A functional group is an atom or combination of atoms which gives an organic molecule its

distinctive and characteristic chemistry. The term 'functional' group is linked to the concept of
a homologous series. A homologous series is a group of molecules with the same general formula
and the same functional group. They have similar physical and chemical properties (albeit with
trends e.g. increasing boiling point with increasing carbon chain length). The terms higher/lower
refer to a larger/smaller carbon chain.

* molecular formula e.g. C3H6O2, gives a summary of all the atoms in the molecule, but gives no
information on structure.

structural formula - minimal/abbreviated/shortened e.g. or but

unambiguous and no/some individual bonds are shown.

structural formula - full/displayed/graphical e.g. where all the

individual bonds are shown.

structural formula - full 3D spatial representation e.g. which shows the shape
of the molecule.

skeletal formula e.g. in which no H atoms bonded to carbon atoms are shown, the lines
represent either carbon-carbon bonds (single, double or triple), but other lines are needed to show
bonds to other atoms which are NOT carbon or hydrogen e.g. C-Cl in and hydrogen atoms are

shown if they are bonded to non-carbon atoms e.g. the -OH in .

FUNCTIONAL GROUPS and HOMOLOGOUS SERIES

nomenclature, structure and representation in pictures-graphics

ALKANES or cycloalkanes HYDROCARBONS (saturated)

ANE, e.g. ALKANES, saturated hydrocarbons i.e. no double or triple bonds.

They can be linear, branched, cyclo, substituted etc. (see later - haloalkanes etc.)

butane, pentylcyclohexane, cyclopropane

2,2-dimethylpropane, 2,2,3-trimethylbutane

Exemplar homologous series: CnH2n+2 for non-cyclo alkanes (n=1,2,3 etc.)

and CnH2n for cycloalkanes (n=3,4,5 etc.) isomeric with non-cyclo alkenes
 ALKENE HYDROCARBONS (unsaturated)

ENE, ALKENES, unsaturated hydrocarbons with a C=C double bond.

They can have more than one C=C, be linear, branched, cyclo

pent-1-ene, 3-ethylpent-1-ene, cyclobuta-1,3-

diene

or buta-1,3-diene, cyclohexene

Exemplar homologous series: CnH2n for non-cyclo alkenes (n=2,3 etc. with one C=C bond) isomeric
with cycloalkanes

and CnH2n-2 for cycloalkenes (n=3,4,5 etc., and with one C=C bond)

ALKYNE HYDROCARBONS (unsaturated)

YNE e.g. ALKYNES, unsaturated hydrocarbons with a C...C triple bond, examples:

ethyne, and propyne

Exemplar homologous series: CnH2n-2 for non-cyclo alkynes (with one triple bond)
 AROMATIC HYDROCARBONS (unsaturated)

'ARENES' are aromatic hydrocarbons with at least one benzene ring e.g.

or benzene, or methylbenzene

aliphatic/aromatic HALOGEN COMPOUNDS

Aliphatic: HALO e.g. HALOGENOALKANES (HALOALKANES)

C-X where X = F fluoro, Cl chloro.., Br bromo or I iodo

X is named as a prefix substituent in any type of organic molecule from alkanes to carboxylic acids.

chloromethane, bromoethane, dichlorodifluoromethane

1-bromo-1-chlorobutane, iodocyclohexane

1,2-dibromocyclopentane, chloromethylbenzene

or phenylchloromethane, which can also be classified as an aromatic compound

BUT the halogen is not attached directly to the benzene ring so it is not an aryl halide)
Exemplar homologous series: CnH2n+1X for non-cyclo halogenoalkanes (X=F,Cl,Br,I and n=1,2,3 etc.)

and CnH2n-1X for cyclohalogenoalkanes (n=3,4,5 etc. with one C-X bond)

A sub-CLASSIFICATION based on structural differences, which can have chemical

consequences on e.g. rate of reaction or products formed in a reaction.

o Halogenoalkanes are classified according to the atoms/groups attached to the

carbon of the halogen atom X.

o Primary halogenoalkanes have the structure R-CH2-X, R = H, alkyl, aryl etc. i.e.
apart from chloromethane they have one alkyl/aryl group attached to the C of the
C-X group.

e.g. chloroethane CH3CH2Cl

o Secondary halogenoalkanes have the structure R2CH-X, R = alkyl or aryl etc. i.e.
they have two alkyl/aryl groups attached to the C of the C-X group.

e.g. 2-bromobutane CH3CHBrCH2CH3

o Tertiary halogenoalkanes have the structure R3C-X, R = alkyl or aryl etc. i.e. they
have three alkyl/aryl groups attached to the C of the C-X group.

e.g. 2-iodo-2-methylpropane (CH3)3CI

Aromatic HALO ... ARENES (aromatic halogen compounds) have the halogen atom directly
attached to the benzene ring.

chlorobenzene, 1,4-dichlorobenzene, chloro-2-methylbenzene

 ALCOHOLS (aliphatic) and PHENOLS (aromatic)

Aliphatic OL e.g. ALIPHATIC ALCOHOLS. Aliphatic alcohols are classified as primary, secondary
and tertiary.

You can have diols, triols etc, with 2,3 etc, OH groups.

If there is a 'higher ranking' functional group in the molecule the substituent OH is called by the
prefix 'hydroxy' see * examples.

Primary aliphatic alcohols R-OH where R is alkyl

ethanol, ethan-1,2-diol

or 3-methylbutan-1-ol

4-hydroxybutanoic acid*

Secondary aliphatic alcohols R-CH(OH)-R' where R or R' are both alkyl (or aryl):

propan-2-ol, butan-2-ol, cyclohexanol, pentan-3-ol

cyclopentanol, 2-hydroxybutanoic acid*

Tertiary aliphatic alcohols RR'R"C-OH where R,R' or R" are all alkyl (or aryl):
 or 2-methylpropan-2-ol, 2-methylbutan-2-ol

or 3-methylpentan-1-ol

Exemplar homologous series: CnH2n+1OH for non-cyclic aliphatic alcohols (n=1,2,3 etc.)

or the less informative CnH2n+2O isomeric with aliphatic non-cyclo ethers

and CnH2n-1OH for cycloalcohols (n=3,4,5 etc. with one C-OH)

** linked to notes on oxidation of alcohols to aldehydes, ketones and carboxylic acids

AROMATIC PHENOLS ROH, R=aryl only, when the -OH is attached directly to a benzene ring the
molecule is called a phenol.

If there is a 'higher ranking' functional group in the molecule the substituent OH is called by the
prefix 'hydroxy' see * example.

or or phenol, 2-chlorophenol, 3-methylphenol

2,5-dichloro-4-methylphenol, 3-hydroxybenzoic acid*

 ETHERS

Alkyl/arylOXYalkane/arene e.g. ETHERS which have the C-O-C linkage.

The smaller carbon chain with the oxygen atom, is given the prefix in the name alkyl/aryl..oxyane

(alkyl-O- groups like CH3-O- are called alkoxy groups).

methoxymethane, methoxyethane, 2-ethoxypropane

ethoxyethane, 2-methoxypropane,

Exemplar homologous series: CxH2x+1-O-CyH2y+1 for non-cyclo ethers (x or y =1,2,3 etc.)

or the less informative CnH2n+2O (n=2,3,4 etc.) isomeric with non-cyclo aliphatic alcohols

or CnH2nO for cycloethers (n=2,3,4 etc. with one C-O-C linkage, non shown at the moment)

ALDEHYDES and KETONES (a group of carbonyl compounds)

AL e.g. ALDEHYDES have the -CHO group at the end of a carbon chain:

ethanal, propanal, or 2-methylpropanal

butanal, pentanal, 2-methylbutanal

Exemplar homologous series: CnH2n+1CHO for aliphatic aldehydes (n=0,1,2 etc.)

 or the less in formative CmH2mO (m=1,2,3 etc.) isomeric with ketones

ONE e.g. KETONES have the C-CO-C linkage within the carbon chain:

propanone, or butanone, pentan-2-one

or pentan-3-one

Exemplar homologous series: CxHxn+1-CO-CyH2y+1 for aliphatic ketones (x or y = 1,2,3, etc.)

or the less informative CnH2nO (n=3,4,5 etc.) isomeric with aldehydes

CARBOXYLIC ACIDS

OIC ACID e.g. CARBOXYLIC ACIDS with the -COOH group, substituents quoted as prefixes (
dioic if 2 -COOH groups):

aliphatic carboxylic acids

methanoic acid, propanoic acid, *aminoethanoic acid

2-methylpropanoic acid, *2-hydroxybutanoic acid

pentanoic acid, * ethanedioic acid

* examples of a dicarboxylic acids

If there is a 'higher ranking' functional group in the molecule the

substituent OH/NH2 is called by the prefix 'hydroxy/amino see * examples.

