Aniline on treatment with NaNO _2 / HCl at about 0^ C gives a compound A, which on further treatment with CuCN / KCN gives a compound B, which when reacts with H _2 / Ni gives a compound C. The compound C on reaction with HNO _2 gives a compound D. The structure of D is:
A. C _6 H _5 -CH _2 -OH
Aniline ( C _6 H _5 NH _2) undergoes diazotization with NaNO _2 and HCl at 0^ C to form benzene diazonium chloride (A). C _6 H _5 NH _2 NaNO _2 / HCl , 0^ C C _6 H _5 N _2^+ Cl ^- (A) Benzene diazonium chloride reacts with CuCN / KCN to form benzonitrile (B) via the Sandmeyer reaction. C _6 H _5 N _2^+ Cl ^- CuCN / KCN C _6 H _5 CN (B) Benzonitrile is reduced by H _2 / Ni to form benzylamine (C). C _6 H _5 CN H _2 / Ni C _6 H _5 CH _2 NH _2 (C) Benzylamine, being an aliphatic primary amine, reacts with nitrous acid ( HNO _2) to form benzyl alcohol (D) with the evolution of nitrogen gas. C _6 H _5 CH _2 NH _2 HNO _2 C _6 H _5 CH _2 OH (D) Therefore, the structure of D is C _6 H _5 -CH _2 -OH . Answer: C _6 H _5 -CH _2 -OH
Related: Chemistry — Amines · All PYQ Banks