For each of the following reactions, provide a complete, detailed mechanism and predict the major product(s), including stereochemistry where appropriate. Br NaCN CH2Cl2 OH 20 Heat
For each of the following reactions, provide a complete, detailed mechanism and predict the major product(s), including stereochemistry where appropriate. Br NaCN CH2Cl2 OH 20 Heat
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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Transcribed Image Text:### Reaction Mechanisms and Predicting Major Products
#### Question:
For each of the following reactions, provide a complete, detailed mechanism and predict the major product(s), including stereochemistry where appropriate.
#### Reaction 1:
**Reactant:**
- A cyclohexyl bromide compound where the bromine is attached to a secondary carbon.
**Reagents:**
- Sodium cyanide (NaCN)
- Solvent: Dichloromethane (CH₂Cl₂)
**Diagram Explanation:**
- The bromine (Br) is on a cyclohexane ring.
**Expected Reaction:**
- Sodium cyanide will facilitate a nucleophilic substitution reaction, potentially leading to the substitution of the bromine with a cyano group (CN).
---
#### Reaction 2:
**Reactant:**
- A bicyclic compound with a hydroxyl group (OH) attached to a secondary carbon.
**Reagents:**
- Acid (H⁺) and water (H₂O)
- Heat
**Diagram Explanation:**
- The compound consists of a fused bicyclic ring system with a hydroxyl group substituent.
**Expected Reaction:**
- The presence of an acid and heat suggests a dehydration reaction, possibly forming an alkene as the major product.
### Detailed Mechanism and Stereochemistry:
- For each reaction, consider the mechanism involved (e.g., SN2 for substitution, E1/E2 for elimination).
- Analyze the stereochemistry based on the starting material and product stability.
#### Summary:
These reactions illustrate different types of organic transformations involving substitution and elimination, where conditions and reagents significantly influence the product outcome. Understanding the mechanistic steps and the influence of stereochemistry is crucial for predicting major products in organic synthesis.
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