O Macmillan Learning Consider the reaction between an alcohol and tosyl chloride, followed by a nucleophile. Write the condensed formula of the expected main organic product. CH₂CH₂CH₂OH 1. TsCl,pyridine 2. NC CH₂CH₂CN Incorrect 0
O Macmillan Learning Consider the reaction between an alcohol and tosyl chloride, followed by a nucleophile. Write the condensed formula of the expected main organic product. CH₂CH₂CH₂OH 1. TsCl,pyridine 2. NC CH₂CH₂CN Incorrect 0
Chemistry
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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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![**Title: Understanding the Reaction between Alcohol and Tosyl Chloride with a Nucleophile**
**Objective:**
Learn how to predict the main organic product formed in a reaction between an alcohol and tosyl chloride, followed by the introduction of a nucleophile.
**Body:**
**Reaction Description:**
The starting material for this reaction is an alcohol, specifically, propanol represented by the formula:
\[ \text{CH}_3\text{CH}_2\text{CH}_2\text{OH} \]
**Reaction Steps:**
1. **First Step: Reaction with Tosyl Chloride (TsCl) and Pyridine**
- The alcohol reacts with tosyl chloride in the presence of pyridine.
- This step transforms the alcohol into a tosylate, which is a better leaving group.
2. **Second Step: Nucleophilic Substitution**
- The tosylate product is then exposed to a nucleophile, specifically the cyanide ion (NC^-).
- This step results in nucleophilic substitution, replacing the tosylate group with the nucleophile to produce a nitrile.
**Expected Product:**
The expected product after these reactions should be butyronitrile, represented by the formula:
\[ \text{CH}_3\text{CH}_2\text{CH}_2\text{CN} \]
**Error Noted:**
In the transcription, an incorrect product was suggested:
\[ \text{CH}_3\text{CH}_2\text{CN} \]
This product is missing a methylene group (CH2), and hence it does not align with the starting material propanol.
**Conclusion:**
Understanding the mechanism of this reaction helps in predicting the correct structures of organic compounds formed through sequential reactions involving activation of alcohols and subsequent nucleophilic substitution.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F0f616c12-454b-42bc-a937-832375e70195%2F17a5f544-046a-47a2-8dd8-e2449ba2025f%2F2b7yuig_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Title: Understanding the Reaction between Alcohol and Tosyl Chloride with a Nucleophile**
**Objective:**
Learn how to predict the main organic product formed in a reaction between an alcohol and tosyl chloride, followed by the introduction of a nucleophile.
**Body:**
**Reaction Description:**
The starting material for this reaction is an alcohol, specifically, propanol represented by the formula:
\[ \text{CH}_3\text{CH}_2\text{CH}_2\text{OH} \]
**Reaction Steps:**
1. **First Step: Reaction with Tosyl Chloride (TsCl) and Pyridine**
- The alcohol reacts with tosyl chloride in the presence of pyridine.
- This step transforms the alcohol into a tosylate, which is a better leaving group.
2. **Second Step: Nucleophilic Substitution**
- The tosylate product is then exposed to a nucleophile, specifically the cyanide ion (NC^-).
- This step results in nucleophilic substitution, replacing the tosylate group with the nucleophile to produce a nitrile.
**Expected Product:**
The expected product after these reactions should be butyronitrile, represented by the formula:
\[ \text{CH}_3\text{CH}_2\text{CH}_2\text{CN} \]
**Error Noted:**
In the transcription, an incorrect product was suggested:
\[ \text{CH}_3\text{CH}_2\text{CN} \]
This product is missing a methylene group (CH2), and hence it does not align with the starting material propanol.
**Conclusion:**
Understanding the mechanism of this reaction helps in predicting the correct structures of organic compounds formed through sequential reactions involving activation of alcohols and subsequent nucleophilic substitution.
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