Question

Show how you would use the acetoacetic ester synthesis to make the following compounds

Short answer

It’s a method in which a substituted derivative of acetone formation occurs in the presence of sodium ethoxide from ethyl acetoacetate, followed by alkylation or acylation, then hydrolysis followed by decarboxylation to form a derivate of acetic acid as a product.

Step-by-step solution

Step-by-Step Solution  Step1: Acetoacetic ester synthesis

It’s a method in which a substituted derivative of acetone formation occurs in the presence of sodium ethoxide from ethyl acetoacetate, followed by alkylation or acylation, then hydrolysis followed by decarboxylation to form a derivate of acetic acid as a product.

Reaction followed by alkylation

Ethoxide is used as a base to form an enolate ion. In further reaction with the alkyl halide, the alkylation occurs means the removal of the halide ion, the alkyl group attached at the alpha position to the carbonyl.

Decarboxylation

The reaction leads to the removal of the carbonyl group and the release of carbon di-oxide$\left({\mathrm{CO}}_2\right)$.Decarboxylation occurs by providing heat in the reaction.

Formation of product

As per the formation of the desired product, the alkylation occurs twice, followed by the sodium ethoxide; then decarboxylation occurs to form the desired product.

Mechanism

1. Acidic hydrogen protonated
2. Formation of the enolate ion
3. Alkylation
4. Formation of again enolate ion
5. Alkylation again
6. Decarboxylation
7. Derivative of acetone

Mechanism