JEE Main · 2019 · 09 Jan 2019 · Shift 1 · Compounds Containing Nitrogen

Chlorination of toluene under light drives free-radical substitution at the benzylic position, giving benzyl chloride $\mathrm{C}{}_6\mathrm{H}{}_5\mathrm{CH}{}_2\mathrm{Cl}$ as compound A. Treating that with $\mathrm{AgCN}$ gives the isocyanide rather than the nitrile, since silver cyanide is largely covalent and the nitrogen attacks the carbon, so compound B is benzyl isocyanide $\mathrm{C}{}_6\mathrm{H}{}_5\mathrm{CH}{}_2\mathrm{NC}$, which on reduction would give benzylamine. Hence A is benzyl chloride and B is benzyl isocyanide.