MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms III: Nucleophilic Substitution / Epoxide and ether cleavage regiochemistry on drawn structures
JEE Main levelSingle correct optionDifficulty 2 of 3o3265

The epoxide shown is treated with methylmagnesium bromide in ether, followed by aqueous acid work-up. Which structure is the product?

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

Answer: D

The compound is 2,2-dimethyloxirane. A Grignard reagent is a strong, hindered-sensitive nucleophile and attacks the less substituted CH2 carbon in fashion. After work-up the product is 2-methylbutan-2-ol, CCC(C)(C)O.
Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on Epoxide and ether cleavage regiochemistry on drawn structures
Previous questionNext question

More questions on Epoxide and ether cleavage regiochemistry on drawn structures