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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ro261

The ketone shown is treated with m-CPBA. Select ALL correct statements.

  1. AThe product is the ester in which the tert-butyl group is attached to the oxygen.
  2. BThe product is phenyl pivalate (the phenyl group is attached to the oxygen).
  3. CThe reaction goes through a tetrahedral Criegee intermediate formed by addition of the peroxyacid to the carbonyl group.
  4. DThe migrating group moves with retention of its configuration.

Answer: A, C, D

The compound is tert-butyl phenyl ketone (pivalophenone). Tertiary alkyl has a higher migratory aptitude than phenyl, so the product is tert-butyl benzoate (statement 1 true, statement 2 false). The mechanism proceeds through the Criegee intermediate and the migrating group moves with retention of configuration (both true).
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