Question

Which of the following compound will not undergo azo coupling reaction with benzene diazonium chloride.

• A. Nitrobenzene
• B. Anisole
• C. Phenol
• D. Aniline

Answer 1

The correct option is A Nitrobenzene

Azo coupling reaction

In azo coupling reaction benzene diazonium chloride acts as an electrophile. Benzene attached with an activating group (electron donating group) will react with weak electrophile benzene diazonium chloride to form azo compound. Generally, these compounds are known as Dyes.

A)
B)
C)
D)
In options $A,B$ and $C$ strong activating group (electron donating group) is attached to benzene ring so they will undergo diazo coupling reaction.
But, In Option $D$ (nitrobenzene), the nitro group is a strong deactivating group (electron withdrawing group). So, it will not undergo azo coupling reaction with benzene diazonium chloride.

Hence, the correct answer is option $\left(D\right)$.