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JEE Advanced levelSingle correct optionDifficulty 3 of 3o3273

The single-enantiomer epoxide shown is reduced with in ether, followed by aqueous work-up. Which product is formed?

  1. A(R)-1-phenylethanol
  2. B2-Phenylethanol
  3. CRacemic 1-phenylethanol
  4. D(S)-1-phenylethanol

Answer: D

The compound is (R)-styrene oxide. Hydride attacks the less hindered CH2, so the stereogenic benzylic C-O bond is not broken and the arrangement is retained. Writing the product as O[C@@H](C)c1ccccc1 and checking CIP gives S: in the epoxide CH2(O,H,H) outranks phenyl, but in the product phenyl outranks CH3, so the letter changes although the arrangement is retained. Product: (S)-1-phenylethanol.
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