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[References] Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. O OH + H₂N CI

[References] Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. O OH + H₂N CI

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: Understanding Tetrahedral Intermediates in Acyl Transfer Reactions** In acyl transfer reactions (nucleophilic substitution at carbonyl), the reaction proceeds in two stages via a "tetrahedral intermediate." Here, we'll explore the formation of this intermediate through a given reaction. **Reaction Overview:** The reaction involves a compound with the structure: - A benzene ring attached to a carbonyl group (C=O) with a chlorine (Cl) substituent on the carbonyl carbon. - This is reacted with a molecule containing an amine group (NH2) and a hydroxyl group (OH). **Steps to Draw the Tetrahedral Intermediate:** 1. **Identify the Reactants:** - Reactant 1: A benzene ring attached to a carbonyl group (C=O) with a chlorine (Cl) substituent on the carbonyl carbon. - Reactant 2: Molecule with an amine group (NH2) and a hydroxyl group (OH). 2. **Formation of the Intermediate:** - The nucleophilic attack takes place when the amine nitrogen (NH2) attacks the carbonyl carbon (C=O) of the benzoyl chloride. 3. **After the Nucleophilic Attack:** - This attack results in the addition of the nucleophile (NH2 group) to the carbonyl carbon, breaking the double bond (C=O) and forming a single bond (C-OH). The carbon now has four single bonds, making it a tetrahedral intermediate. **Key Points:** - You do not have to consider stereochemistry. - Include all valence lone pairs in your drawing. - Do not include counter-ions like \( \text{Na}^+ \) or \( \text{I}^- \). - If more than one intermediate can be formed, just draw one. **Diagrams:** The diagram editor tools available will allow you to draw the various bonds and lone pairs needed to represent the tetrahedral intermediate accurately. - **Benzene ring structure**: Use the hexagon symbol. - **Carbonyl group (C=O)**: Draw the double bond from the hexagon (benzene) to the oxygen atom. - **Chlorine substituent**: Draw the Cl atom on the carbonyl carbon before reaction and indicate its replacement after the nucleophilic attack. - **
Transcribed Image Text:**Title: Understanding Tetrahedral Intermediates in Acyl Transfer Reactions** In acyl transfer reactions (nucleophilic substitution at carbonyl), the reaction proceeds in two stages via a "tetrahedral intermediate." Here, we'll explore the formation of this intermediate through a given reaction. **Reaction Overview:** The reaction involves a compound with the structure: - A benzene ring attached to a carbonyl group (C=O) with a chlorine (Cl) substituent on the carbonyl carbon. - This is reacted with a molecule containing an amine group (NH2) and a hydroxyl group (OH). **Steps to Draw the Tetrahedral Intermediate:** 1. **Identify the Reactants:** - Reactant 1: A benzene ring attached to a carbonyl group (C=O) with a chlorine (Cl) substituent on the carbonyl carbon. - Reactant 2: Molecule with an amine group (NH2) and a hydroxyl group (OH). 2. **Formation of the Intermediate:** - The nucleophilic attack takes place when the amine nitrogen (NH2) attacks the carbonyl carbon (C=O) of the benzoyl chloride. 3. **After the Nucleophilic Attack:** - This attack results in the addition of the nucleophile (NH2 group) to the carbonyl carbon, breaking the double bond (C=O) and forming a single bond (C-OH). The carbon now has four single bonds, making it a tetrahedral intermediate. **Key Points:** - You do not have to consider stereochemistry. - Include all valence lone pairs in your drawing. - Do not include counter-ions like \( \text{Na}^+ \) or \( \text{I}^- \). - If more than one intermediate can be formed, just draw one. **Diagrams:** The diagram editor tools available will allow you to draw the various bonds and lone pairs needed to represent the tetrahedral intermediate accurately. - **Benzene ring structure**: Use the hexagon symbol. - **Carbonyl group (C=O)**: Draw the double bond from the hexagon (benzene) to the oxygen atom. - **Chlorine substituent**: Draw the Cl atom on the carbonyl carbon before reaction and indicate its replacement after the nucleophilic attack. - **
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