JEE Main Chemistry question

Coupling of diazonium salts with the following takes place in the order [of reactivity, lowest to highest]: phenoxide ion (I), phenol (II), aniline (III), anilinium ion (IV). [J & K CET 2004]

(A)IV < II < III < ICorrect
(B)IV > III < II < I
(C)II < IV < I < III
(D)I < II < IV < III

Answer: (A)

Solution

Azo coupling is an electrophilic aromatic substitution, so its rate increases with the electron density (nucleophilicity) of the coupling partner's ring. The anilinium ion (protonated amine, , an electron-withdrawing group) deactivates the ring the most and reacts slowest. Phenol () is a good but

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Question ID VK-150315