[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
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...
icon
Related questions
Question
Question 17
**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. - **
Expert Solution
steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Alcohols
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY