Question

The product of the following reaction sequence is

$NH_2$

(i) Acetic anhydride/pyridine (ii) $Br_2$ in $CH_3COOH$ (iii) $H_3O^+$, heat $\longrightarrow$ Product (Major)

• A. Br $NH_2$
• B. Br $NH_2$
• C. Br $NH_2$
• D. Br Br
• E. Br

Answer 1

Answer: (B)

p–Bromoaniline (Option (2))

Answer 2

1. Step (i) – Acetylation:
   Aniline (benzene–NH₂) is converted to acetanilide (benzene–NHCOCH₃) using acetic anhydride in pyridine. This protects the amino group.

2. Step (ii) – Bromination:
   Acetanilide undergoes electrophilic aromatic substitution with Br₂ in CH₃COOH. The acetyl group directs bromination mainly to the para position, forming p–bromoacetanilide.

3. Step (iii) – Hydrolysis:
   Acidic hydrolysis (H₃O⁺, heat) removes the acetyl group, regenerating the amino group. The final product is p–bromoaniline.