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Functional Groups in the Cambridge Table

A concise Cambridge International AS Level Chemistry revision guide to the full table of functional groups (13.1.3).

It covers the classes not met on the individual naming pages, how each group dictates the properties of its compounds, and the extra naming rules for esters and nitriles (13.1.5).

AS Level
Topic 13: An Introduction to AS Level Organic Chemistry
9701 Papers 1 and 2
Cambridge International specification2 spec points in this lesson
  • 13.1.3
  • 13.1.5
What these spec points say
  • 13.1.3 understand that the compounds in the table on pages 29 and 30 contain a functional group which dictates their physical and chemical properties
  • 13.1.5 understand and use systematic nomenclature of simple aliphatic organic molecules with functional groups detailed in the table on pages 29 and 30, up to six carbon atoms (six plus six for esters, straight chains only for esters and nitriles)
Before you start

GCSE Recap: Homologous Series and the Groups You Know

Before you start, check the groups you can already recognise and why members of one series behave alike.

1

The Cambridge Functional-Group Table

Cambridge 13.1.3 states that the compounds in the syllabus table contain a functional group which dictates their physical and chemical properties, and 13.1.4 asks you to interpret and use the general, structural, displayed and skeletal formulae of every class in that table.

The individual naming pages cover alkenes, halogenoalkanes, alcohols, aldehydes, ketones, carboxylic acids and esters. This page completes the table.

ClassFunctional groupGeneral formulaNamingExample
AlkaneNone (C-C and C-H only)CnH2n+2Suffix -anePropane, CH3CH2CH3
AlkeneC=CCnH2nSuffix -eneBut-1-ene
HalogenoalkaneC-X (X = F, Cl, Br, I)CnH2n+1XPrefix fluoro-, chloro-, bromo-, iodo-2-Bromopropane
AlcoholC-OHCnH2n+1OHSuffix -olPropan-2-ol
AldehydeCHOCnH2nOSuffix -alButanal
KetoneC=O (within the chain)CnH2nOSuffix -onePentan-3-one
Carboxylic acidCOOHCnH2n+1COOHSuffix -oic acidPropanoic acid
EsterCOORRCOOR′Alkyl + -oateEthyl propanoate
AmineNH2CnH2n+1NH2Suffix -amine (or prefix amino-)Propylamine
NitrileC≡NCnH2n+1CNSuffix -nitrilePropanenitrile
AmideCONH2CnH2n+1CONH2Suffix -amideEthanamide
Acyl chlorideCOClCnH2n+1COClSuffix -oyl chloridePropanoyl chloride
HydroxynitrileC(OH)CN–Prefix hydroxy- with suffix -nitrile2-Hydroxypropanenitrile
AreneBenzene ring, C6H5–C6H5RNamed as benzene derivativesMethylbenzene

Key idea: The functional group decides the chemistry: every compound in a class undergoes the same characteristic reactions, which is why Cambridge asks you to recognise each group from a formula and to name compounds from it.

Each class is recognised by its functional group and named with its own suffix or prefix.

Check your understanding

Quick Check: Name the Class from the Formula

Drag a class name into each gap; one compound needs two of them.

2

The Nitrogen-Containing Groups

Four of the classes contain nitrogen. They are met in Topic 19 (nitrogen compounds) and in the synthesis routes of Topic 21, but you must recognise and name them from Topic 13 onwards.

ClassWhat to look forNaming ruleWatch out
AmineAn NH2 group on a carbon chainName the alkyl group then add -amine: ethylamine, butylamineNot to be confused with an amide, which has C=O next to the nitrogen
AmideCONH2: a carbonyl carbon bonded to NH2Replace -oic acid with -amide: propanoic acid gives propanamideThe carbonyl carbon is counted in the chain
NitrileC≡N at the end of a chainCount the nitrile carbon in the chain and add -nitrile: CH3CH2CN is propanenitrile, not ethanenitrileCambridge restricts nitrile naming to straight chains
HydroxynitrileOH and CN on the same carbonNumber from the nitrile carbon: CH3CH(OH)CN is 2-hydroxypropanenitrileFormed when HCN adds to an aldehyde or ketone

Exam focus: The nitrile carbon is part of the chain. CH3CN has two carbon atoms and is ethanenitrile; CH3CH2CH2CN has four and is butanenitrile.

Look next to the nitrogen: C=O makes an amide, C≡N a nitrile, and neither an amine.

