Question

Identify \(X\) and \(Y\) of the following reaction sequence

• A. 1
• B. 2
• C. 3
• D. 4

Hint:

Aniline is first protected as acetanilide before bromination to avoid polysubstitution. Primary aromatic amines give isocyanides with \(CHCl_3/KOH\) in the carbylamine reaction.

Answer 1

The Correct Option is D

Step 1: Sequence the transformations.
PhNO₂ → (H₂/Pd) → PhNH₂. PhNH₂ → (Ac₂O/pyridine) → PhNHCOCH₃ = acetanilide (X). Acetanilide → (Br₂/AcOH) → p-bromoacetanilide. Hydrolysis → p-bromoaniline. Carbylamine test (CHCl₃, alc. KOH, Δ) converts the primary amine to p-bromophenyl isocyanide (Y).

Step 2: Final Answer:
X = acetanilide, Y = p-bromophenyl isocyanide (option 4).