Reaction of diethyl acetamidomalonate with sodium ethoxide to form enolate anion 1; The enolate anion acts as a nucleophile in an SN2 reaction with alkyl iodide 2 to form alkylated intermediate 2; Heating in the presence of aqueous acid hydrolyzes both the ester and the amide bonds, and induces decarboxylation to form alanine. Draw the structure of enolate anion 1.

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
Chapter18: Carboxylic Acids
Section: Chapter Questions
Problem 18.54P
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Amino acids can be prepared by the reaction of alkyl halides with diethyl acetamidomalonate, followed by heating the initial alkylation product with aqueous HCl. The reaction to form alanine involves the following steps:

  1. Reaction of diethyl acetamidomalonate with sodium ethoxide to form enolate anion 1;
  2. The enolate anion acts as a nucleophile in an SN2 reaction with alkyl iodide 2 to form alkylated intermediate 2;
  3. Heating in the presence of aqueous acid hydrolyzes both the ester and the amide bonds, and induces decarboxylation to form alanine.

Draw the structure of enolate anion 1.

O H
||
CH3CNHCCO₂CH₂CH3
co₂
CO,CH,CH3
diethyl acetamidomalonate
H₂NCHCOH
CH3
alanine
Transcribed Image Text:O H || CH3CNHCCO₂CH₂CH3 co₂ CO,CH,CH3 diethyl acetamidomalonate H₂NCHCOH CH3 alanine
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