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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3st289

The compound shown is one stereoisomer of 2,4-dibromopentane. Which statements are correct?

  1. AIt has a plane of symmetry passing through C3
  2. BC3 is a pseudoasymmetric centre
  3. CIts configuration can be written as (2R,4S)
  4. DIt is a diastereomer of (2R,4R)-2,4-dibromopentane

Answer: A, C, D

The two stereocentres C2 and C4 carry the same groups and have opposite descriptors, and , so the compound is the meso form, (2R,4S)-2,4-dibromopentane, with a mirror plane through C3 perpendicular to the chain. C3 carries two hydrogens, so it cannot be a stereocentre of any kind and is not pseudoasymmetric (contrast 2,3,4-trichloropentane, where C3 carries H and Cl). The chiral (2R,4R) isomer differs from the meso form at only one centre, so the two are diastereomers.
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