
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Transcribed Image Text:### Acid-Catalyzed Epoxide Ring-Opening Reaction
**Reaction Overview:**
The product of the acid-catalyzed epoxide ring-opening reaction shown below is formed as a racemic mixture.
**Chemical Reaction:**
- Structure: An epoxide ring (cyclic ether) is treated with \( \text{H}_3\text{O}^+ \).
- Result: The ring opens.
**Mechanism Step:**
- Task: Draw curved arrows to illustrate electron reorganization. Focus on forming one of the product stereoisomers.
**Diagrams:**
1. **Initial Structure:**
- A three-membered cyclic ether structure (epoxide) with two carbon atoms connected by an oxygen atom.
- Attached are hydrogens and an additional \( \text{H}_3\text{O}^+ \) indicating acidic conditions.
2. **Mechanism:**
- Arrow-pushing is required to show how electrons move during the reaction.
- The product demonstrates one potential stereoisomer formation.
**Arrow-Pushing Instructions:**
- Use curved arrows to demonstrate electron pair movements.
- Start arrows from electron-rich areas (lone pairs or bonds) to electron-deficient areas.
**Note:**
Students should consider factors like stereochemistry while drawing mechanisms to understand product formation and potential stereoisomers thoroughly.
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