Illustrated Glossary of Organic Chemistry

Hofmann degradation (Hofmann rearrangement): Reaction of a primary amide with molecular bromine and aqueous strong base produces a primary amine, with one fewer carbon than the starting amide. This carbon is lost as a molecule of carbon dioxide.

In this Hofmann rearrangement, benzamide (a primary amide) is reacted with Br2 and aqueous NaOH to produce aniline (a primary amine) and CO2. Groups are colored to show origin of the carbon atoms in the reaction products.