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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

Organic Chemistry
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
Chapter7: Alkynes
Section: Chapter Questions
Problem 7.26P
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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
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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