The acetoacetic ester synthesis is a carbonyl alkylation reaction. It is used to prepare methyl ketones from primary alkyl halides, lengthening the carbon chain by three atoms. Thus, the product can be visualized as being a "substituted acetone." 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. м Br H3C H3C OEt 1. NaOEt 2. H₂O* 3. heat H₂C. Draw curved arrows to show the movement of electrons in this step of the mechanism. CO₂ EtOH CH3 Arrow-pushing Instructions H3C 1:0: :0: :Br: Br: H₂C CH3 CH3 H3C CH3 7b

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Chapter1: Chemical Foundations
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The acetoacetic ester synthesis is a carbonyl alkylation reaction. It is used to prepare methyl ketones from primary alkyl halides, lengthening the carbon chain by three atoms. Thus, the product can be
visualized as being a "substituted acetone." 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.
м
Br
H3C
H3C
OEt
1. NaOEt
2. H₂O*
3. heat
H₂C.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
CO₂
EtOH
CH3
Arrow-pushing Instructions
H3C
1:0:
:0:
:Br:
Br:
H₂C
CH3
CH3
H3C
CH3
7b
Transcribed Image Text:The acetoacetic ester synthesis is a carbonyl alkylation reaction. It is used to prepare methyl ketones from primary alkyl halides, lengthening the carbon chain by three atoms. Thus, the product can be visualized as being a "substituted acetone." 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. м Br H3C H3C OEt 1. NaOEt 2. H₂O* 3. heat H₂C. Draw curved arrows to show the movement of electrons in this step of the mechanism. CO₂ EtOH CH3 Arrow-pushing Instructions H3C 1:0: :0: :Br: Br: H₂C CH3 CH3 H3C CH3 7b
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