Which compound is the dominant product of the reaction below? (1) LIAID /ether (2) dil. H*H,0 OH HOH "D HO, Compound A Compound B Compound C Compound D
Which compound is the dominant product of the reaction below? (1) LIAID /ether (2) dil. H*H,0 OH HOH "D HO, Compound A Compound B Compound C Compound D
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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![**Reaction Analysis for Dominant Product Identification**
**Question:**
Which compound is the dominant product of the reaction below?
**Reaction Details:**
- Starting compound: A cyclic epoxide
- Reagents and conditions:
1. Lithium aluminum deuteride (LiAlD₄) in ether
2. Dilute acid (H⁺/H₂O)
**Possible Products:**
- **Compound A:** Cyclohexanol with an OH group and a deuterium (D) atom on adjacent carbons.
- **Compound B:** Cyclohexanol with an OH group and a deuterium (D) atom on adjacent carbons, with both substituents on the same side.
- **Compound C:** Cyclohexanol with a deuterium (D) atom and an OH group on opposite sides, positioned on non-adjacent carbons.
- **Compound D:** Cyclohexanol with an OH group and a deuterium (D) atom on opposite sides, positioned on adjacent carbons.
**Answer Choices:**
- ○ Compound A
- ○ Compound D
- ○ Compound C
- ○ Compound B
---
**Explanation:**
The reaction involves the reduction of an epoxide with LiAlD₄, which selectively delivers deuterium to one carbon of the epoxide ring. Following hydronium workup leads to hydroxylation at the other carbon. Understanding the stereochemistry and regiochemistry is essential for predicting the dominant product.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fc0f85ff8-2ea0-4d43-a0c0-84de96cc63b8%2F9e8d94ce-d444-423f-98a8-36ac5b1efe2a%2Fx2k3t5a_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Reaction Analysis for Dominant Product Identification**
**Question:**
Which compound is the dominant product of the reaction below?
**Reaction Details:**
- Starting compound: A cyclic epoxide
- Reagents and conditions:
1. Lithium aluminum deuteride (LiAlD₄) in ether
2. Dilute acid (H⁺/H₂O)
**Possible Products:**
- **Compound A:** Cyclohexanol with an OH group and a deuterium (D) atom on adjacent carbons.
- **Compound B:** Cyclohexanol with an OH group and a deuterium (D) atom on adjacent carbons, with both substituents on the same side.
- **Compound C:** Cyclohexanol with a deuterium (D) atom and an OH group on opposite sides, positioned on non-adjacent carbons.
- **Compound D:** Cyclohexanol with an OH group and a deuterium (D) atom on opposite sides, positioned on adjacent carbons.
**Answer Choices:**
- ○ Compound A
- ○ Compound D
- ○ Compound C
- ○ Compound B
---
**Explanation:**
The reaction involves the reduction of an epoxide with LiAlD₄, which selectively delivers deuterium to one carbon of the epoxide ring. Following hydronium workup leads to hydroxylation at the other carbon. Understanding the stereochemistry and regiochemistry is essential for predicting the dominant product.
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