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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 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: Treatment of ketone A with LDA followed by CH3CH2 did not form the desired alkylation product B. What product was formed instead? Devise a multistep method to convert A to B, a synthetic intermediate used to prepare the anticancer drug tamoxifen (Section 23.8C and the chapter-opening molecule).

Question: Which C-Hbonds in the following molecules are acidic because the resulting conjugate base is resonance stabilized?

Question: During the metabolism of glucose, glyceraldehyde 3-phosphate is converted to dihydroxyacetone phosphate by a process that involves two keto-enol tautomerizations. Draw a stepwise mechanism for this reaction in the presence of acid.

Question: Synthesize each compound from cyclohexanone and organic halides having ≤4 C’s. You may use any other inorganic reagents.

a.

b.

c.

Question:What alkyl halides are needed to prepare each ketone using the acetoacetic ester synthesis?
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