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JEE Advanced levelSingle correct optionDifficulty 3 of 3st242

The compound shown is one stereoisomer of bicyclo[2.2.1]heptan-2-ol (norbornan-2-ol), drawn with wedges. Number the bridgehead next to the carbon as C1, the carbon as C2 and the other bridgehead as C4. Its configuration is

  1. A
  2. B
  3. C
  4. D

Answer: A

C2: priorities (attached to C,C,C) (attached to C,H,H) ; the drawn arrangement gives . C1: its three ring neighbours are C2 (O,C,H), C6 (C,H,H) and C7 (C,H,H); C2 is first, and C6 versus C7 is decided at the next sphere (C6 leads to C5 which bears C4, while C7 leads directly to C4, whose set (C,C,H) beats the (C,H,H) of C5), so the order is , giving . C4 with gives . The compound shown is ; option B is its enantiomer.
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