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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3st301

The two structures shown (left and right) are stereoisomers of tartaric acid drawn with opposite wedge patterns at both carbons. Which statements are correct?

  1. AThe two structures represent the same compound
  2. BEach structure represents an optically inactive compound
  3. CThe two structures are enantiomers
  4. DBoth structures can be described as (2R,3S)-2,3-dihydroxybutanedioic acid

Answer: A, B, D

In the left structure the centres are and ; inverting both gives and in the right structure. Because the two ends of tartaric acid are identical, (2S,3R) renumbered from the other end is (2R,3S). Both drawings are therefore the meso acid, which has an internal mirror plane, is achiral and is optically inactive. A compound that is superimposable on its mirror image cannot have an enantiomer, so (C) is wrong; the right-hand drawing is simply the left one viewed from the other side.
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