JEE MainChemistryAmines
Aniline undergoes the following sequence of reactions to form a major product P: (i) Ac ₂ O , pyridine (ii) Br ₂ , CH ₃ COOH (iii) H ₃ O ^+ (iv) NaNO ₂ , HCl , 273-278 K (v) CuCN , KCN The final major product P is:
Options
- Ap -Bromobenzonitrile
- B2,4,6-Tribromobenzonitrile
- Cp -Cyanoaniline
- Dm -Bromobenzonitrile
Correct answer
A. p -Bromobenzonitrile
Step-by-step solution
Step (i): Aniline reacts with acetic anhydride ( Ac ₂ O ) in the presence of pyridine to form acetanilide. This protects the amino group and reduces its activating effect. Step (ii): Bromination of acetanilide with Br ₂ in acetic acid yields p -bromoacetanilide as the major product due to steric hindrance at the ortho position. Step (iii): Acidic hydrolysis ( H ₃ O ^+ ) of p -bromoacetanilide removes the acetyl group, yielding p -bromoaniline. Step (iv): Diazotization of p -bromoaniline with NaNO ₂ and HCl at 273-2