1. NaOEt CO₂Et 2. H3O+ 3. heat Br H3C H₂C 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 H :Ö :OH OH OH CO2 Ба CH3 CH3
1. NaOEt CO₂Et 2. H3O+ 3. heat Br H3C H₂C 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 H :Ö :OH OH OH CO2 Ба CH3 CH3
Chapter17: Alcohols And Phenols
Section17.SE: Something Extra
Problem 71AP: A problem often encountered in the oxidation of primary alcohols to acids is that esters are...
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