Check your understanding

Quick Check: The Nitrogen Classes

Five quick questions on compounds the page has not used; classify first, then name.

3

Acyl Chlorides and Arenes

Acyl chlorides contain the COCl group: a carbonyl carbon bonded to chlorine.

They are named from the parent acid by replacing -oic acid with -oyl chloride, so CH3COCl is ethanoyl chloride and CH3CH2COCl is propanoyl chloride.

They are very reactive derivatives of carboxylic acids and appear in Topic 18.

Arenes contain a benzene ring, C6H6, drawn as a hexagon with a circle to show the delocalised electrons.

Substituted arenes are named as derivatives of benzene: methylbenzene, C6H5CH3, and chlorobenzene, C6H5Cl.

When the benzene ring is a substituent on a chain it is called a phenyl group, as in phenylethene.

Arenes are studied in detail at A Level (Topic 30), but their formulae appear in AS questions on functional groups.

Key idea: A benzene ring is unsaturated, but it does not undergo the addition reactions of alkenes; its stability comes from the delocalised electrons.

Check your understanding

Quick Check: A Ring and a Double Bond in One Molecule

Decide which part of phenylethene reacts with bromine, and why the other does not.

4

Naming Esters: Six Plus Six

Cambridge 13.1.5 allows ester names with up to six carbon atoms in each part. An ester is named in two words: the alkyl group from the alcohol first, then the acid part with -oate.

  1. Find the C=O carbon. The chain it belongs to came from the acid and gives the second word: methanoate, ethanoate, propanoate, butanoate, pentanoate, hexanoate.
  2. The alkyl group on the single-bonded oxygen came from the alcohol and gives the first word: methyl, ethyl, propyl, butyl, pentyl, hexyl.
EsterAlcohol part (first word)Acid part (second word)Structural formula
Propyl ethanoatePropyl, from propan-1-olEthanoate, from ethanoic acidCH3COOCH2CH2CH3
Methyl butanoateMethyl, from methanolButanoate, from butanoic acidCH3CH2CH2COOCH3
Hexyl hexanoateHexyl, from hexan-1-olHexanoate, from hexanoic acidCH3(CH2)4COO(CH2)5CH3

Exam focus: Write the formula the way the name reads, acid part first with its C=O: CH3CH2COOCH3 is methyl propanoate. Students often swap the two parts.

Check your understanding

Quick Check: Name Four New Esters

Work out both words of each name, then type it in.

Check your understanding

Quick Check: Pick the Accurate Statement

In each round, choose the one statement that reads the formula correctly.

5

Common Exam Mistakes

  • Naming CH3CH2CN as ethanenitrile. The nitrile carbon counts, so it is propanenitrile.
  • Confusing amines (C-NH2) with amides (C(=O)NH2). Look for the carbonyl group next to the nitrogen.
  • Swapping the two parts of an ester name, or writing the alkyl group on the wrong oxygen.
  • Treating a benzene ring as an alkene and predicting addition reactions.
  • Giving a general formula for a hydroxynitrile: the syllabus expects the group C(OH)CN to be recognised, not a general formula.

Exam sentence: Each class in the Cambridge table is defined by its functional group; the group is named by a suffix or prefix, and the nitrile and carbonyl carbons are counted as part of the chain.

FAQs

These questions cover the functional groups students most often confuse.

How do I tell an amine from an amide?

Look at the carbon next to the nitrogen. In an amide it is a C=O carbon, CONH2. In an amine the nitrogen is bonded to an ordinary carbon, C-NH2.

Why is CH3CH2CN propanenitrile and not ethanenitrile?

The nitrile carbon is counted in the chain. There are three carbon atoms in total, so the stem is propane.

Does benzene react like an alkene?

No. Its delocalised electrons make the ring stable, so it does not decolourise bromine water by addition.

Which part of an ester name contains the C=O carbon?

The second word, the -oate part, which comes from the acid. The first word is the alkyl group on the single-bonded oxygen.

How is an acyl chloride named?

Replace -oic acid in the parent acid with -oyl chloride. CH3COCl comes from ethanoic acid, so it is ethanoyl chloride.

Dr. Mohammed Al-Fatah

Written by: Dr. Mohammed Al-Fatah

Chemistry specialist revision notes for A Level Chemistry.

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Copyright notice: This OLS revision content, including the explanations, layout, diagrams, tables and embedded learning structure, is authored for Online Learning System by Dr. Mohammed Al-Fatah. It may not be copied, reproduced, redistributed or adapted without written permission.