MolSynapsequestion bank
MolSynapse / Question bank / Alcohols, Phenols and Ethers / Ethers: Williamson synthesis and cleavage
JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ap145

2,2-Dimethyloxirane is subjected to the following conditions. Select all correct product assignments.

  1. A/, then gives 1-methoxy-2-methylpropan-2-ol
  2. B, then gives 2-methylpropan-2-ol
  3. C (excess), then gives 2,2-dimethylpropan-1-ol
  4. D with a catalytic amount of gives 2-methoxy-2-methylpropan-1-ol

Answer: A, B, D

Strong nucleophiles (methoxide, hydride, Grignard) attack the less hindered carbon, whereas under acid catalysis the weak nucleophile methanol attacks the more substituted tertiary carbon, which bears more positive charge. Hydride gives , while would give 2-methylbutan-2-ol, not 2,2-dimethylpropan-1-ol.
Practice Alcohols, Phenols and Ethers More on Ethers: Williamson synthesis and cleavage

More questions on Ethers: Williamson synthesis and cleavage