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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ro220

Cyclohex-2-en-1-one reacts with and aqueous NaOH. Which statements are correct?

  1. AThe peroxide anion adds in a conjugate fashion to the enone.
  2. BThe product is 2,3-epoxycyclohexan-1-one.
  3. CThese conditions are generally unsuitable for epoxidising an unactivated alkene such as cyclohexene.
  4. DThe oxygen is transferred as an electrophilic oxygen from a peroxy acid.

Answer: A, B, C

Hydroperoxide anion is a nucleophile and adds to the beta carbon of the enone, then the enolate closes onto the O-O bond, expelling hydroxide, to form the epoxide. An unactivated alkene has no electrophilic carbon for this attack. The mechanism is nucleophilic, not an electrophilic transfer from a peracid.
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