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Question

Malonic ester contains an active methylene group and two hydrogen atoms of active methylene group are easily replaced by alkyl and acyl groups in the presence of strong base. The carbonation intermediate formed, makes SN2 attack on alkyl or acyl groups.
Which of the following is formed as the final product in the sequences of reaction?

44856_b37c91fda9dc4c5d82d8519255aff97c.png

A
C6H5COC|HCH3COOH
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B
C6H5COCH2CH2COOH
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C
C6H5COCH2CH2CH3
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D
C6H5COCH2CH3
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Solution

The correct option is D C6H5COCH2CH3
In presence of sodium ethoxide, the malonic ester is deprotonated to form a carboanion which attacks benzoyl chloride to form intermediate (N). The ester groups are hydrolyzed to carboxylic acids to give intermediate (Q). On heating, decarboxylation gives product (P) which is propiophenone.
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