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Chapter 19: Problem 4

Show the product of Claisen condensation of ethyl 3-methylbutanoate in the presence of sodium ethoxide followed by acidification with aqueous HCl.

Short Answer

Expert verified
Answer: The product of Claisen condensation of ethyl 3-methylbutanoate in the presence of sodium ethoxide is an alpha, beta-unsaturated carbonyl compound with the structure CH_3CH_2CH(CH_3)C(O)CH_2CH_3.

Step by step solution

01

Step 1. Formation of the intermediate using sodium ethoxide

In this step, the ester ethyl 3-methylbutanoate (with the formula CH_3CH_2CH(CH_3)COOCH_2CH_3) reacts with sodium ethoxide (C_2H_5ONa). The ethoxide anion acts as a nucleophile and attacks the carbonyl carbon of the ester, followed by alkoxide ion elimination. The intermediate formed is alkoxide ion with alpha, beta-unsaturated carbonyl group. The equation for this step is: Ethyl 3-methylbutanoate + Sodium ethoxide -> Alkoxide ion (intermediate)
02

Step 2. Acidification of the intermediate using aqueous HCl

In this step, the intermediate from step 1 reacts with aqueous HCl. The proton (H^+) from the HCl reacts with the alkoxide ion to form a neutral molecule. The final product is formed in this step. The equation for this step is: Alkoxide ion (intermediate) + HCl -> Acidified product (final product)
03

Step 3. Identify the final product

After combining step 1 and step 2, the final product can be identified as the Claisen condensation product of the ester. The final product is an alpha, beta-unsaturated carbonyl group with a structure of CH_3CH_2CH(CH_3)C(O)CH_2CH_3.

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Most popular questions from this chapter

In 1887 , the Russian chemist Sergei Reformatsky at the University of Kiev discovered that treatment of an \(\alpha\)-haloester with zinc metal in the presence of an aldehyde or ketone followed by hydrolysis in aqueous acid results in formation of a \(\beta\)-hydroxyester. This reaction is similar to a Grignard reaction in that a key intermediate is an organometallic compound, in this case a zinc salt of an ester enolate anion. Grignard reagents, however, are so reactive that they undergo selfcondensation with the ester. Show how a Reformatsky reaction can be used to synthesize these compounds from an aldehyde or ketone and an \(\alpha\)-haloester.

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