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GATE 2024 CY – Question 42

Organic Chemistry · Reduction: Catalytic homogeneous and heterogeneous hydrogenation. Metal based reductions using Li/Na in liquid ammonia, magnesium, zinc, titanium, and samarium. Hydride transfer reagents: NaBH4, L-selectride, K-selectride, Luche reduction, LiAlH4 and DIBAL-H. · 2 marks · Multiple choice

The major products X and Y in the following reaction sequence are

Birch reduction and allylation followed by acidic hydrolysis and heating, with candidate X and Y structures.
  1. Option A in the figure
  2. Option B in the figure
  3. Option C in the figure
  4. Option D in the figure

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Show answer and explanation

Correct answer: (A) Option A in the figure

Explanation

The official pair of products X and Y is A. Track the carbon bearing the electron-withdrawing group through Birch reductive alkylation, then hydrolyze the enol ether and amide under the stated acidic conditions. The previous assignment to C used an incorrect final product connectivity.

Official GATE 2024 answer key: https://gate2026.iitg.ac.in/doc/download/2024/CYFinalAnswerKey.pdf