Exemplar homologous series: CnH2n+1COOH for aliphatic mono carboxylic acids (n=0,1,2,3 etc.)

or the less informative CnH2nO2 (n=1,2,3,4 etc.) isomeric with aliphatic esters

aromatic carboxylic acids (-COOH directly attached to the ring)

* 3-hydroxybenzoic acid, 2-ethanoylhydroxybenzoic acid

(Aspirin!)

2-chlorobenzoic acid, * benzene-1,2-dicarboxylic acid

(sometimes carboxylic rather than oic is used e.g. the dicarboxylic acids of benzene)

ACID ANHYDRIDES

OIC ANHYDRIDE e.g. CARBOXYLIC ACID ANHYDRIDES with the RCO-O-RCO linkage:

or ethanoic anhydride

or pentanoic anhydride

Exemplar homologous series: (CnH2n+1CO)2O for aliphatic mono carboxylic acids (n=2,3 etc.)
 ACID or ACYL CHLORIDES

OYL CHLORIDE e.g. CARBOXYLIC ACID or ACYL CHLORIDES with the -COCl group:

or propanoyl chloride, butanoyl chloride

or pentanoyl chloride, benzoyl

chloride

Exemplar homologous series: CnH2n+1COCl for aliphatic mono carboxylic acid chlorides (n=1,2,3
etc.)

ACID AMIDES

AMIDE e.g. CARBOXYLIC ACID AMIDES with the -CONH2 group:

or ethanamide, propanamide

butanamide, pentanamide, benzamide

Exemplar homologous series: CnH2n+1CONH2 for aliphatic mono carboxylic acid amides (n=0,1,2,3
etc.)
 ESTERS

alkyl/aryl OATE e.g. ESTERS of CARBOXYLIC ACIDS derived from ALCOHOLS or PHENOLS.

Esters have the -COOC- linkage:

methyl methanoate, propyl propanoate

ethyl propanoate, ethyl benzoate

Exemplar homologous series: CxH2x+1-COO-CyH2y+1 simple aliphatic esters (x=0,1,2, etc. and
y=1,2,3 etc.)

or the less informative CnH2nO2 (n=2,3,4 etc.) isomeric with carboxylic acids

ITRILES

The nitrile functional group consists of a carbon to nitrogen triple bond.

The name is based on the longest carbon chain, including the C of the nitrile group.

methanenitrile, , ,

ethanenitrile, , , , , ,

propanenitrile, , , , , ,
AMINES

PRIMARY AMINES have two hydrogen atoms and one alkyl or aryl group attached to the
nitrogen to form the amine or amino group -NH2.

ALIPHATIC: methylamine (aminomethane), , , ,

ethylamine (aminoethane), , , ,

SECONDARY AMINES have one hydrogen atom and two alkyl or aryl groups attached to the
nitrogen

ALIPHATIC: dimethylamine, , ,

ethylmethylamine, ,

diethylamine, ,

TERTIARY AMINES have no hydrogen atom and three alkyl or aryl groups attached to the
nitrogen

ALIPHATIC: trimethylamine, ,

ethyldimethylamine, ,

diethylmethylamine, ,
QUATERNARY AMMONIUM SALTS

If all for hydrogens of an ammonium ion are replaced with alkyl or aryl groups then an ionic
quaternary salt is formed.

e.g. the simplest is tetramethylammonium chloride, (CH3)4N+ Cl-

NITRO-AROMATIC COMPOUNDS

These have the nitro -NO2 group directly attached to the ring.

nitrobenzene, ; 1,3-dinitrobenzene,

2-methylnitrobenzene or 1-methyl-2-nitrobenzene,

DIAZONIUM SALTS and AZO DYES

Diazonium salts are formed when primary aromatic amines reaction with nitrous acid

The diazonium cation has a nitrogen - nitrogen triple bond system directly attached to the benzene
ring e.g.

(1) from phenylamine+

(2) from 4-methylphenylamine

In alkaline solution these diazonium salts couple with phenols and aromatic amines to form azo dyes
which have benzene rings linked with an azo -N=N- bond system e.g.

reacting (1) with phenol gives

reacting (2) with phenylamine gives

SULPHONIC ACIDS

These molecules have a strongly mono-basic acidic group -SO2OH directly attached to the
benzene ring e.g.

benzenesulphonic acid, ,(or benzenesulfonic acid)

2-, 3- or 4-methylbenzenesulphonic acid, , , (or ....sulfonic acid)