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Show the detailed arrow pushing mechanism for the following amide hydrolysis. NH H,O* NH2 H2N H2N

Show the detailed arrow pushing mechanism for the following amide hydrolysis. NH H,O* NH2 H2N H2N

Chemistry
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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**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.
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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