CO₂Et 1. NaOEt 2. H₂O* 3. heat Br H3C H3C CO₂Et CO₂H + CO2 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 EtO₂C -H :OCH2CH3 HOCH2CH3 EtO₂C EtO₂C

CO₂Et 1. NaOEt 2. H₂O* 3. heat Br H3C H3C CO₂Et CO₂H + CO2 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 EtO₂C -H :OCH2CH3 HOCH2CH3 EtO₂C EtO₂C

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Section21.SE: Something Extra

Problem 75AP: One frequently used method for preparing methyl esters is by reaction of carboxylic acids with...

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