Question

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

Short answer

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 S_N2 reactions, forming many organic compounds.

Step-by-step solution

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 S_N2 reactions, forming many organic compounds.

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