JEE Main Chemistry question

By which of the following reagents can the conversion of methyl salicylate to 2-acetylphenyl-type product (ring–COOCH₃ to ring with an α-methyl ketone side chain) be effected?

(A)2 CH₃MgBr and H₃O⁺Correct
(B)HOCH₂–CH₂OH, H⁺, LiAlH₄, ether, 2CH₃MgBr, H₃O⁺
(C)HOCH₂–CH₂OH, H⁺, 2CH₃MgBr, H₃O⁺
(D)HOCH₂–CH₂OH, H⁺, H₂, Pt, CH₃OH, H⁺

Answer: (A)

Solution

Two equivalents of CH₃MgBr add successively to the ester carbonyl of methyl salicylate (first displacing methoxide to form the ketone intermediate in situ, then adding a second time to

See the full step-by-step solution

Create a free account to read the complete working, and practise questions like this in a timed test.

Create a free account

Question ID VK-149381