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NEET CHEMISTRYMedium

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

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