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CUET · CHEMISTRY · PYQ PAPER 2023

Read the following passage given below and answer the question.
Aldehydes and ketones undergo nucleophilic addition reactions. A nucleophile attacks the electrophilic carbon atom of polar carbonyl group from perpendicular to plane of \(sp^2\) hybridised orbitals of carbonyl carbon. The hybridisation of carbon changes from \(sp^2\) to \(sp^3\) and a tetrahedral alkoxide intermediate is formed. This captures \(H^+\) to give neutral product. In carboxylic acids, carbonyl carbon is less electrophilic than carbonyl carbon in aldehydes and ketones.
An organic compound \(C_3H_6O\) does not give a precipitate with 2,4-dinitrophenylhydrazine and also does not react with metallic sodium. It could be :

  1. A \(CH_3CH_2CHO\)
  2. B \(CH_2=CH-CH_2OH\)
  3. C \(CH_3COCH_3\)
  4. D \(CH_2 = CH – O – CH_3\)
Verified Solution

Answer & Solution

Correct Answer

(D) \(CH_2 = CH – O – CH_3\)

Step-by-step Solution

Detailed explanation

The compound does not react with 2,4-dinitrophenylhydrazine, meaning it is not an aldehyde or ketone. Eliminates \(CH_3CH_2CHO\) and \(CH_3COCH_3\). The compound does not react with metallic sodium, meaning it is not an alcohol. Eliminates \(CH_2=CH-CH_2OH\). The only remaining…
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