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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3st073

Which of the following are meso compounds?

  1. A(2R,3S)-2,3-dibromobutane-1,4-diol
  2. B(2R,3S)-2,3-dichloropentane
  3. C(2R,4S)-2,4-dichloropentane
  4. D(1R,3R)-1,3-dimethylcyclohexane

Answer: A, C

A meso compound has stereocentres related by an internal mirror plane, which needs a symmetric constitution and opposite descriptors. The butane-1,4-diol and the pentane-2,4-diyl compound are symmetric and (R,S), so both are meso. 2,3-Dichloropentane is unsymmetrical (methyl versus ethyl ends) and therefore chiral. (1R,3R)-1,3-dimethylcyclohexane is the trans isomer, which is chiral; the cis isomer is (1R,3S).
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