Question

The product X is :

• A.

  

• B.

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• C.

  

• D.

  

Hint:

Always protect \(-NH_2\) before halogenation → prevents polysubstitution.

Answer 1

The Correct Option is B

Concept:
• Acetylation (protection of \(-NH_2\))
• Electrophilic substitution (bromination)
• Deprotection (hydrolysis)

Step 1: Acetylation. \[ \text{-NH}_2 \xrightarrow{(CH_3CO)_2O} \text{-NHCOCH}_3 \] Reduces strong activating effect of \(-NH_2\), prevents multiple substitutions.

Step 2: Bromination. \(Br_2/CH_3COOH\) → \(-NHCOCH_3\) is ortho/para directing. Para position is preferred due to less steric hindrance.

Step 3: Deprotection. \[ \text{-NHCOCH}_3 \xrightarrow{H^+/H_2O} \text{-NH}_2 \]

Step 4: Final product. Bromine at para position, \(-NH_2\) group restored → p-bromoaniline.