1. NaOEt CO₂Et 2. H3O+ 3. heat Br H3C H₁C CO₂Et CO₂H CO2 + EtOH The malonic ester synthesis is a carbonyl alkylation reaction. It is used to prepare carboxylic acids from primary alkyl halides, lengthening the carbon chain by two atoms. Thus, the product can be visualized as being a "substituted acetic acid." The reaction consists of three steps: generation of the enolate anion followed by SN2 reaction with a primary alkyl halide, ester hydrolysis under acid conditions, and decarboxylation. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions EtO₂C X ¯:0: :0: Br: EtO₂C. Br CH3 H3C CH3 CH3 56
1. NaOEt CO₂Et 2. H3O+ 3. heat Br H3C H₁C CO₂Et CO₂H CO2 + EtOH The malonic ester synthesis is a carbonyl alkylation reaction. It is used to prepare carboxylic acids from primary alkyl halides, lengthening the carbon chain by two atoms. Thus, the product can be visualized as being a "substituted acetic acid." The reaction consists of three steps: generation of the enolate anion followed by SN2 reaction with a primary alkyl halide, ester hydrolysis under acid conditions, and decarboxylation. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions EtO₂C X ¯:0: :0: Br: EtO₂C. Br CH3 H3C CH3 CH3 56
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Transcribed Image Text:1. NaOEt
CO₂Et
2. H3O+
3. heat
Br
H3C
H₁C
CO₂Et
CO₂H
CO2
+
EtOH
The malonic ester synthesis is a carbonyl alkylation reaction. It is used to prepare carboxylic acids from primary alkyl halides, lengthening the carbon chain by two atoms. Thus, the product can be
visualized as being a "substituted acetic acid." The reaction consists of three steps: generation of the enolate anion followed by SN2 reaction with a primary alkyl halide, ester hydrolysis under acid
conditions, and decarboxylation.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
EtO₂C
X
¯:0:
:0:
Br:
EtO₂C.
Br
CH3 H3C
CH3
CH3
56
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