7.6.7 Reactions of Amides

• Amides are formed from the condensation reaction of carboxylic acids or acyl chlorides with ammonia or amines
• The amide group (CONR₂) in these compounds can undergo reactions including
  • Hydrolysis with aqueous alkali or aqueous acid
  • Reduction with LiAlH₄

Hydrolysis of amides

• The -CON- group in substituted amides links two hydrocarbon sections of their molecules together
• This amide link can be broken down by hydrolysis by refluxing it with an acid or alkali
• The products of a non-substituted amide are:
  • Carboxylic acid
  • Ammonia

• The products of a substituted amide are:
  • Carboxylic acid
  • Primary amine

Hydrolysis of substituted and non-substituted amides

• Ammonia will react in excess acid to form an ammonium salt
• Carboxylic acid will get deprotonated in excess base to form a carboxylate ion

Amides are hydrolysed to carboxylic acids and ammonia or primary amine when refluxed with acid or alkali

Reduction of amides

• The C=O group in amides can be reduced by the strong reducing agent LiAlH₄ to form an amine
• The products of a non-substituted amide are:
  • A primary amine and water

• The products of a substituted amide are:
  • A secondary amine and water

Amides can be reduced to amines using LiAlH₄