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Chapter 22: Q54P (page 1193)

Show how an acetoacetic ester synthesis might be used to form a δ -diketone such as heptane-2,6-dione.

Short Answer

Expert verified

In Acetoacetic ester synthesis, beta-ketoester has the acidic hydrogen (presence of keto group on one side and ester group on another side) abstracted by the base, resulting in the formation of the enolate ion (resonance stabilize).

The enolate formed will act as anucleophilein many SN2 reactions, forming many organic compounds.

Step by step solution

01

Acetoacetic ester synthesis

In Acetoacetic ester synthesis, beta-ketoester has the acidic hydrogen (presence of keto group on one side and ester group on another side) abstracted by the base, resulting in the formation of the enolate ion (resonance stabilize).

The enolate formed will act as anucleophilein many SN2 reactions, forming many organic compounds.

02

Synthesis of heptane-2,6-dione

Ethyl 3-oxibutanoate reacts with ethoxide ion to form the enolate, which will attack in the but-3-en-2-one (1,4-addition), followed by acidic hydrolysis to form ethyl 2-acetyl-5-oxohexanoate by keto-enol tautomerism.

The ethyl 2-acetyl-5-oxohexanoate undergoes acidic hydrolysis and decarboxylation by heating forms the desired product heptane 2,6-dione.

Synthesis of Heptane 2,6-dione

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Most popular questions from this chapter

Show how you would accomplish the following conversions in good yields. You may use any necessary reagents.

Question:Show how you would use the Robinson annulation to synthesize the following compounds.

Question:Show how you would use an aldol, Claisen, or another type of condensation to make each compound

b.

Some (but not all) of the following keto esters can be formed by Dieckmann condensations. Determine which ones are possible, and draw the starting diesters.

Propose mechanisms for the two Dieckmann condensations just shown.
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