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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ap018

Ethyl methanoate () is treated with excess in dry ether and then with . Which of the following are formed?

  1. Apropan-2-ol
  2. Bethanol
  3. C2-methylpropan-2-ol
  4. Dethanal

Answer: A, B

The first displaces ethoxide to give ethanal, which immediately adds a second to give , hydrolysed to propan-2-ol (secondary). The leaving ethoxide gives ethanol on work-up. No tertiary alcohol forms because the intermediate is an aldehyde, not a ketone.
Practice Alcohols, Phenols and Ethers More on Preparation of alcohols including from carbonyls and Grignard

More questions on Preparation of alcohols including from carbonyls and Grignard