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JEE Main levelSingle correct optionDifficulty 2 of 3co250

The compound shown is treated with in methanol at 0 C. Which structure is the product?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: D

The drawn compound is ethyl 3-oxobutanoate (ethyl acetoacetate). NaBH4 reduces ketones but not esters, giving ethyl 3-hydroxybutanoate. LiAlH4 would reduce both groups (Structure A). Structure B would need full deoxygenation of the ketone and C would need ester-selective reduction.
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