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

Verified step by step guidance

1. Step 1: Understand the acetoacetic ester synthesis. This reaction involves the alkylation of ethyl acetoacetate (a β-keto ester) followed by hydrolysis and decarboxylation to form a substituted ketone. The general steps include enolate formation, alkylation, hydrolysis, and decarboxylation.
2. Step 2: Analyze the target compound for each part (a), (b), and (c). Determine the structure of the desired ketone and identify the alkyl group(s) that need to be introduced to the acetoacetic ester.
3. Step 3: For each compound, write the retrosynthetic analysis. Break down the target ketone into the corresponding β-keto ester and the alkyl halide(s) that would be used for alkylation. This step helps you plan the synthesis.
4. Step 4: Outline the forward synthesis for each compound. Start with ethyl acetoacetate, deprotonate it using a base (e.g., NaOEt) to form the enolate, and then perform the alkylation using the appropriate alkyl halide. If multiple alkylations are needed, repeat the process with a second alkyl halide.
5. Step 5: After alkylation, hydrolyze the ester group using aqueous acid or base to form the β-keto acid. Finally, heat the β-keto acid to induce decarboxylation, yielding the desired ketone. Repeat this process for each compound (a), (b), and (c).

Key Concepts

Acetoacetic Ester Synthesis

Acetoacetic ester synthesis is a method for synthesizing ketones through the reaction of an acetoacetic ester with an alkyl halide. This process involves the formation of a nucleophile from the acetoacetic ester, which then undergoes alkylation. The resulting product can be hydrolyzed and decarboxylated to yield a ketone. Understanding this synthesis is crucial for manipulating carbon chains and functional groups in organic compounds.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophile, resulting in the replacement of a leaving group. In the context of acetoacetic ester synthesis, the nucleophile generated from the acetoacetic ester attacks the alkyl halide. This concept is essential for predicting the outcome of reactions and understanding how different substituents can affect reactivity and product formation.

Decarboxylation

Decarboxylation is the process of removing a carboxyl group from a molecule, typically releasing carbon dioxide. In the acetoacetic ester synthesis, after the formation of the ketone, decarboxylation can occur to yield a more stable product. This reaction is significant in organic synthesis as it allows for the formation of simpler molecules from more complex precursors, often leading to the desired final products in synthetic pathways.