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Question 59

Aniline dissolved in dilute HCl is reacted with sodium nitrite at 0°C. This solution was added dropwise to a solution containing an equimolar mixture of aniline and phenol in dilute HCl. The structure of the major product is:

Aniline becomes a diazonium salt first, then the Ar-N2+ prefer -NH2 over -OH as it has a better +M effect. Hence A would be the right answer.

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