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Chapter 22: Q54P (page 1193)

Show how an acetoacetic ester synthesis might be used to form a 未 -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

Question: Predict the products of the following reactions

d.

Without looking back, propose a mechanism for the hydrolysis of this iminium salt to the alkylated ketone. The first step is attack by water, followed by loss of a proton to give a carbinolamine. Protonation on nitrogen allows pyrrolidine to leave, giving the protonated ketone.

Show how cyclohexanone might be converted to the following 未- diketone .

The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts with an aldehyde or ketone, in the presence of a secondary amine as a basic catalyst, to produce a new C=C. Show the starting materials that made each of these by a Knoevenagel condensation.

The following compound results from base-catalyzed aldol cyclization of a 2-substituted cyclohexanone.

  1. Show the diketone that would cyclize to give this product.
  2. Propose a mechanism for the cyclization
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