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 \( (A) \).
Show Hint
The Hofmann bromamide reaction and diazotization are key steps in identifying and synthesizing amines.
To identify compound \( A \) with the molecular formula \( \text{C}_9\text{H}_{11}\text{NO} \), let's go through the reactions step-by-step:
Compound \( A \) reacts with \( \text{Br}_2/\text{NaOH} \) to give compound \( X \). This reaction is characteristic of primary amides or amines undergoing the Hofmann bromamide degradation, which converts them into amines with one carbon atom less.
The amine \( X \) is then reacted with \( \text{NaNO}_2 \) in dilute HCl to give compound \( Y \). This corresponds to the diazotization reaction where primary aromatic amines form diazonium salts.
When compound \( Y \) is treated with \( \text{CuCN} \), it leads to the formation of a cyano compound which, upon hydrolysis, gives compound \( Z \). Hydrolysis of a nitrile leads to an acid, implying that \( Z \) is a carboxylic acid.
Furthermore, it is given that compound \( A \) on hydrolysis directly gives compound \( Z \), suggesting that \( A \) might initially be an amide which upon hydrolysis directly forms the corresponding carboxylic acid.
Considering these reactions, a suitable candidate for \( A \) is an aromatic amide with the formula for benzamide derivatives. The correct option showing this structure is:
The correct structure of compound \( A \) is option 1.
