Provide the correct order for the mechanistic steps for the following reaction: OH Br HBr H20 racemic Step 1 v [ Choose ] Carbocation formation Nucleophilic attack Step 2 Leaving group leaves Proton transfer Step 3 [ Choose ] Step 4 [Choose ]
Provide the correct order for the mechanistic steps for the following reaction: OH Br HBr H20 racemic Step 1 v [ Choose ] Carbocation formation Nucleophilic attack Step 2 Leaving group leaves Proton transfer Step 3 [ Choose ] Step 4 [Choose ]
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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![### Mechanistic Steps in Organic Reactions: HBr Addition to Alcohol
**Objective:**
Provide the correct order for the mechanistic steps for the following reaction:
**Reaction:**
\[ \text{CH}_3\text{CH(OH)-CH}_3 + \text{HBr} \rightarrow \text{CH}_3\text{CH(Br)-CH}_3 + \text{H}_2\text{O} \]
This reaction results in a racemic mixture where an alcohol group (-OH) is converted into a bromide (-Br) through the addition of hydrobromic acid (HBr).
**Steps to Determine:**
1. **Step 1: [Choose]**
2. **Step 2: [Choose]**
3. **Step 3: [Choose]**
4. **Step 4: [Choose]**
**Options:**
- **Carbocation formation**
- **Nucleophilic attack**
- **Leaving group leaves**
- **Proton transfer**
---
**Detailed Explanation of the Steps Involved:**
1. **Proton Transfer:**
The reaction begins with the proton transfer where the hydroxyl group of the alcohol is protonated by HBr, resulting in the formation of a good leaving group (water).
2. **Leaving Group Leaves:**
After protonation, the water molecule, now a good leaving group, leaves, leading to the formation of a carbocation intermediate.
3. **Carbocation Formation:**
The departure of water leads to the formation of a carbocation intermediate. This step is crucial as it dictates the subsequent steps of the mechanism.
4. **Nucleophilic Attack:**
Finally, the bromide ion (Br-) from hydrobromic acid attacks the positively charged carbocation, resulting in the formation of the final product, a racemic mixture of bromide-substituted compound.
**Interactive Section:**
Please select the correct order of the mechanistic steps from the dropdowns provided.
- **Step 1:**
- [Choose: Proton transfer]
- **Step 2:**
- [Choose: Leaving group leaves]
- **Step 3:**
- [Choose: Carbocation formation]
- **Step 4:**
- [Choose: Nucleophilic attack]
This section will help you solidify your understanding of the mechanistic steps involved in the reaction. Understanding these steps](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fb7a6ddd6-9522-4c7e-bff1-23d6943042e2%2F0c0897d6-ffab-4a78-895d-364808ade892%2F0jgsetk_processed.jpeg&w=3840&q=75)
Transcribed Image Text:### Mechanistic Steps in Organic Reactions: HBr Addition to Alcohol
**Objective:**
Provide the correct order for the mechanistic steps for the following reaction:
**Reaction:**
\[ \text{CH}_3\text{CH(OH)-CH}_3 + \text{HBr} \rightarrow \text{CH}_3\text{CH(Br)-CH}_3 + \text{H}_2\text{O} \]
This reaction results in a racemic mixture where an alcohol group (-OH) is converted into a bromide (-Br) through the addition of hydrobromic acid (HBr).
**Steps to Determine:**
1. **Step 1: [Choose]**
2. **Step 2: [Choose]**
3. **Step 3: [Choose]**
4. **Step 4: [Choose]**
**Options:**
- **Carbocation formation**
- **Nucleophilic attack**
- **Leaving group leaves**
- **Proton transfer**
---
**Detailed Explanation of the Steps Involved:**
1. **Proton Transfer:**
The reaction begins with the proton transfer where the hydroxyl group of the alcohol is protonated by HBr, resulting in the formation of a good leaving group (water).
2. **Leaving Group Leaves:**
After protonation, the water molecule, now a good leaving group, leaves, leading to the formation of a carbocation intermediate.
3. **Carbocation Formation:**
The departure of water leads to the formation of a carbocation intermediate. This step is crucial as it dictates the subsequent steps of the mechanism.
4. **Nucleophilic Attack:**
Finally, the bromide ion (Br-) from hydrobromic acid attacks the positively charged carbocation, resulting in the formation of the final product, a racemic mixture of bromide-substituted compound.
**Interactive Section:**
Please select the correct order of the mechanistic steps from the dropdowns provided.
- **Step 1:**
- [Choose: Proton transfer]
- **Step 2:**
- [Choose: Leaving group leaves]
- **Step 3:**
- [Choose: Carbocation formation]
- **Step 4:**
- [Choose: Nucleophilic attack]
This section will help you solidify your understanding of the mechanistic steps involved in the reaction. Understanding these steps
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