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JEE Advanced levelSingle correct optionDifficulty 3 of 3o3152

(S)-2-Phenyloxirane (styrene oxide) is opened in two ways: (i) with methanol containing a catalytic amount of , where methanol attacks the carbon that best carries positive charge, with inversion there; (ii) with in methanol, where methoxide attacks the less hindered carbon. Which pair of major products is correct?

  1. A(i) (S)-2-methoxy-1-phenylethan-1-ol; (ii) (R)-2-methoxy-2-phenylethan-1-ol
  2. B(i) (R)-2-methoxy-2-phenylethan-1-ol; (ii) (S)-2-methoxy-1-phenylethan-1-ol
  3. C(i) (S)-2-methoxy-2-phenylethan-1-ol; (ii) (S)-2-methoxy-1-phenylethan-1-ol
  4. D(i) (R)-2-methoxy-2-phenylethan-1-ol; (ii) (R)-2-methoxy-1-phenylethan-1-ol

Answer: B

(i) Under acid the benzylic C-O bond is loosened, methanol attacks the benzylic carbon from the back, and forms with inverted geometry. Its priorities are (O,H,H) (C,C,C) , and the CIP calculation gives R. (ii) Methoxide attacks , so the stereocentre of keeps its geometry, with priorities , giving S. Both assignments were checked with a CIP calculation.
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More questions on SN1 vs SN2: substrate, nucleophile, solvent, leaving group