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JEE Main levelSingle correct optionDifficulty 2 of 3ro209

2-Methylhepta-2,6-diene, , reacts with exactly one equivalent of mCPBA at low temperature. The major product is

  1. Athe bis-epoxide only
  2. Ba 1:1 mixture of the two mono-epoxides
  3. Cthe epoxide of the trisubstituted C=C: 2,2-dimethyl-3-(but-3-en-1-yl)oxirane
  4. Dthe epoxide of the terminal C=C: 2-(4-methylpent-3-en-1-yl)oxirane

Answer: C

Epoxidation by a peroxy acid is an electrophilic oxygen transfer, so it is faster at the more electron-rich, more substituted double bond. The trisubstituted alkene reacts much faster than the monosubstituted terminal one, so with one equivalent it is the major site.
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