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Chapter 23: Q49. (page 924)

Question: Synthesize each compound from ethyl acetoacetate. You may use any other organic or inorganic reagents.

Short Answer

Expert verified

Answer

The compounds synthesized using the acetoacetic 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 into a ketone having one or two alkyl groups on the 伪-carbon. It is a 3-step process deprotonation reaction that takes place first, followed by alkylation with the alkylating agent, and the last step is hydrolysis and deprotonation.

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 a

Synthesis of b

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Most popular questions from this chapter

Question: Nabumetone is a pain reliever and anti-inflammatory agent sold under the brand name of Relafen.

a. Write out a synthesis of nabumetone from ethyl acetoacetate.

b. What ketone and alkyl halide are needed to synthesize nabumetone by direct enolate alkylation?

Question: Synthesize each compound from diethyl malonate. You may use any other organic or inorganic reagents.

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: Draw the organic products formed in each reaction

Question: Which carbonyl compound in each pair exhibits the higher percentage of the enol tautomer?
See all solutions

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