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Chapter 6: Problem 147

Coupling reaction takes place when benzene diazonium chloride is treated with (a) Benzaldehyde (b) \(\alpha\) -naphthol (c) N,N-dimethylaniline (d) anisole

Short Answer

Expert verified
a) Benzaldehyde b) α-naphthol c) N,N-dimethylaniline d) Anisole Answer: (b) α-naphthol

Step by step solution

01

Identify Coupling Reaction

In a coupling reaction, benzene diazonium chloride reacts with an active aromatic compound to form an azo compound. The general reaction can be represented as: Aromatic compound + Benzene diazonium chloride -> Azo compound Now, let's analyze the given options.
02

Analyze Option (a) - Benzaldehyde

Benzaldehyde is an aromatic aldehyde which does not possess an active site for the coupling reaction to occur. Therefore, benzaldehyde does not undergo a coupling reaction with benzene diazonium chloride.
03

Analyze Option (b) - \(\alpha\) -naphthol

\(\alpha\)-naphthol is an aromatic phenol, which contains an active hydroxyl group (-OH) attached to the aromatic ring. Phenols are highly reactive aromatic compounds that can undergo coupling reactions with diazonium salts, such as benzene diazonium chloride. Therefore, when \(\alpha\)-naphthol is treated with benzene diazonium chloride, a coupling reaction occurs, resulting in the formation of an azo compound. The reaction can be represented as: \(\alpha\)-naphthol + Benzene diazonium chloride -> Azo compound
04

Analyze Option (c) - N,N-dimethylaniline

N,N-dimethylaniline is an aromatic amine, but the presence of the dimethyl (N,N) group makes it less reactive toward coupling reactions with diazonium salts. The resonance electron donation from the aromatic ring to the nitrogen is hindered by the attached dimethyl groups, thus making it a poor candidate for a coupling reaction.
05

Analyze Option (d) - Anisole

Anisole is an aromatic ether, and ethers generally do not possess an active site for coupling reactions to occur. Therefore, anisole does not undergo a coupling reaction with benzene diazonium chloride.
06

Identify the Correct Option

Based on our analysis, we found that option (b) \(\alpha\)-naphthol is an aromatic phenol, which can undergo a coupling reaction with benzene diazonium chloride to form an azo compound. Therefore, the correct answer is (b) \(\alpha\)-naphthol.

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