JEE Advanced levelSingle correct optionDifficulty 3 of 3nc141
Aniline is treated successively with (i) NaNOX2 / dil. HCl at 273-278 K to give A, (ii) CuCN/KCN to give B, and (iii) HX2 / Ni to give C. C is
ACX6HX5NHX2
BCX6HX5CHX2CHX2NHX2
CCX6HX5CHX2NHX2
DCX6HX5CONHX2
Answer: C
A is benzenediazonium chloride and B is benzonitrile, CX6HX5CN, formed by the Sandmeyer reaction. Catalytic hydrogenation reduces the nitrile group to −CHX2NHX2, giving benzylamine, a primary amine with one carbon more than aniline.