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JEE Advanced levelSingle correct optionDifficulty 3 of 3st101

A staggered Newman projection of 2-bromo-3-chlorobutane is viewed along C2-C3. The front carbon (C2) has at 12 o'clock, Br at 4 o'clock and H at 8 o'clock. The rear carbon (C3) has Cl at 6 o'clock, H at 2 o'clock and at 10 o'clock. Which is the correct name of the stereoisomer? (CIP priorities: Br above C, Cl above C.)

  1. A(2S,3R)-2-bromo-3-chlorobutane
  2. B(2R,3S)-2-bromo-3-chlorobutane
  3. C(2R,3R)-2-bromo-3-chlorobutane
  4. D(2S,3S)-2-bromo-3-chlorobutane

Answer: D

At C2 the priorities are Br, then C3, then , then H. Exchange H with the rear carbon C3: H is then pointing away, C3 sits at 8 o'clock, and Br (4), C3 (8), (12) runs clockwise, i.e. R for the exchanged structure, so the real C2 is S. At C3 the priorities are Cl, then C2, then , then H. Exchange H (2 o'clock) with the front carbon C2: C2 now sits at 2 o'clock and H points toward the viewer. Cl (6), C2 (2), (10) runs anticlockwise; because H points toward the viewer the true sense is clockwise, so the exchanged structure is R and the real C3 is S. The result is (2S,3S).
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