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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
Nitrobenzene
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D
None of the above
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Solution

The correct option is C Nitrobenzene
Diazonium salt 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 to form coupling product. It is called coupling reaction.
Coupling reaction takes place between benzene diazonium salt and phenol to p-Hydroxyazobenzene (an orange dye)

Coupling reaction takes place between benzene diazonium salt and aniline to p-aminobenzene (a yellow dye).Hence, option (c) is correct.

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