Hofmann degradation
Quick Summary
The Hofmann degradation, also known as the Hofmann rearrangement, is a chemical reaction that converts an acid amide (RCONH₂) into an amine (RNH₂) with one fewer carbon atom. This transformation is achieved by treating the amide with sodium hypobromite.1
This reaction is named after the German chemist August Wilhelm von Hofmann, who conducted significant research in organic chemistry, including work on aniline and coal tar derivatives. His contributions laid groundwork for the aniline-dye industry. Hofmann also discovered formaldehyde and developed methods for determining molecular weights.2
Ask Britannica AI about this topic
Britannica doesn't have a full article on this topic, so we've curated a list of our relevant coverage.
amineOccurrence and sources of amines…among rearrangement reactions is the Hofmann reaction, in which an amide is treated with chlorine or bromine and an aqueous alkali (base).
Read More…among rearrangement reactions is the Hofmann reaction, in which an amide is treated with chlorine or bromine and an aqueous alkali (base).
Read More- amineElimination
…quaternary ammonium compounds is the Hofmann degradation, which takes place when the hydroxides are strongly heated, generating a tertiary amine; the least-substituted alkyl group is lost as an alkene.
Read More…quaternary ammonium compounds is the Hofmann degradation, which takes place when the hydroxides are strongly heated, generating a tertiary amine; the least-substituted alkyl group is lost as an alkene.
Read More