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Chapter 19: Problem 30

When a 1:1 mixture of ethyl propanoate and ethyl butanoate is treated with sodium ethoxide, four Claisen condensation products are possible. Draw a structural formula for each product.

Short Answer

Expert verified
Answer: The structural formulas for the four possible Claisen condensation products are: 1. CH3CH2COOCH2CH2COCH2CH3 2. CH3CH2CH2COOCH2CH2COCH2CH3 3. CH3CH2COO(CH2)2CH2COCH2CH3 4. CH3CH2CH2COO(CH2)2CH2COCH2CH3

Step by step solution

01

Identify the esters and the strong base used in the reaction

The given esters are ethyl propanoate and ethyl butanoate, and the strong base is sodium ethoxide. Ethyl propanoate has the structure CH3CH2COOCH2CH3 and ethyl butanoate has the structure CH3CH2CH2COOCH2CH3.
02

Identify the nucleophilic sites in the ester molecules

In a Claisen condensation, the alpha-carbon (carbon next to the carbonyl carbon) of an ester is the nucleophile. In ethyl propanoate, the alpha-carbon is CH2 next to the carbonyl group, and in ethyl butanoate, it is also a CH2 next to the carbonyl group.
03

Combine the esters in all possible ways to form Claisen condensation products

We have four possible combinations of the alpha-carbons and carbonyl groups: 1. Ethyl propanoate alpha-carbon with ethyl propanoate carbonyl group 2. Ethyl propanoate alpha-carbon with ethyl butanoate carbonyl group 3. Ethyl butanoate alpha-carbon with ethyl propanoate carbonyl group 4. Ethyl butanoate alpha-carbon with ethyl butanoate carbonyl group We will draw the products of these combinations.
04

Draw the Claisen condensation products

Here are the structural formulas for the four Claisen condensation products: 1. Ethyl propanoate alpha-carbon with ethyl propanoate carbonyl group: Product 1: CH3CH2COOCH2CH2COCH2CH3 2. Ethyl propanoate alpha-carbon with ethyl butanoate carbonyl group: Product 2: CH3CH2CH2COOCH2CH2COCH2CH3 3. Ethyl butanoate alpha-carbon with ethyl propanoate carbonyl group: Product 3: CH3CH2COO(CH2)2CH2COCH2CH3 4. Ethyl butanoate alpha-carbon with ethyl butanoate carbonyl group: Product 4: CH3CH2CH2COO(CH2)2CH2COCH2CH3 These are the four possible Claisen condensation products when a 1:1 mixture of ethyl propanoate and ethyl butanoate is treated with sodium ethoxide.

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