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JEE Advanced levelSingle correct optionDifficulty 3 of 3st288

Which one of the structures shown is NOT superimposable on its mirror image? Consider configuration only (treat rings as planar).

  1. AStructure (A)
  2. BStructure (B)
  3. CStructure (C)
  4. DStructure (D)

Answer: A

(A) is trans-1,2-dimethylcyclohexane: the two stereocentres have the same descriptor, (1R,2R) or (1S,2S), there is no mirror plane, and the compound is chiral. (B) cis-1,4-dimethylcyclohexane has a mirror plane through C1 and C4 and no stereocentres. (C) trans-1,3-dimethylcyclobutane has a mirror plane through C1 and C3. (D) is (2R,4S)-2,4-dibromopentane, the meso form, with a mirror plane through C3. Only (A) is chiral.
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