Illustrate the Background for the Malonic Ester Synthesis ?

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Illustrate the Background for the Malonic Ester Synthesis ?

Expert Solution
Step 1

Esters are the organic compounds having two oxygen atoms, one is doubly bonded to the carbon-atom known as carbonyl oxygen and the other one is linked by a single bond to the same carbon-atom.

The general formula of an ester is RCOOR represented as:

              Chemistry homework question answer, step 1, image 1

Malonic ester synthesis reaction involves different steps to synthesize substituted carboxylic acids. 

Step 2

The reaction starts with the reactant malonic acid. The reaction steps are shown below as:

1. One of the acidic hydrogen-atoms is removed by the base to give a carbanion which is resonance stabilized and forms an enolate ion.

                 Chemistry homework question answer, step 2, image 1

2. Since, the carbanion is high in electron density, it acts as a nucleophile and in the next step SN2 reaction takes place between the carbanion and the alkyl halide.

                 Chemistry homework question answer, step 2, image 2

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