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JEE Main levelSingle correct optionDifficulty 2 of 3o1269

The ketone shown is reduced with sodium borohydride to a mixture of alcohols (both cis and trans isomers). Counting configurational stereoisomers of the alcohol constitution, how many stereoisomers does the product have?

  1. A1
  2. B2
  3. C4
  4. D3

Answer: B

4-Methylcyclohexanone gives 4-methylcyclohexan-1-ol. The two ring carbons C-1 and C-4 are stereogenic only as a pair, giving cis and trans isomers, and the ring has a plane of symmetry so each is achiral. RDKit enumeration gives 2 stereoisomers.
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