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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3st233

The compound shown is 2,3,4-trichloropentane drawn without stereochemistry. Counting configurational isomers only, which of the following statements are correct?

  1. AIt has a total of 4 stereoisomers
  2. BTwo of its stereoisomers are meso compounds
  3. CC3 is a stereocentre in every one of its stereoisomers
  4. DIn the chiral stereoisomers C3 carries two identical groups and is not a stereocentre

Answer: A, B, D

C2 and C4 are ordinary stereocentres. C3 carries , and two groups that differ only in configuration, so C3 is a pseudoasymmetric centre. When C2 and C4 have opposite descriptors the two groups on C3 are enantiomeric and C3 has two distinct arrangements ( and ); both of these molecules have a mirror plane through C3, giving 2 meso forms. When C2 and C4 have the same descriptor or the two groups on C3 are identical, so C3 is not a stereocentre and this gives one pair of enantiomers. Total stereoisomers.
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