V. In the following reaction: CH3CH₂Br + CH3COOK → CH3COOCH₂CH3 +KBr Adding a small amount of sodium iodide increases the reaction rate significantly. Please using the reaction mechanisms, nucleophilicity and leaving group quality to explain.
V. In the following reaction: CH3CH₂Br + CH3COOK → CH3COOCH₂CH3 +KBr Adding a small amount of sodium iodide increases the reaction rate significantly. Please using the reaction mechanisms, nucleophilicity and leaving group quality to explain.
Chemistry
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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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### Reaction Analysis
**Reaction:**
\[ \text{CH}_3\text{CH}_2\text{Br} + \text{CH}_3\text{COOK} \rightarrow \text{CH}_3\text{COOCH}_2\text{CH}_3 + \text{KBr} \]
Adding a small amount of sodium iodide increases the reaction rate significantly. Please use reaction mechanisms, nucleophilicity, and leaving group quality to explain.
**Explanation:**
This reaction involves the conversion of an alkyl bromide (\(\text{CH}_3\text{CH}_2\text{Br}\)) and potassium acetate (\(\text{CH}_3\text{COOK}\)) to form an ester (\(\text{CH}_3\text{COOCH}_2\text{CH}_3\)) and potassium bromide (\(\text{KBr}\)).
1. **Nucleophilicity:**
- In this context, sodium iodide plays a critical role by enhancing the nucleophilicity of the reaction. Iodide ions (\(I^-\)) are better nucleophiles compared to bromide ions (\(Br^-\)) due to their larger size and higher polarizability.
2. **Leaving Group Quality:**
- The iodide ion can replace the bromide ion in the reaction, forming an alkyl iodide intermediate. This is because iodide is a better leaving group, which allows the reaction to proceed faster.
3. **Mechanism:**
- The substitution mechanism likely follows a \(S_N2\) pathway, where the iodide ion first substitutes the bromide, enhancing the overall reactivity and allowing the acetate ion to perform nucleophilic attack more efficiently.
The addition of sodium iodide, therefore, facilitates a faster reaction by improving the quality of the leaving group and enhancing the nucleophilicity of the anion responsible for the reaction.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F304a4b2a-88fb-410b-8fb9-f685a46fb6ee%2Fb13974ea-5d66-420a-8d55-392f4f69779c%2Fu4d4sfw_processed.jpeg&w=3840&q=75)
Transcribed Image Text:Certainly! Here's the transcription and explanation for an educational website:
---
### Reaction Analysis
**Reaction:**
\[ \text{CH}_3\text{CH}_2\text{Br} + \text{CH}_3\text{COOK} \rightarrow \text{CH}_3\text{COOCH}_2\text{CH}_3 + \text{KBr} \]
Adding a small amount of sodium iodide increases the reaction rate significantly. Please use reaction mechanisms, nucleophilicity, and leaving group quality to explain.
**Explanation:**
This reaction involves the conversion of an alkyl bromide (\(\text{CH}_3\text{CH}_2\text{Br}\)) and potassium acetate (\(\text{CH}_3\text{COOK}\)) to form an ester (\(\text{CH}_3\text{COOCH}_2\text{CH}_3\)) and potassium bromide (\(\text{KBr}\)).
1. **Nucleophilicity:**
- In this context, sodium iodide plays a critical role by enhancing the nucleophilicity of the reaction. Iodide ions (\(I^-\)) are better nucleophiles compared to bromide ions (\(Br^-\)) due to their larger size and higher polarizability.
2. **Leaving Group Quality:**
- The iodide ion can replace the bromide ion in the reaction, forming an alkyl iodide intermediate. This is because iodide is a better leaving group, which allows the reaction to proceed faster.
3. **Mechanism:**
- The substitution mechanism likely follows a \(S_N2\) pathway, where the iodide ion first substitutes the bromide, enhancing the overall reactivity and allowing the acetate ion to perform nucleophilic attack more efficiently.
The addition of sodium iodide, therefore, facilitates a faster reaction by improving the quality of the leaving group and enhancing the nucleophilicity of the anion responsible for the reaction.
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