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JEE Advanced levelSingle correct optionDifficulty 3 of 3st104

A compound is drawn as a Fischer projection with vertical chain C1 (, top), C2, C3, C4 (, bottom): C2 has left H and right Br; C3 has left H and right Cl. This is subjected to these steps in order: (i) Br and H on C2 are interchanged; (ii) the whole projection is rotated by in the plane of the paper; (iii) Cl and H on C3 are interchanged. (C2 always denotes the carbon bearing Br.) What are the descriptors of the final compound and its relation to the starting compound? (Priorities: Br above C, Cl above C.)

  1. A(2R,3R); diastereomer of the starting compound
  2. B(2S,3R); identical to the starting compound
  3. C(2R,3S); enantiomer of the starting compound
  4. D(2S,3S); diastereomer of the starting compound

Answer: C

The starting compound is (2S,3R): C2 with Br on the right is S and C3 with Cl on the right is R. Step (i) inverts C2 to R, giving (2R,3R). Step (ii) is a rotation and changes nothing, although the numbering is read from the other end. Step (iii) inverts C3, giving (2R,3S). The final compound has every descriptor opposite to the start, so it is the enantiomer.
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