by water (it can also refer to the breakdown of a substance by dilute acids or alkali)

    • A condensation reaction is a reaction in which two organic molecules join together and in the process eliminate small molecules (such as H2O or HCl)

      • Condensation reactions are covered at A level, in Units 4 and 5

Examples of an addition reaction (ethene and hydrogen forming ethane), a substitution reaction (bromine replaced by chlorine in 2-bromo-2-methylpropane) and an elimination reaction (ethanol losing water to form ethene)

The different types of reactions in organic chemistry

Oxidation & reduction

  • An oxidation reaction is a reaction in which oxygen is added, electrons are removed or the oxidation number of a substance is increased

    • In organic chemistry it often refers to the addition of oxygen or removal of hydrogen atoms to a substance

    • In equations for organic redox reactions, the symbol [O] can be used to represent one atom of oxygen from an oxidising agent

  • A reduction reaction is a reaction in which oxygen is removed, electrons are added or the oxidation number of a substance is decreased

    • In organic chemistry it often refers to the removal of oxygen or addition of hydrogen atoms to a substance

    • In equations for organic redox reactions, the symbol [H] can be used to represent one atom of hydrogen from a reducing agent

Oxidation of ethanol to ethanal using [O] and water, and reduction of ethanal to ethanol using 2[H]

In organic chemistry oxidation is often the gain of oxygen or loss of hydrogen atoms and reduction is the gain of hydrogen and loss of oxygen atoms

Polymerisation

  • In the AS level course all the polymerisation reactions covered are examples of addition polymerisation

  • Addition polymerisation is the reaction in which many monomers containing at least one C-C double bond form long chains of polymers as the only product

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Stewart Hird

Author: Stewart Hird

Expertise: Chemistry Content Creator

Stewart has been an enthusiastic GCSE, IGCSE, A Level and IB teacher for more than 30 years in the UK as well as overseas, and has also been an examiner for IB and A Level. As a long-standing Head of Science, Stewart brings a wealth of experience to creating Topic Questions and revision materials for Save My Exams. Stewart specialises in Chemistry, but has also taught Physics and Environmental Systems and Societies.

Caroline Carroll

Reviewer: Caroline Carroll

Expertise: Head of Content Delivery

Caroline graduated from the University of Nottingham with a degree in Chemistry and Molecular Physics. She spent several years working as an Industrial Chemist in the automotive industry before retraining to teach. Caroline has over 12 years of experience teaching GCSE and A-level chemistry and physics. She is passionate about delivering high-quality resources to help students achieve their full potential.