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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3st197

For 1,2,3-trimethylcyclopropane (configuration only), which statements are correct?

  1. AIt has exactly two stereoisomers
  2. BThe rule with n = 3 correctly gives eight stereoisomers
  3. CNeither stereoisomer is optically active
  4. DThe stereoisomer in which one methyl is trans to the other two is chiral

Answer: A, C

On a planar three-membered ring the methyls can be all on one face (all-cis) or one methyl on the opposite face to the other two. By the ring symmetry all arrangements reduce to these two. Both have a mirror plane through one ring carbon and the midpoint of the opposite bond, so both are achiral. Hence 2 stereoisomers, none chiral, and the prediction fails.
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