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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3st147

Trihydroxyglutaric acid is (2,3,4-trihydroxypentanedioic acid). Counting configurational stereoisomers, select the correct statements.

  1. AThere are 4 stereoisomers in total
  2. BExactly two of the stereoisomers are meso (optically inactive)
  3. CExactly two of the stereoisomers are optically active and they are enantiomers of each other
  4. DC3 is a stereogenic centre in all four stereoisomers

Answer: A, B, C

Fischer-projection enumeration of the three OH groups (left/right) gives 8 arrangements; rotating by 180 degrees in the plane pairs them into 4 stereoisomers. Two of these have C2 and C4 with mirror-related configurations (2R,4S), giving two meso forms in which C3 is pseudoasymmetric. The other two have C2 and C4 of the same descriptor (2R,4R / 2S,4S) and form one enantiomeric pair; in them C3 carries two identical groups and is not stereogenic. So D is false.
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