Write the balanced overall chemical equation for the Hofmann rearrangement of benzamide (${\mathrm{C}}_6{\mathrm{H}}_5\mathrm{CON}{\mathrm{H}}_2$) using sodium hypochlorite ($\mathrm{NaOCl}$) and sodium hydroxide ($\mathrm{NaOH}$). Also name the organic product formed.

Step-by-step solution

1. The Hofmann rearrangement converts a primary amide into a primary amine with loss of one carbon atom.
2. Write the reactants: benzamide, NaOCl (source of ClO⁻) and two equivalents of NaOH.
3. Balance the nitrogen atoms: one nitrogen on each side, appearing in benzamide and aniline.
4. Balance the carbon atoms: the carbonyl carbon of the amide becomes the carbon of carbonate (CO₃²⁻).
5. Balance oxygen and hydrogen atoms, adding water as needed.
6. The final balanced equation is: ${\mathrm{C}}_6{\mathrm{H}}_5\mathrm{CON}{\mathrm{H}}_2+\mathrm{NaOCl}+2NaOH\to {\mathrm{C}}_6{\mathrm{H}}_5\mathrm{N}{\mathrm{H}}_2+\mathrm{NaCl}+\mathrm{N}{\mathrm{a}}_2\mathrm{C}{\mathrm{O}}_3+{\mathrm{H}}_2\mathrm{O}$.
7. The organic product formed is aniline (${\mathrm{C}}_6{\mathrm{H}}_5\mathrm{N}{\mathrm{H}}_2$).

Concept tested: Hofmann rearrangement of amides

Published 2 September 2026 · How this solution was prepared and checked

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