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

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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.
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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