Chemical Properties of Cyanide and Isocyanide Preparation and Properties
→ Hydrolysis : On partial hydrolysis in basic and acidic medium, alkyl cyanides form amides. On complete hydrolysis amides give carboxylic acid in acidic medium and carboxylic acid salt in basic medium.
→ Alkyl isocyanide on complete hydrolysis in acidic medium form primary amine and formic acid.
→ Reduction : Alkyl halide on reduction in the presence of LiAlH4 or sodium and ethyl alcohol forms primary amine, this is called Mendius reduction.
→ In opposite of it alkyl isocyanide on hydrogenation in presence of Pt or Ni forms secondary amines.
→ Thorpe Reaction : In the presence of sodium catalyst in dry ether medium, two molecules of alkyl cyanide condenses to form dimer which is a member of imino cyanide family.
→ From Grigriard’s Reagents : Grignard reagents added to nitrile giving intermediate imine salts which upon hydrolysis give ketones.
→ Addition Reactions Alkyl isocyanide form addition compound with halogen, sulphur, ozone, mercuric oxide etc.
→ Isomerisaton Alkyl isocyanide when heated strongly for a long time is converted to more stable cyanide.