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Chapter 23: Q44. (page 924)

Question: Use the malonic ester synthesis to prepare each carboxylic acid.

Short Answer

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Answer

The starting materials needed to prepare each carboxylic acid by the malonic ester synthesis are shown below.

Step by step solution

01

Definition of acetoacetic ester reaction

The acetoacetic ester synthesis is a method required for the conversion of ethyl acetoacetate to a ketone having one or two alkyl groups on the α -carbon.

02

Retrosynthetic pathway for obtaining the starting materials

To obtain the starting materials, a retrosynthetic analysis is followed, as shown below.

03

Forward pathway for obtaining the product

To obtain the product, a forward reaction scheme analysis is followed, as shown below.

Synthesis of the given compound a.

Synthesis of the given compound b.

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Most popular questions from this chapter

Question:What cyclic product is formed from each dihalide using the malonic ester synthesis?

Question: Although ibuprofen is sold as a racemic mixture, only the S enantiomer acts as an analgesic. In the body, however, some of the R enantiomer is converted to the S isomer by tautomerization to an enol and then protonation to regenerate the carbonyl compound. Write a stepwise mechanism for this isomerization.

Question: Vitamin C is a stable enediol. Draw the structure of the two keto tautomers in equilibrium with the enediol and explain why the enediol is more stable than the other tautomer.

Question:Explain why each of the following carboxylic acids cannot be prepared by a malonic ester synthesis.

Question: The analgesic naproxen can be prepared by a stepwise reaction sequence from ester A. Using enolate alkylation in one step, what reagents are needed to convert A to naproxen? Write the structure of each intermediate. Explain why a racemic product is formed.
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