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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Question
Mechanism
Transcribed Image Text:**Title: Mechanism Steps of Ring-Opening Reaction**
**Description:**
**Objective:** Illustrate either the first three steps or the last three steps associated with the most likely mechanism of the ring-opening reaction.
**Reaction Overview:**
- **Reactants:**
- A cyclic ester (a lactone) with a carbonyl group (C=O) and an adjacent oxygen atom in the ring structure.
- Water (H₂O)
- **Catalyst:**
- Sulfuric acid (H₂SO₄)
**Mechanism Steps:**
1. **Initial Protonation:**
- The carbonyl oxygen undergoes protonation, facilitated by sulfuric acid, resulting in increased electrophilicity of the carbonyl carbon.
2. **Nucleophilic Attack:**
- Water acts as a nucleophile, attacking the electrophilic carbon of the carbonyl group, leading to the opening of the ring structure.
- A tetrahedral intermediate is formed as a consequence of the nucleophilic addition.
3. **Proton Transfer:**
- An internal proton transfer may occur, stabilizing the intermediates formed during the reaction and facilitating further transformations.
- This ensures the ring is open, and the molecule stabilizes as a linear structure.
**Note:** Each step involves careful changes in molecular structure and charge stabilization, leading towards the formation of a more stable ring-opened product.
This reaction is fundamental in organic chemistry, particularly in the study of ring-opening polymerizations and hydrolysis reactions. Understanding each step enriches comprehension of reaction mechanisms and the role of catalysts in organic transformations.
Expert Solution
Step 1: Reaction scheme
Given reaction scheme is shown below.
We have to give the mechanism of the reaction.
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