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  Step 1: 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 which in further reaction with the alpha beta-unsaturated ketone the alkylation occur means the removal of hydrogen of the alkyl group attached at the alpha position to the carbonyl.

Decarboxylation

It is the reaction that 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.

 Aldol cyclisation 

It is the nucleophilic acyl substitution reaction of the carbonyl group forming the enolate ion which leads to the cyclisation with the carbonyl group in the molecule which leads to the formation of $\mathrm{\alpha },\mathrm{\beta }$ unsaturated ketone.

Mechanism

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

Mechanism