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Draw the most stable form of the major product in the following reaction

Chemistry Dec 29, 2020

Draw the most stable form of the major product in the following reaction. 
0 1. Na0C2 2 zNAO'N 2. 1430. C2H5OH 
 

Expert Solution

1.Explanation | Common mistakes | Hint for next step

The base abstracts the alpha hydrogen of ester, which forms a carbanion. The carbanion donates its electrons to form a highly resonance-stabilized enolate, anion. The enolates are very strong nucleophiles.

2.Explanation | Common mistakes | Hint for next step

The enolates are very strong nucleophiles, and the carbon of ester carbonyls are very strong electrophiles by nature. Hence, the nucleophilic carbon from the ester enolate, attacks the electrophilic carbonyl carbon, which gives a condensed product.

3.Explanation

The reaction of alkoxide with hydronium ion gives beta-ketoester with alcohol, and water molecules as side products. Ethanol is a solvent that is used in this reaction, which does not involve in the reaction mechanism.

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