JEE Main · 2019 · 09 Apr 2019 · Shift 2 · Aldehydes Ketones and Carboxylic Acids

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In the following reaction

Carbonyl compound acetal
Rate of the reaction is the highest for:
  1. (A)Acetone as substrate and methanol in stoichiometric amount
  2. (B)Proponal as substrate and methanol in stoichiometric amount
  3. (C)Acetone as substrate and methanol in excess
  4. (D)Propanal as substrate and methanol in excess✓ Correct

Answer: (D)

Solution

Acetal formation is a nucleophilic addition at the carbonyl, and an aldehyde reacts faster than a ketone because its carbonyl carbon is less hindered and more electrophilic, whereas a ketone has two electron-donating alkyl groups shielding that carbon. So propanal, an aldehyde, outruns acetone, a ketone. On top of that the reaction is an equilibrium, so taking methanol in excess pushes it toward the acetal by Le Chatelier's principle. The fastest case therefore pairs propanal with methanol in excess.

JEE Main · 2019 · 09 Apr 2019 · Shift 2 · Single correct option

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