The product (P) formed from the following multistep reaction is :-
(A)(see structure)
(B)(see structure)
(C)(see structure)
(D)(see structure)✓ Correct
Answer: (D)
Solution
Bromination of 4-nitrotoluene places the bromine ortho to the methyl group and meta to the nitro group, since both groups direct to the same carbon. Catalytic hydrogenation then reduces the nitro group to an amino group. Treatment with nitrous acid at low temperature converts the amino group into a diazonium group, and hypophosphorous acid replaces the diazonium group by hydrogen, removing it from the ring. What remains is a toluene ring carrying bromine ortho to the methyl group, which is ortho-bromotoluene.
JEE Main · 2023 · 08 Apr 2023 · Shift 2 · Single correct option
