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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**Understanding Self-Claisen Condensation**
**Problem:**
5. Give the expected product of the following self-Claisen condensation.
**Reaction:**
\[ \text{2 CH}_3\text{CH}_2\text{CH}_2\text{O}\text{C}\left( \text{O} \right)\text{CH}_2\text{CH}_3 \xrightarrow{\text{1) Na}^+\text{-OCH}_2\text{CH}_3 \quad \text{2) H}_3\text{O}^+ \text{to pH 5}} \]
**Answer:**
The structure of the product is not provided in the image, but here is the mechanism:
**Mechanism Breakdown:**
1. **Formation of Enolate Ion:**
- The first step involves the deprotonation of the α-hydrogen of the ester by ethoxide ion (Na+ -OEt), resulting in the formation of an enolate ion.
2. **Nucleophilic Attack:**
- The enolate ion then performs a nucleophilic attack on the carbonyl carbon of a second molecule of the ester, creating a tetrahedral alkoxide intermediate.
3. **Reformation of Carbonyl and Departure of Ethoxide:**
- This alkoxide intermediate then collapses back into the carbonyl form, ejecting the ethoxide group (-OEt) which was initially added.
4. **Protonation:**
- The final step involves the acidification (using H3O+ to pH 5) of the resulting β-keto ester to neutralize the intermediate.
**Products:**
- Resulting in a β-keto ester and ethanol (EtOH).
### Summary of the reaction:
\[ \text{2 CH}_3\text{CH}_2\text{CH}_2\text{O}\text{C}\left( \text{O} \right)\text{CH}_2\text{CH}_3 \xrightarrow{\text{1) Na}^+\text{-OCH}_2\text{CH}_3 \quad \text{2) H}_3\text{O}^+ \text{to pH 5}} \text{Product (β-Keto Ester)} + \text{CH}_3\text{CH}_2\text{OH} \]
Note](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fff015db4-0da8-42fc-9d60-01a672218c35%2F93b3b6fa-7de8-46ac-9260-17adf884e256%2F83my3k_processed.jpeg&w=3840&q=75)
Transcribed Image Text:---
**Understanding Self-Claisen Condensation**
**Problem:**
5. Give the expected product of the following self-Claisen condensation.
**Reaction:**
\[ \text{2 CH}_3\text{CH}_2\text{CH}_2\text{O}\text{C}\left( \text{O} \right)\text{CH}_2\text{CH}_3 \xrightarrow{\text{1) Na}^+\text{-OCH}_2\text{CH}_3 \quad \text{2) H}_3\text{O}^+ \text{to pH 5}} \]
**Answer:**
The structure of the product is not provided in the image, but here is the mechanism:
**Mechanism Breakdown:**
1. **Formation of Enolate Ion:**
- The first step involves the deprotonation of the α-hydrogen of the ester by ethoxide ion (Na+ -OEt), resulting in the formation of an enolate ion.
2. **Nucleophilic Attack:**
- The enolate ion then performs a nucleophilic attack on the carbonyl carbon of a second molecule of the ester, creating a tetrahedral alkoxide intermediate.
3. **Reformation of Carbonyl and Departure of Ethoxide:**
- This alkoxide intermediate then collapses back into the carbonyl form, ejecting the ethoxide group (-OEt) which was initially added.
4. **Protonation:**
- The final step involves the acidification (using H3O+ to pH 5) of the resulting β-keto ester to neutralize the intermediate.
**Products:**
- Resulting in a β-keto ester and ethanol (EtOH).
### Summary of the reaction:
\[ \text{2 CH}_3\text{CH}_2\text{CH}_2\text{O}\text{C}\left( \text{O} \right)\text{CH}_2\text{CH}_3 \xrightarrow{\text{1) Na}^+\text{-OCH}_2\text{CH}_3 \quad \text{2) H}_3\text{O}^+ \text{to pH 5}} \text{Product (β-Keto Ester)} + \text{CH}_3\text{CH}_2\text{OH} \]
Note
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