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CUET · CHEMISTRY · PYQ PAPER 2023

Answer the question on the basis of passage given below:
Aldehydes are generally more reactive than ketones in nucleophilic addition reactions due to steric and electronic reasons. Sterically, the presence of two relatively large substituents in ketones hinders the approach of nucleophile to carbonyl carbon more than aldehydes having only one such substituent Electronically aldehydes are more reactive than ketones because two alkyl groups reduce the elctrophilicity of the carbonyl more effectively than in former.
4-Hydroxy-4-methylpentan-2-one and 4-methylpent-3-en-2-one are the products obtained from A by aldol
condensation. \(A\) is:

  1. A \(CH _3 COCH _3\)
  2. B \(CH _3 CHO\)
  3. C \(H _3 C - CH _2- CH _2- CH _2- CHO\)
  4. D \(H _3 C - CH _2- CH _2- CHO\)
Verified Solution

Answer & Solution

Correct Answer

(A) \(CH _3 COCH _3\)

Step-by-step Solution

Detailed explanation

\(A\) is formed by self-aldol condensation. \(2 \times CH_3COCH_3 \xrightarrow{\text{Aldol}} CH_3COCH_2C(OH)(CH_3)_2 \text{ (4-Hydroxy-4-methylpentan-2-one)} \xrightarrow{\text{-H}_2O} CH_3COCH=C(CH_3)_2 \text{ (4-methylpent-3-en-2-one)}\) \(A = CH_3COCH_3\)
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