Question

Predict the products of the following reactions.(i)

Accepted Answer

Step 1: Identify the reaction type. This is a Claisen condensation reaction followed by hydrolysis and decarboxylation. The Claisen condensation involves the reaction of an ester with a ketone in the presence of a base to form a β-keto ester intermediate. Step 2: Analyze the reactants. The first reactant is ethyl acetoacetate (CH₃COCH₂COOCH₂CH₃), which is an ester with an acidic α-hydrogen. The second reactant is cyclohexanone, a ketone with an α-hydrogen. The base used is sodium ethoxide (NaOCH₂CH₃), which will deprotonate the α-hydrogen of the ester to form an enolate ion. Step 3: Mechanism of the Claisen condensation. The enolate ion formed from ethyl acetoacetate will attack the carbonyl carbon of cyclohexanone, leading to the formation of a new C-C bond. This results in a β-keto ester intermediate after the elimination of the ethoxide ion. Step 4: Hydrolysis and decarboxylation. The β-keto ester intermediate undergoes hydrolysis in the presence of acid (H₃O⁺), converting the ester group into a carboxylic acid. Upon heating, the carboxylic acid undergoes decarboxylation, releasing CO₂ and forming the final product. Step 5: Predict the product structure. The final product will be a substituted cyclohexanone with the new substituent derived from the ethyl acetoacetate reactant. The exact structure can be determined by tracing the connectivity formed during the Claisen condensation and subsequent steps.

Predict the products of the following reactions.
(i)

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Concetti chiave

Reaction Mechanisms

Functional Groups

Stereochemistry