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NEET levelSingle correct optionDifficulty 1 of 3o3262

The epoxide shown is treated with sodium methoxide in methanol, and then the mixture is worked up. Which structure is the product?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: C

The compound is methyloxirane (propylene oxide). Under basic conditions the methoxide attacks in an fashion at the less hindered CH2 carbon, opening the ring to the alkoxide, which is protonated to give 1-methoxypropan-2-ol, COCC(C)O.
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