Textbook Question
Predict the products of the following reactions.
(g)
24. Enolate Chemistry: Reactions at the Alpha-Carbon
Acetoacetic Ester Synthesis
2:16 minutesProblem 66c
Textbook Question
Indicate how each of the following compounds can be synthesized from the given starting material and any other necessary reagents:
c. 
Verified step by step guidance1
Step 1: Analyze the starting material and the target compound. The starting material is an ethyl acetoacetate derivative, and the target compound is a ketone with a cyclohexyl group attached. This suggests that a nucleophilic substitution followed by cyclization is required.
Step 2: Perform an alkylation reaction on the ethyl acetoacetate derivative. Use a suitable alkyl halide, such as bromocyclohexane, and a strong base like sodium ethoxide (NaOEt) to deprotonate the alpha-carbon of the starting material. This generates a nucleophilic enolate ion that can attack the alkyl halide, forming a new C-C bond.
Step 3: Hydrolyze the ester group in the alkylated product. Use acidic or basic hydrolysis conditions to convert the ester group into a carboxylic acid. This step prepares the molecule for decarboxylation.
Step 4: Decarboxylate the carboxylic acid under heating conditions. This step removes the carboxyl group, leaving behind the desired ketone structure with the cyclohexyl group attached.
Step 5: Purify the final product using appropriate techniques such as distillation or recrystallization to isolate the target ketone compound.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Acetoacetic Ester Synthesis
Acetoacetic ester synthesis is a method for forming ketones through the reaction of an acetoacetic ester with an alkyl halide. This process involves the enolate ion of the acetoacetic ester attacking the alkyl halide, leading to the formation of a new carbon-carbon bond. The resulting compound can then undergo hydrolysis and decarboxylation to yield a ketone.
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Enolate Chemistry
Enolates are reactive intermediates formed from the deprotonation of carbonyl compounds, such as esters or ketones. They are crucial in nucleophilic addition reactions, where they can act as nucleophiles to attack electrophiles. Understanding enolate stability and reactivity is essential for predicting the outcomes of reactions involving acetoacetic esters and other carbonyl compounds.
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Reagents and Reaction Conditions
The choice of reagents and reaction conditions significantly influences the outcome of organic reactions. In acetoacetic ester synthesis, common reagents include strong bases (like sodium ethoxide) for deprotonation and alkyl halides for alkylation. Additionally, controlling temperature and solvent can affect the reaction rate and selectivity, making it vital to understand these factors for successful synthesis.
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