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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3091

-2-Methyloxirane is treated with sodium methoxide in methanol and then neutralised. Select the correct statements. (Priorities at the stereocentre of the epoxide: ring O ring H.)

  1. AThe product is -2-methoxypropan-1-ol, formed by inversion at the stereocentre.
  2. BThe product is 1-methoxypropan-2-ol.
  3. CThe stereocentre is not attacked, so the product is -1-methoxypropan-2-ol.
  4. DMethoxide attacks the less substituted ring carbon ().

Answer: B, C, D

Under basic conditions, ring opening is SN2 at the less hindered carbon, here . The stereocentre keeps all four of its bonds, so its geometry is retained. Its priorities become , the same order as before, so the descriptor remains . The last option corresponds to attack at the more hindered carbon, which is characteristic of acidic conditions.
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