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JEE Main levelOne or more correct optionsDifficulty 2 of 3st273

The compound shown is 1,3-dimethylcyclohexane drawn without stereochemistry. Treat the ring as planar and consider configuration only. Which of the following statements are correct?

  1. AIt has 3 stereoisomers in total
  2. BThe cis isomer is a meso compound
  3. CThe trans isomer exists as a pair of enantiomers
  4. DIt has 4 stereoisomers because it has two stereocentres and no symmetry

Answer: A, B, C

C1 and C3 are stereocentres (the two ring paths from each are of different length). The molecule has a symmetry element exchanging C1 and C3: the plane through C2 and C5. In the cis isomer both methyls lie on the same face and this plane is a mirror plane, so cis is meso. In the trans isomer the methyls are on opposite faces, the plane is not a mirror plane, and trans is chiral: and . Total , not 4.
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