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JEE Advanced levelSingle correct optionDifficulty 3 of 3st040

How many stereoisomers does 1,2,3-trimethylcyclohexane have? Count enantiomers separately; the ring may be treated as planar for counting.

  1. A6
  2. B3
  3. C8
  4. D4

Answer: D

There are three stereocentres, so up to configurations, but C1 and C3 are equivalent by the symmetry of the molecule. Using up/down labels for the methyls on C1, C2, C3: is meso (achiral); is also achiral (mirror plane through C2); (same as ) and (same as ) are mirror images of each other and chiral. That is stereoisomers.
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