The correct sequence of reactions that will convert diethylmalonate to the carbo

Question

The correct sequence of reactions that will convert diethylmalonate to the carboxylic acid shown below is __________ 1. NaoEt in EtoH, 2. 1, 4-dibromobutane, 3. NaoEt in EtoH, 4.aq. acid and heat 1. NaoEt in EtoH, 2. 1, 5-dibromopentane, 3. NaoEt in EtoH, 4. aq. acid and heat 1. NaoEt in EtoH, 2. 1, 1-dibromocyclopentane 3. NaoEt in EtoH, 4. aq. acid and heat 1. NaoEt in EtoH, 2. 1, 4-dibromobutane, 3. aq. acid and heat, 4. NaoEt in EtOH, 1. NaoEt in EtoH, 2. 1, 1-dibromobutane 3 NaoEt in EtoH, 4. aq. acid and heat

Explanation / Answer

The correct sequence of reagents for the formation of given compound starting with diethylmalonate would be,

A :

First formation of enolate by NaOEt in EtOH, alkylation by using 1,4-dibromobutane. asecond enolate is generated and intramolecular alkylation to form 5-membered ring is formed. Hydrolysis and decarboxylation under acidic medium gives the desired compound.

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