JEE Main · 2026 · 05 Apr 2026 · Shift 1 · Compounds Containing Nitrogen

In benzylamine the nitrogen lone pair sits on an $s{p}^3$ carbon, insulated from the ring by the $\mathrm{C}{\mathrm{H}}_2$ group and fully available, whereas in aniline it is delocalised into the ring; benzylamine is the stronger base, so statement A is correct. The Gabriel phthalimide synthesis works by ${\mathrm{S}}_{\mathrm{N}}2$ displacement and so yields only primary aliphatic amines; an aromatic amine such as 4-methoxyaniline, whose nitrogen lies on the ring, cannot be made this way, so statement B is incorrect. Hofmann bromamide degradation of phenylacetamide, ${\mathrm{C}}_6{\mathrm{H}}_5\mathrm{C}{\mathrm{H}}_2\mathrm{CON}{\mathrm{H}}_2$, removes one carbon to give benzylamine, a primary aliphatic amine rather than a primary aromatic amine, so statement C is incorrect. Diazotisation of 4-nitroaniline followed by warming hydrolyses the diazonium salt to 4-nitrophenol, a sound transformation, so that statement is correct. The incorrect statements are B and C.