The missing reagent in the sequence of synthesis shown is :
A
bromocyclopentane
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B
1,5-dibromopentane
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C
1,4-dibromobutane
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D
1,1-dibromocyclopentane
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Solution
The correct option is B1,4-dibromobutane
The active methylene group of diethyl malonate is deprotonated by using a strong base sodium ethoxide and alkylated with 1,4-dibromobutane to obtain diethyl cyclopentane-1,1-dicarboxylate.
The ester groups are hydrolyzed in alkaline medium followed by acid hydrolysis of salt to obtain dicarboxylic acid which on heating undergoes decarboxylation.