Aniline is subjected to the following sequence of reactions: 1. ( CH ₃ CO )₂ O / Pyridine 2. Br ₂ / CH ₃ COOH 3. dil. HCl , heat 4. NaNO ₂ / HCl at 0 - 5^ C 5. CuBr / HBr The major final product formed is:

Step-by-step solution

The reaction sequence proceeds as follows: Step 1: Aniline reacts with acetic anhydride in the presence of pyridine to form acetanilide. This protects the amino group and moderates its activating effect. Step 2: 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 3: Acidic hydrolysis with dilute HCl and heat removes the acetyl protecting group, yielding p -bromoaniline. Step 4: Treatment of p -bromoaniline with NaNO