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JEE Advanced levelSingle correct optionDifficulty 3 of 3st079

How many stereoisomers does cyclohexane-1,2,3-triol have? Treat the ring as planar and count cis/trans isomers, with each distinct compound or enantiomer counted once.

  1. A4
  2. B3
  3. C6
  4. D8

Answer: A

Three ring carbons carry OH, giving 8 up/down combinations. All-cis is meso, and the isomer with C2 trans to both C1 and C3 (C1 and C3 cis) is also meso, with C2 acting as a pseudoasymmetric centre. The isomers with C1 or C3 alone trans to the others form one enantiomeric pair, and orbit counting under the in-plane flip gives 4 in total.
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