1. HCN and CN – in synthesis Increasing carbon chain length

2. Reaction of haloalkanes with CN – RBr + CN –  RCN + Br – Reaction of carbonyl compounds with HCN: Aldehydes: RCHO + HCN  RCH(CN)COH Ketones: RCOR’ + HCN  RCR’(CN)COH Formation of C–C  N

3. Haloalkane  nitrile Reagents and conditions CN – ions, e.g. KCN(aq) in ethanol solvent Mechanism: Nucleophilic substitution charge lone pair C–C bond forms

4. Carbonyl  nitrile Reagents and conditions CN – ions in dilute acid, e.g. KCN(aq)/H 2 SO 4 (aq) Mechanism: Nucleophilic addition charge lone pair C–C bond forms

5. Nitriles in synthesis Reduction  amines H 2 and Ni catalyst Acid hydrolysis  carboxylic acids Aqueous acid, H + /H 2 O, e.g. HCl(aq) amine nitrile carboxylic acid nitrile