Question

Propose a mechanism for the following reaction. Show the structure of the compound that results from hydrolysis and decarboxylation of the product.

Short answer

Reaction Mechanism

Step-by-step solution

Step-by-Step SolutionStep1: Melonic ester synthesis

It’s a method in which substituted derivative of acetic acid is formation occur from dimethyl malonate in the presence of sodium ethoxide 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 enolate ion which on further reaction with the alkyl halide the alkylation occur means the by removal of halide ion the alkyl group attached at the alpha position to the carbonyl followed by decarboxylation the removal of carbon dioxide followed by hydrolysis by the removal of -OH group formation of alkene occurs.

Decarboxylation

It is the reaction which leads to the removal of the carbonyl group and releases carbon di-oxide $\mathbf{\left(}{\mathbf{CO}}_{\mathbf{2}}\mathbf{\right)}$. Decarboxylation occurs by providing heat in the reaction.

Mechanism

1. Acidic hydrogen protonated
2. Formation of the enolate ion
3. Alkylation
4. Decarboxylation, hydrolysis
5. Alkene formation

Reaction Mechanism