The major product obtained in the following reactions is:
(A)(see structure)
(B)(see structure)
(C)(see structure)✓ Correct
(D)(see structure)
Answer: (C)
Solution
Follow the sequence step by step. The primary amine first undergoes the carbylamine reaction with CHClX3 and KOH to give an isocyanide. That isocyanide is then reduced under Pd/C with HX2 to the corresponding secondary amine, and finally KMnOX4 oxidises the benzylic secondary alcohol to a ketone. Collecting these changes, the major product carries the N-substituted amino group and a benzylic ketone at the oxidised position.
JEE Main · 2019 · 08 Apr 2019 · Shift 2 · Single correct option