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JEE Advanced levelSingle correct optionDifficulty 3 of 3st183

A Newman projection looks down the C2-C3 bond of 3-chlorobutan-2-ol, C2 in front. Front carbon (C2): CH at 12 o'clock, OH at 4 o'clock, H at 8 o'clock. Back carbon (C3): H at 2 o'clock, Cl at 6 o'clock, CH at 10 o'clock. What is the configuration of the compound?

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

Answer: B

At C2 the priorities are OH > C3 (Cl,C,H) > CH > H. C3 points away from the viewer, and OH (4 o'clock) CH (12) H (8), i.e. priorities 1 3 4, run counter-clockwise; with priority 2 pointing away this corresponds to S (swapping priorities 2 and 4 would give a clockwise 1-2-3 sequence, R, so the real centre is S). At C3 the priorities are Cl > C2 (O,C,H) > CH > H, and C2 points towards the viewer; Cl (6) CH (10) H (2) runs clockwise, which with priority 2 towards the viewer is the same as counter-clockwise with it away, so C3 is also S. The compound is (2S,3S); rotation about C2-C3 does not change configuration.
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