A variation of the acetamidomalonate synthesis can be used to synthesize serine. The process involves the following steps:Ethoxide ion deprotonates diethyl acetamidomalonate, forming enolate anion 1;Enolate anion 1 makes a nucleophilic attack on formaldehyde, forming tetrahedral intermediate 2;Protonation of the oxyanion forms alcohol 3;Acid hydrolysis yields dicarboxyamino alcohol 4;Decarboxylation leads to the final amino acid.Write out the mechanism on a separate sheet of paper, and then draw the structure of tetrahedral intermediate 2.You do not have to consider stereochemistry.You do not have to explicitly draw H atoms.Do not include lone pairs in your answer. They will not be considered in the grading.Draw carboxyl and amino groups in their uncharged forms.

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Answered: A variation of the acetamidomalonate…

Introduction to General, Organic and Biochemistry

11th Edition

ISBN:9781285869759

Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Chapter19: Carboxylic Anhydrides, Esters, And Amides

Section: Chapter Questions

Problem 19.25P

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A variation of the acetamidomalonate synthesis can be used to synthesize serine. The process involves the following steps:

Ethoxide ion deprotonates diethyl acetamidomalonate, forming enolate anion 1;
Enolate anion 1 makes a nucleophilic attack on formaldehyde, forming tetrahedral intermediate 2;
Protonation of the oxyanion forms alcohol 3;
Acid hydrolysis yields dicarboxyamino alcohol 4;
Decarboxylation leads to the final amino acid.

Write out the mechanism on a separate sheet of paper, and then draw the structure of tetrahedral intermediate 2.

You do not have to consider stereochemistry.
You do not have to explicitly draw H atoms.
Do not include lone pairs in your answer. They will not be considered in the grading.
Draw carboxyl and amino groups in their uncharged forms.

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