Q. An azo compound is cleaved at the azo linkage by stannous chloride, to form two amines, 3-bromo- 4-amino toluene and 2-methyl-4-aminophenol. Which of the following is the suitable combination of A and B?

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Solution:

For the coupling reaction, diazonium ion should contain some electron withdrawing groups and the other compound should have electron releasing groups, i.e. should behave like a good nucleophile. Thus,
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Formation of 3-bromo-4-amino toluene and 2-methyl-4- amino phenol also support these structures for A and B.