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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ro218

Which of the following statements about epoxidation of alkenes with mCPBA are correct?

  1. AThe oxygen transfer is concerted and stereospecific (syn).
  2. BA cis-alkene gives the cis-epoxide.
  3. CA trans-alkene gives the cis-epoxide.
  4. DElectron-rich alkenes react faster than electron-poor ones.

Answer: A, B, D

The peracid delivers oxygen to one face of the C=C in a single step, so alkene geometry is retained: cis gives cis and trans gives trans. The reaction is electrophilic, so more electron-rich alkenes react faster. Hence the statement that a trans-alkene gives a cis-epoxide is wrong.
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