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JEE Advanced 2019 Paper 2 · Chemistry · General Organic Chemistry and Isomerism · medium

A single pure stereoisomer is called a meso compound if it has stereocentres but is optically inactive because of an internal plane of symmetry.…

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A single pure stereoisomer is called a meso compound if it has stereocentres but is optically inactive because of an internal plane of symmetry. Which of the following exist(s) as a meso compound?
  1. A. cis-1,2-Dimethylcyclopentane
  2. B. trans-1,2-Dimethylcyclopentane
  3. C. trans-1,3-Dimethylcyclohexane
  4. D. trans-1,4-Dimethylcyclohexane
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Answer: A

For each compound the question is whether a single stereoisomer is superimposable on its mirror image while still containing stereocentres. In cis-1,2-dimethylcyclopentane the two methyls lie on the same face and a mirror plane perpendicular to the ring through the midpoint of C1–C2 maps the molecule onto itself, so it is meso; (A) is correct. The trans-1,2 isomer has C2C_2 symmetry only, so it is chiral and exists as an enantiomeric pair; (B) is wrong. In 1,3-dimethylcyclohexane it is the cis isomer that is meso, while the trans isomer is chiral; (C) is wrong. In 1,4-dimethylcyclohexane C1 and C4 carry two identical ring paths and are not stereocentres at all; the trans isomer is achiral but not meso; (D) is wrong. Only (A) is correct.
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