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JEE Main levelSingle correct optionDifficulty 2 of 3o1267

The enantiopure ketone shown (the stereocentre is fixed) is reduced with sodium borohydride, followed by work-up. What does the product mixture contain?

  1. AFour stereoisomers in equal amounts
  2. BA single stereoisomer only
  3. CA racemic mixture of two enantiomers
  4. DTwo diastereomers, each optically active, in unequal amounts

Answer: D

(R)-3-Methylpentan-2-one has one stereocentre. Reduction creates a second one at C-2, whose configuration may be either. Since the existing stereocentre is fixed, the two faces of the carbonyl are diastereotopic and attack is unequal. The product is a mixture of two diastereomers, each optically active, in unequal amounts.
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