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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ro217

Which of the following ketones give the ester shown as the major product on treatment with a peracid? (Migratory aptitude: tertiary alkyl secondary alkyl primary alkyl methyl.)

  1. A3,3-dimethylbutan-2-one gives tert-butyl ethanoate
  2. Bbutan-2-one gives ethyl ethanoate
  3. Cacetophenone gives methyl benzoate
  4. Dcyclobutanone gives gamma-butyrolactone (oxolan-2-one)

Answer: A, B, D

The group of higher migratory aptitude is the one bonded to oxygen in the ester. tert-Butyl beats methyl, and ethyl beats methyl. Cyclobutanone gives the five-membered lactone. Acetophenone gives phenyl ethanoate, as phenyl migrates in preference to methyl, so methyl benzoate is wrong.
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