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NEET CHEMISTRYAlcohols, Phenols and EthersMedium

Question

Acetophenone when reacted with a base, C2H5ONaC_2H_5ONa, yields a stable compound which has the structure:

A

C6H5C(CH3)=CHCOC6H5C_6H_5-C(CH_3)=CH-CO-C_6H_5 (Dypnone)

B

C6H5CH=CHCOC6H5C_6H_5-CH=CH-CO-C_6H_5 (Chalcone)

C

C6H5COCH2CH(OH)C6H5C_6H_5-CO-CH_2-CH(OH)-C_6H_5

D

C6H5C(CH3)2COC6H5C_6H_5-C(CH_3)_2-CO-C_6H_5

Step-by-Step Solution

Acetophenone (C6H5COCH3C_6H_5COCH_3) possesses α\alpha-hydrogen atoms. In the presence of a base like sodium ethoxide (C2H5ONaC_2H_5ONa), it undergoes a self-condensation reaction known as Aldol Condensation.

  1. Enolate Formation: The base abstracts an α\alpha-proton from one molecule of acetophenone to form an enolate ion.
  2. Nucleophilic Attack: This enolate ion attacks the carbonyl carbon of another acetophenone molecule to form a β\beta-hydroxy ketone (aldol adduct).
  3. Dehydration: Due to the presence of the aromatic ring and the conjugation possibilities, the intermediate readily loses a water molecule (dehydration) to form a stable α,β\alpha,\beta-unsaturated ketone called Dypnone (1,3-diphenylbut-2-en-1-one).

Reaction: 2C6H5COCH3C2H5ONaC6H5C(CH3)=CHCOC6H5+H2O2C_6H_5COCH_3 \xrightarrow{C_2H_5ONa} C_6H_5-C(CH_3)=CH-CO-C_6H_5 + H_2O

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Alcohols, Phenols and Ethers. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYAlcohols, Phenols and Ethersacetophenonereactedyieldsstablecompound

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