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Question

Which of the compounds shown will react with dimethyl malonate in the presence of methoxide ion to give a compound, which on treatment with aqueous acid and gentle heating will decarboxylate to form butanoic acid?

A
CH2CHCH2COOH
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B
CH3CH2Br
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C
CH3CH2COCH3
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D
CH3CH2CH2Br
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Solution

The correct option is A CH3CH2Br
Butanoic Acid:
The compounds shown in the above reaction CH3CH2CH2Br react with dimethyl malonate in the presence of methoride ion to give a compound, which on treatment with aqueous acid and gentle heating will decarbonylate to form butanic acid.



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