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JEE Main levelOne or more correct optionsDifficulty 2 of 3o1228

The ketone shown is treated with each reagent below, followed by aqueous work-up where needed. Select the reagent(s) that give a tertiary alcohol (an alcohol whose carbinol carbon is bonded to three other carbon atoms).

  1. A
  2. B
  3. C
  4. D

Answer: A, C, D

3-Methylbutan-2-one has a ketone carbonyl carbon bearing two carbon substituents. Adding a carbon nucleophile (methylmagnesium bromide, phenyllithium, or cyanide in the cyanohydrin reaction) creates a carbon bearing OH and three carbon groups, a tertiary alcohol. Sodium borohydride delivers hydride, giving a secondary alcohol.
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