Carbon- Carbon Bond Formation

Formation of Nitriles: Nitrile group is –CN.
 1) Haloalkanes to Nitriles: Haloalkanes reacted with sodium or potassium
cyanide NaCN/ KCN in ethanol. In this reaction length of carbon chain increased. This is an
example of nucleophilic substitution.
 2) Aldehydes/ Ketones to Nitriles: Aldehydes/ ketones react with hydrogen cyanide HCN. A
nucleophilic addition reaction. Increases number of carbon atoms. Product is hydroxynitrile.
Already seen mechanism for this.
 3) Reduction of Nitriles: Nitriles can be reduced to amines by reacting with
hydrogen in presence of nickel catalyst. 4 hydrogens added.
 4) Hydrolysis of Nitriles: Nitriles undergo hydrolysis to form carboxylic acid.
Heated with water and dilute aqueous acid e.g. HCl (aq).

Forming Carbon- Carbon Bonds to Benzene: Alkylation and acylation covered already form C-C
bonds to benzene.