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JEE Main · 2021 · 22 Jul 2021 · Shift 2 · Alcohols Phenols and Ethers

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Which one of the following compounds will provide a tertiary alcohol on reaction with excess of followed by hydrolysis?
  1. (A)(see structure)
  2. (B)(see structure)
  3. (C)(see structure)
    ✓ Correct
  4. (D)(see structure)

Answer: (C)

Solution

A Grignard reagent attacks an ester twice: the first addition expels the alkoxide and leaves a ketone, and the second adds to that ketone, so hydrolysis delivers an alcohol carrying two alkyl groups from the reagent. Phenyl acetate, , therefore picks up two methyl groups at the acetyl carbon and gives 2-methylpropan-2-ol. A nitrile, by contrast, adds the reagent once and stops at a ketone on hydrolysis, so it cannot reach a tertiary alcohol. The compound that provides a tertiary alcohol is the ester phenyl acetate, the product being 2-methylpropan-2-ol.

JEE Main · 2021 · 22 Jul 2021 · Shift 2 · Single correct option

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