Consider the reaction between an alcohol and tosyl chloride, followed by a nucleophile. Write the condensed formula of the expected main organic product. 1. TSCI.pyridine CH,CH,OH 2. CI
Consider the reaction between an alcohol and tosyl chloride, followed by a nucleophile. Write the condensed formula of the expected main organic product. 1. TSCI.pyridine CH,CH,OH 2. 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...
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### Reaction of Alcohol with Tosyl Chloride and a Nucleophile
**Reaction Overview:**
The following chemical reaction involves an alcohol reacting with tosyl chloride (TsCl) in the presence of pyridine, followed by the addition of a nucleophile. The task is to determine the condensed formula of the expected main organic product.
**Chemical Reaction:**
- **Reactant:** Ethanol (\( \text{CH}_3\text{CH}_2\text{OH} \))
- **Reagents:**
1. Tosyl Chloride (TsCl), Pyridine
2. Chloride ion (\(\text{Cl}^-\))
**Explanation:**
1. **Step 1:** The hydroxyl group (\(-\text{OH}\)) in ethanol is converted to a tosylate group (\(-\text{OTs}\)) using tosyl chloride in the presence of pyridine. This reaction transforms the alcohol into a good leaving group.
2. **Step 2:** The tosylate group is then displaced by a nucleophile, in this case, the chloride ion (\(\text{Cl}^-\)), leading to the formation of chloroethane (\( \text{CH}_3\text{CH}_2\text{Cl} \)).
**Condensed Formula of the Expected Product:**
- Main Organic Product: **Chloroethane (\( \text{CH}_3\text{CH}_2\text{Cl} \))**
This reaction showcases a nucleophilic substitution mechanism where the hydroxyl group of an alcohol is replaced by a halogen via a tosylate intermediate.
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