Question

What is the product of the following reaction?

(a) 2-Amino-4-phenylazophenol

(b) 6-Amino-2-phenylazophenol

(c) 2-Amino-5-phenylazophenol

(d) 2-Amino-3-phenylazophenol

The question was asked in an interview for internship.

My question is taken from Diazonium Salts Chemical Reactions in division Amines of Chemistry – Class 12

Answer 1

Correct answer is (c) 2-Amino-5-phenylazophenol

Explanation: The reactant (o-aminophenol) consists of both hydroxy and amino groups. Since the reaction takes place in an acidic medium, the coupling occurs at para position (first preferred) with respect to the amino group. If the reaction was to take place in a basic medium, the coupling would have occurred at para position with respect to hydroxy group.