(a)
Interpretation: The
Concept introduction: The Malonic ester synthesis is a method which is used to convert diethyl malonate into a carboxylic acid.
Answer to Problem 23.43P
The alkyl halide which is needed to prepare given carboxylic acid using the malonic ester synthesis is
Explanation of Solution
The given carboxylic acid is,
Figure 1
All alkyl groups on the alpha carbon will be obtained from alkyl halides and the remaining molecule is obtained from ethyl acetoacetate. Thus, for the required alkyl halide, the location of alpha carbon is shown below.
Figure 2
Hence, the alkyl halide which is needed to prepare given carboxylic acid using the malonic ester synthesis is
The reaction of diethylmalonate with
Figure 3
The mechanism involved in the given reaction as follows,
Base abstracts the proton from the alpha carbon and enolate ion reacts with
Figure 4
The alkyl halide which is needed to prepare given carboxylic acid using the malonic ester synthesis is
(b)
Interpretation: The alkyl halide which is needed to prepare given carboxylic acid using the malonic ester synthesis is to be predicted.
Concept introduction: The Malonic ester synthesis is a method which is used to convert diethyl malonate into a carboxylic acid.
Answer to Problem 23.43P
The alkyl halide which is needed to prepare given carboxylic acid using the malonic ester synthesis is
Explanation of Solution
The given carboxylic acid is,
Figure 5
All alkyl groups on the alpha carbon will be obtained from alkyl halides and the remaining molecule is obtained from ethyl acetoacetate. Thus, for the required alkyl halide, the location of alpha carbon is shown below.
Figure 6
Hence, the alkyl halide which is needed to prepare given carboxylic acid using the malonic ester synthesis is
The reaction of diethylmalonate with
Figure 7
The mechanism involved in the given reaction as follows,
Base abstracts the proton from the alpha carbon and enolate reacts with
Figure 8
The alkyl halide which is needed to prepare given carboxylic acid using the malonic ester synthesis is
(c)
Interpretation: The alkyl halide which is needed to prepare given carboxylic acid using the malonic ester synthesis is to be predicted.
Concept introduction: The Malonic ester synthesis is a method which is used to convert diethyl malonate into a carboxylic acid.
Answer to Problem 23.43P
The alkyl halide which is needed to prepare given carboxylic acid using the malonic ester synthesis is
Explanation of Solution
The given carboxylic acid is,
Figure 9
All alkyl groups on the alpha carbon will be obtained from alkyl halides and the remaining molecule is obtained from ethyl acetoacetate. Thus, for the required alkyl halide, the location of alpha carbon is shown below.
Figure 10
Hence, the alkyl halide which is needed to prepare given carboxylic acid using the malonic ester synthesis is
The reaction of diethylmalonate with
Figure 11
The mechanism involved in the given reaction as follows,
Base abstracts the proton from the alpha carbon and enolate reacts with
Figure 12
The alkyl halide which is needed to prepare given carboxylic acid using the malonic ester synthesis is
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Chapter 23 Solutions
Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning