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.