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: Detailed Mechanism of Amide Hydrolysis**
**Introduction:**
This educational resource explains the arrow-pushing mechanism for the hydrolysis of an amide, illustrating the transformation of a sulfonamide compound under acidic conditions and heat.
**Reaction Overview:**
The given reaction shows a sulfonamide compound as a substrate, which undergoes hydrolysis in the presence of hydronium ions (\( \text{H}_3\text{O}^+ \)) and heat (\( \Delta \)) to form an aromatic amine.
**Reactants and Product:**
- **Reactant:**
- An aromatic sulfonamide with the structure:
- A benzene ring attached to a sulfonamide group (\( \text{SO}_2\text{NH} \)) and an acetamide group (\( \text{NHCOCH}_3 \)).
- **Product:**
- An aromatic amine where the acetamide group is replaced with an amine group (\( \text{NH}_2 \)).
**Mechanism:**
1. **Protonation:**
- The carbonyl oxygen of the acetamide group is protonated by hydronium ions, increasing the electrophilicity of the carbonyl carbon.
2. **Nucleophilic Attack:**
- Water acts as a nucleophile and attacks the carbonyl carbon, leading to the formation of a tetrahedral intermediate.
3. **Deprotonation & Collapse:**
- The tetrahedral intermediate collapses, expelling the amine, and forming a carboxylic acid intermediate.
4. **Final Product Formation:**
- The carboxylic acid intermediate is deprotonated to stabilize the product, resulting in the aromatic amine.
**Conclusion:**
This mechanism exemplifies typical steps involved in acid-catalyzed amide hydrolysis, including protonation, nucleophilic attack, and expulsion of a leaving group. Understanding these steps aids in grasping the fundamental concept of hydrolysis reactions in organic chemistry.
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