Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Transcribed Image Text:**Title: Understanding Mixed Claisen Ester Condensation**
**Objective:**
Learn how to draw the most stable form of the major mixed Claisen product formed in the given reaction.
**Reaction Overview:**
- **Reactants:**
- Two esters, a propionate ester and an ethyl acetate.
- **Reagents:**
1. Sodium ethoxide (NaOC₂H₅)
2. Acidic workup (H₃O⁺)
- **Solvent:** Ethanol (C₂H₅OH)
**Mechanism Explanation:**
1. **Deprotonation:**
Sodium ethoxide (NaOC₂H₅) deprotonates the alpha-hydrogen of one of the esters, forming an enolate ion.
2. **Nucleophilic Attack:**
The enolate ion attacks the carbonyl carbon of the other ester, leading to the formation of a β-keto ester intermediate.
3. **Protonation:**
Acidic workup (H₃O⁺) protonates the alkoxide intermediate, resulting in the stable Claisen condensation product.
**Structural Insight:**
- Both ester groups participate in the reaction, but the more substituted enolate is typically favored in mixed Claisen reactions.
- The major product is a β-keto ester.
**Key Learning Points:**
- Recognize how mixed Claisen condensations form key carbon-carbon bonds.
- Understand the role of each reagent and solvent in the mechanism.
- Predict the structure of the Claisen product by considering enolate formation and nucleophilic acyl substitution.
This reaction is integral in organic synthesis, providing a pathway to create complex molecules from simple ester precursors. Understanding this process aids in mastering broader synthetic strategies in chemistry.
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