
(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
ORGANIC CHEMISTRY
- Name the major organic product of the following action of 4-chloro-4-methyl-1-pentanol in neutral pollution 10+ Now the product. The product has a molecular formula f b. In a singly hain, the starting, material again converts into a secule with the molecular kormula CIO. but with comply Draw the major organic structure inhalationarrow_forwardMacmillan Learning Alcohols can be oxidized by chromic acid derivatives. One such reagent is pyridinium chlorochromate, (C,H,NH*)(CICTO3), commonly known as PCC. Draw the proposed (neutral) intermediate and the organic product in the oxidation of 1-butanol by PCC when carried out in an anhydrous solvent such as CH₂C₁₂. PCC Intermediate OH CH2Cl2 Draw the intermediate. Select Draw Templates More с H Cr о Product Draw the product. Erase Select Draw Templates More H о Erasearrow_forwardIf I have 1-bromopropene, to obtain compound A, I have to add NaOH and another compound. Indicate which compound that would be. A C6H5 CH3arrow_forward
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
