MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms III: Nucleophilic Substitution / Reactions of ethers and epoxides
JEE Main levelSingle correct optionDifficulty 2 of 3o3196

(Z)-But-2-ene is treated with in dichloromethane. The product is

  1. Acis-2,3-dimethyloxirane, a single achiral meso compound
  2. Bracemic trans-2,3-dimethyloxirane, i.e. and
  3. Conly -2,3-dimethyloxirane
  4. Dmeso-butane-2,3-diol

Answer: A

Epoxidation with a peroxy acid is a syn addition of oxygen, so the geometry of the alkene is retained: the two methyl groups of the (Z)-alkene stay cis on the ring. cis-2,3-Dimethyloxirane has a mirror plane and is , i.e. meso. The diol does not form in the absence of water and acid.
Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on Reactions of ethers and epoxides

More questions on Reactions of ethers and epoxides