When cyclohexanecarboxamide ${\mathrm{C}}_6{\mathrm{H}}_{11}\mathrm{CON}{\mathrm{H}}_2$ is treated with sodium hypochlorite (NaOCl) and sodium hydroxide (NaOH), which of the following products is formed?

Step-by-step solution

1. Recognise that the reaction conditions (NaOCl/NaOH) correspond to the Hofmann rearrangement, which removes a carbonyl carbon from an amide.
2. In the Hofmann rearrangement, the amide nitrogen becomes attached to the carbon chain after loss of CO${}_2$, giving a primary amine with one less carbon atom.
3. Cyclohexanecarboxamide has a six‑membered ring plus a carbonyl carbon; removal of the carbonyl carbon yields a six‑membered ring bearing a $-N{H}_2$ group, i.e., cyclohexylamine.
4. Eliminate the other options: cyclohexanone retains the carbonyl; cyclohexanol would require reduction; and aniline contains an aromatic ring, which is absent here.

Concept tested: Hofmann rearrangement of aliphatic amides

Published 13 September 2026 · How this solution was prepared and checked