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NEET levelSingle correct optionDifficulty 1 of 3st304

The compound shown is 1,2-dimethylcyclohexane with the two methyl groups on opposite faces of the ring. Considering configuration only, it is

  1. Achiral, and exists as a pair of enantiomers
  2. Ba meso compound
  3. Cachiral, because it has no stereocentre
  4. Doptically inactive, because ring flipping converts it into its mirror image

Answer: A

The compound is trans-1,2-dimethylcyclohexane, here (1S,2S). Both ring carbons bearing methyl are stereocentres and they have the same descriptor, so there is no internal mirror plane (a plane bisecting the C1-C2 bond would require the methyls to be on the same face). The compound is chiral; its mirror image (1R,2R) is a distinct enantiomer. Ring flipping interconverts chair conformers of the same configuration and never produces the enantiomer.
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More questions on Cyclic stereoisomers (cyclopropane, cyclobutane, cyclohexane) from structures