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JEE Main levelOne or more correct optionsDifficulty 2 of 3st192

Which of the following compounds have exactly three stereoisomers? (Count enantiomers and diastereomers as distinct.)

  1. A1,4-Dimethylcyclohexane
  2. B1-Bromo-2-chlorocyclopropane
  3. C1,3-Dichlorocyclopentane
  4. D1,2-Dimethylcyclohexane

Answer: C, D

Rings bearing two identical substituents at 1,2 or 1,3 positions give a meso cis form plus a trans pair, i.e. three stereoisomers; this applies to 1,2-dimethylcyclohexane and 1,3-dichlorocyclopentane. 1,4-Dimethylcyclohexane has only 2 (cis, trans). 1-Bromo-2-chlorocyclopropane has two stereocentres and no symmetry, so .
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