A compound A (C₉H₁₁NO) reacts with Br₂/NaOH to give X. X reacts with NaNO₂/HCl to give Y. Y with CuCN followed by hydrolysis gives Z. Hydrolysis of A also gives Z. Identify compound A.

Question

Shiksha Nation · Accepted Answer

Solution:
Br₂/NaOH indicates Hofmann bromamide reaction.
A must be an amide.
After Hofmann degradation, amine forms. Diazotization and Sandmeyer reaction finally produce carboxylic acid.
Hydrolysis of original compound also gives same acid.
Therefore, compound A is p-methyl benzamide.
Correct Answer: Structure given in Option (3)

A compound A (C₉H₁₁NO) reacts with Br₂/NaOH to give X. X reacts with NaNO₂/HCl to give Y. Y with CuCN followed by hydrolysis gives Z. Hydrolysis of A also gives Z. Identify compound A.

Verified Answer