Starting molecule

Type of reaction

Products

Alkanes

Thermal cracking

alkanes + alkenes

Catalytic cracking

alkanes (branched) + cycloalkanes

Complete combustion

carbon dioxide + water

Methane

Free-radical substitution

haloalkane

Alkenes

Hydrogenation

Electrophilic addition

- HBr

- Br₂

- H₂SO₄

bromoalkane

dibromoalkane

alkyl hydrogensulphate

Hydrolysis

alcohol

Addition polymerisation

poly(alkene)

Haloalkanes

Nucleophilic substitution

- KCN

- NaOH(aq)

- NH₃

nitrile (then reduction to amine)

alcohol

amine (1^o, 2^o, 3^o, 4^o salt)

Elimination

alkene

Alcohols

Elimination

alkene

Oxidation (primary)

aldehyde

Oxidation (secondary)

ketone

Nucleophilic addition-elimination

ester

Esterification

ester

Aldehydes

Oxidation

carboxylic acids

Reduction - H₂/Ni

1^o alcohol

Nucleophilic addition

- H₂

- NaBH₄

- CN^-

1^o alcohol

1^o alcohol

hydroxylnitrile

Ketones

Reduction - H₂/Ni

2^o alcohol

Nucleophilic addition

- H₂

- NaBH₄

- CN^-

2^o alcohol

2^o alcohol

hydroxylnitrile

Carboxylic acids

Neutralisation

carboxylate salt + water + carbon dioxide

Esterification

ester

then saponification to alcohol + carboxylate salt

Ester

Hydrolysis

alcohol + carboxylic acid

Acyl chloride

Nucleophilic addition-elimination (acylation)

- H₂O

- ROH

- NH₃

- RNH₂

carboxylic acid + HCl

ester + HCl

amide + NH₄Cl

N-substituted amide + RNH₃Cl

Electrophilic substitution

aromatic ketone

Acid anhydride

Nucleophilic addition-elimination (acylation)

- H₂O

- ROH

- NH₃

- RNH₂

carboxylic acid

ester + carboxylic acid

amide + carboxylic acid

N-substituted amide + carboxylic acid

Benzene

Electrophilic substitution

nitrobenzene

then reduction to phenylamine

Hydrogenation

cyclohexane

Electrophilic substitution

aromatic ketone