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

• In azo coupling reaction, the diazonium chloride plays the role of electrophillic substance which needs to be coupled with an activated aromatic compound (such as phenol, aniline or even anisole).

• But in case of Nitro benzene, nitro groups are electron-withdrawing groups, therefore they deactivate the benzene ring by forming canonical/resonating structures , after that the benzene ring cannot undergo azo coupling reaction.

Because of this situation nitrobenzene cannot perform this reaction whereas (i) Aniline ,

(ii) Phenol and (iii) Anisole can participate.

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