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Question

Which of the following compounds will not undergo azo coupling reaction with benzene diazonium chloride?

A
Aniline
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B
Phenol
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C
Anisole
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D
Nitrobenzene
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Solution

The correct option is D Nitrobenzene
Diazonium cation is a weak electrophile and hence it reacts with electron-rich compounds containing electron-donating groups such as OH, NH2 and OCH3 groups and not with compounds containing electron-withdrawing groups such as NO2, etc.

Hence, option D is correct.

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