A compound ‘A’ with molecular formula \( \text{C}_9\text{H}_{11}\text{NO} \) reacts with \( \text{Br}_2/\text{NaOH} \) to give \( (X) \). On reaction with \( \text{NaNO}_2 \) in dilute HCl, it gives compound \( (Y) \). When \( (Y) \) is treated with CuCN, followed by hydrolysis, it gives \( (Z) \). The compound \( (A) \) on hydrolysis also gives compound \( (Z) \). Identify compound \( (A) \).
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The Hofmann bromamide reaction and diazotization are key steps in identifying and synthesizing amines.
Step 1: Reaction with \( \text{Br}_2/\text{NaOH} \).
The given molecular formula suggests an amine group, which reacts with bromine and sodium hydroxide (the Hofmann bromamide reaction) to give a primary amine. The compound \( (A) \) contains a benzylic amine group, suggesting it undergoes this reaction.
Step 2: Reaction with \( \text{NaNO}_2 \) and dilute HCl.
The reaction of the amine group with nitrous acid gives diazonium salt, confirming the structure of \( A \).
Step 3: Treatment with CuCN and hydrolysis.
The treatment of diazonium salts with copper cyanide forms a substituted aromatic compound, and hydrolysis gives the corresponding phenyl group.
Step 4: Conclusion.
Thus, compound \( (A) \) is \( \text{C}_6\text{H}_5\text{C}\left(\text{NH}_2\right)\text{CH}_3 \).
Final Answer:
\[
\boxed{\text{C}_6\text{H}_5\text{C}\left(\text{NH}_2\right)\text{CH}_3}
\]
