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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hx089

Ethyl ethanoate is treated with excess in dry ether and then with . Select the correct statements.

  1. APropan-2-ol is the final product.
  2. BPropanone can be isolated as the major product because ketones are less reactive than esters toward Grignard reagents.
  3. C2-Methylpropan-2-ol is formed.
  4. DEthanol is also formed.

Answer: C, D

The first equivalent of adds to the ester and expels , giving propanone. Ketones are more reactive than esters, so a second equivalent adds at once to give . After hydrolysis, 2-methylpropan-2-ol (tertiary) and ethanol are obtained. Propanone cannot be isolated and propan-2-ol would need a hydride, not a methyl, nucleophile.
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