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

Options

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

Answer

D

Explanation

Nitrobenzene will not undergo azo coupling reaction with benzene diazonium chloride while other three undergo diazo coupling reaction very easily. Diazonium cation is a weak `E^(+)` and hence reacts with electron rich compounds containing electron donating group i.e., `-OH_(1) - NH_(2) and -OCH_(3)` groups and not with compounds containing electron withdrawing group, i.e., `NO_(2)` etc