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Amides with no substituent on the nitrogen when treated with a solution of Br2 or Cl2 in KOH yield only primary amines having one carbon atom less than the amides.
The reaction mechanism involves base-promoted N-bromination yielding N-Bromo amide as an intermediate. The N-Bromo amide then reacts with the hydroxide ion to produce N-bromamide anion, which rearranges with the migration of R group and loss of Br- ion to produce isocyanate.
Base catalyzed hydrolysis of isocyanate formed in the reaction mixture produces carbamate ion, which undergoes spontaneous decarboxylation resulting in the formation of amine.
List of Name Reaction of Organic Chemistry consist of detail Reaction Mechanism of all name reactions of Organic Chemistry.