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Chapter 23: Q44. (page 924)

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

Short Answer

Expert verified

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 伪 -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: Treatment of ethyl acetoacetate with NaOEt (2 equiv) and BrCH2CH2Brforms compound X. This reaction is the first step in the synthesis of illudin-S, an antitumor substance isolated from thejack-o鈥�-lantern, a poisonous, saffron-colored mushroom. What is the structure of X?

Question: What enolate is formed when each ketone is treated with LDA in THF solution? What enolate is formed when these same ketones are treated with NaOCH3in CH3OHsolution?

Question:The enolate derived from diethyl malonate reacts with a variety of electrophiles (not just alkyl halides) to form new carbon-carbon bonds. With this in mind, draw the products formed when Na+ 鈥�CH(CO2Et)2 reacts with each electrophile, followed by treatment with H2O.

Question: Synthesize each compound from cyclohexanone and organic halides having 鈮�4 C鈥檚. You may use any other inorganic reagents.

a.

b.

c.

Question: Synthesize (Z)-hept-5-en-2-one from ethyl acetoacetate (CH3COCH2CO2Et ) and the given starting material. You may also use any other organic compounds or required inorganic reagents.
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