Aniline dissolved in dilute HCl is reacted with sodium nitrite at \(0^\circ\mathrm{C}\). This solution was added dropwise to a solution containing equimolar mixture of aniline and phenol in dil. HCl. The structure of the major product is
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The Correct Option is C
Solution and Explanation
Step 2: the diazonium salt is added to an equimolar mixture of aniline and phenol in dilute HCl (acidic medium).
In acidic medium phenol exists mostly un-ionised (not as the highly reactive phenoxide), so it couples poorly, while the amino group of aniline is only partly protonated and still strongly activating. Coupling with aromatic amines occurs best at pH about 4-5.
The electrophilic diazonium ion attacks the para position of aniline (para to \(\mathrm{-NH_2}\)) to give \(p\)-aminoazobenzene (4-aminoazobenzene), \(\mathrm{C_6H_5-N=N-C_6H_4-NH_2}\). Option (2) (diazoaminobenzene, N-coupling) forms only under neutral/less acidic conditions and rearranges to the para product in acid.
Answer: (3) \(p\)-aminoazobenzene
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