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.
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.
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter10: Alcohols
Section: Chapter Questions
Problem 10.58P
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Question
Amino acids can be prepared by the reaction of
- 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.
![O H
||
CH3CNHCCO₂CH₂CH3
co₂
CO,CH,CH3
diethyl acetamidomalonate
H₂NCHCOH
CH3
alanine](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F01cb39d3-0dee-4626-99d8-2f4c210e5aab%2Fbd15d9ba-be9d-451c-8fda-367486a02c9a%2Fxt9iwvu_processed.png&w=3840&q=75)
Transcribed Image Text:O H
||
CH3CNHCCO₂CH₂CH3
co₂
CO,CH,CH3
diethyl acetamidomalonate
H₂NCHCOH
CH3
alanine
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