MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms III: Nucleophilic Substitution / Reactions of ethers and epoxides
JEE Main levelSingle correct optionDifficulty 2 of 3o3191

2,2-Dimethyloxirane (isobutylene oxide) is warmed with methanol containing a few drops of . The major product is

  1. A
  2. B (1-methoxy-2-methylpropan-2-ol)
  3. C
  4. D (2-methoxy-2-methylpropan-1-ol)

Answer: D

Acid protonates the epoxide oxygen and the bond to the tertiary carbon is weakened, so that carbon carries considerable positive charge. Methanol attacks this more substituted carbon. The oxygen of the original epoxide ends up as the primary alcohol, so the product is 2-methoxy-2-methylpropan-1-ol.
Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on Reactions of ethers and epoxides

More questions on Reactions of ethers and epoxides