JEE Main · 2026 · 06 Apr 2026 · Shift 2 · Compounds Containing Nitrogen

The Hofmann bromamide reaction with $\mathrm{B}{\mathrm{r}}_2/KOH$ needs an unsubstituted amide $-\mathrm{CON}{\mathrm{H}}_2$, so the two N-substituted amides (the N-ethyl and the N-methyl amide) do not react at all. Of the unsubstituted amides, benzamide gives aniline, an aromatic amine that the Gabriel phthalimide synthesis cannot make because aryl halides do not undergo the required substitution. Phenylacetamide gives benzylamine, acetamide gives methylamine and cyclohexanecarboxamide gives cyclohexylamine, each a primary amine that the Gabriel route also delivers. Three compounds meet both requirements.