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JEE Advanced levelSingle correct optionDifficulty 3 of 3st103

meso-Tartaric acid is drawn as a Fischer projection with at the top and bottom, and both OH groups on the right (C2 and C3). The Fischer projection corresponds to the eclipsed conformation about C2-C3. The rear carbon is then rotated by about the C2-C3 bond to give a staggered conformation. In that staggered conformation:

  1. Athe OH/OH dihedral angle is , the / dihedral angle is and the conformer has a centre of inversion
  2. Bthe OH/OH dihedral angle is but the / dihedral angle is , so the conformer is chiral
  3. Cthe OH/OH dihedral angle stays because rotation does not change the Fischer arrangement
  4. Dthe OH/OH dihedral angle is and the conformer has a mirror plane

Answer: A

A Fischer projection is an eclipsed conformation: the two OH groups (both right) eclipse each other at , and so do the two groups and the two H atoms. Rotating the rear carbon by takes every rear group exactly opposite its front partner, so OH/OH, / and H/H are all and the conformer is staggered. Pairs of identical groups opposite each other give an inversion centre at the bond midpoint, as expected for a meso compound.
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