Which of the following compound will not undergo an azo coupling reaction with benzene diazonium chloride.
(i) Aniline
(ii) Phenol
(iii) Anisole
(iv) Nitrobenzene
Option (iv) is the correct answer.
Explanation: Diazonium Chloride is a very weak electrophile; therefore, it reacts with any electron rich compound which contains electron donating groups; . The compounds should not contain electron withdrawing groups like: , etc.