JEE Main Chemistry question

Which of the following compounds is not obtained when phthalic anhydride is treated with N₃H?

(A)Ring–CONH₂, ring–OH (unrelated amide/phenol pairing)
(B)Ring–COOH, ring–NH₂Correct
(C)A cyclic benzimidazolone-type structure
(D)A fused cyclic imide-type structure (phthalazinedione-type)

Answer: (B)

Solution

Phthalic anhydride reacting with hydrazoic acid (N₃H, a Schmidt-type reaction on the anhydride) converts one of the two carbonyls via the Schmidt pathway (loss of N₂, insertion of N into the chain), giving a cyclic product with one carbonyl converted to an amide/cyclic-imide-type nitrogen-containing ring, while

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Question ID VK-149487