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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Need help with Part 3
![## Dehydration of Alcohol and Formation of Isomeric Alkenes
### Overview
When alcohol \( V \) is treated with \( \text{POCl}_3 \) and pyridine, it forms a single alkene \( W \). However, upon dehydration with \( \text{H}_2\text{SO}_4 \), three isomeric alkenes \( X \), \( Y \), and \( Z \) are produced.
### Chemical Reaction
- **Starting Material:** Alcohol \( V \)
- **Reagents:** \( \text{POCl}_3 \), pyridine, \( \text{H}_2\text{SO}_4 \)
- **Products:** Alkenes \( W \), \( X \), \( Y \), \( Z \)
\[ \text{Alcohol V} \xrightarrow{\text{POCl}_3/\text{pyridine}} \text{Alkene W} \]
\[ \text{Alkene W} \xrightarrow{\text{H}_2\text{SO}_4} \text{Alkenes X, Y, Z} \]
---
### Part 1: Identification of the Correct Starting Mechanism
**Choose the Correct Starting Mechanism:**
Each of these three mechanisms involves the same starting material \( V \) and proceeds with different steps involving the formation of a secondary carbocation.
1. **Mechanism 1**:
\[
\text{OH Group Protonation} \rightarrow \text{Carbocation Formation} \rightarrow \text{Water Elimination}
\]
2. **Mechanism 2**:
- Similar protonation and elimination steps discussed for mechanism 1.
3. **Mechanism 3**:
- Similar protonation and elimination steps.
(Correct mechanism highlighted with a check mark.)
---
### Part 2: Intermediate Formation
**Task:** Draw the intermediate formed upon rearrangement of the secondary carbocation generated in Part 1.
- **Intermediate Structure Diagram:**
(Click "view structure" for a detailed molecular configuration)
---
### Part 3: Correlation of Mechanisms to Products
**Select Which Mechanism (I, II, or III) Leads to Each Product:**
1. **Mechanism I:**
- Leads to a 3° carbocation through rearrangement.
2. **](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fe8ef1885-1d5b-4182-acd8-ef29b30bccf5%2F136a1f6b-eb0e-42a7-89f6-9c3574e7c516%2Fkhk9889_processed.jpeg&w=3840&q=75)
Transcribed Image Text:## Dehydration of Alcohol and Formation of Isomeric Alkenes
### Overview
When alcohol \( V \) is treated with \( \text{POCl}_3 \) and pyridine, it forms a single alkene \( W \). However, upon dehydration with \( \text{H}_2\text{SO}_4 \), three isomeric alkenes \( X \), \( Y \), and \( Z \) are produced.
### Chemical Reaction
- **Starting Material:** Alcohol \( V \)
- **Reagents:** \( \text{POCl}_3 \), pyridine, \( \text{H}_2\text{SO}_4 \)
- **Products:** Alkenes \( W \), \( X \), \( Y \), \( Z \)
\[ \text{Alcohol V} \xrightarrow{\text{POCl}_3/\text{pyridine}} \text{Alkene W} \]
\[ \text{Alkene W} \xrightarrow{\text{H}_2\text{SO}_4} \text{Alkenes X, Y, Z} \]
---
### Part 1: Identification of the Correct Starting Mechanism
**Choose the Correct Starting Mechanism:**
Each of these three mechanisms involves the same starting material \( V \) and proceeds with different steps involving the formation of a secondary carbocation.
1. **Mechanism 1**:
\[
\text{OH Group Protonation} \rightarrow \text{Carbocation Formation} \rightarrow \text{Water Elimination}
\]
2. **Mechanism 2**:
- Similar protonation and elimination steps discussed for mechanism 1.
3. **Mechanism 3**:
- Similar protonation and elimination steps.
(Correct mechanism highlighted with a check mark.)
---
### Part 2: Intermediate Formation
**Task:** Draw the intermediate formed upon rearrangement of the secondary carbocation generated in Part 1.
- **Intermediate Structure Diagram:**
(Click "view structure" for a detailed molecular configuration)
---
### Part 3: Correlation of Mechanisms to Products
**Select Which Mechanism (I, II, or III) Leads to Each Product:**
1. **Mechanism I:**
- Leads to a 3° carbocation through rearrangement.
2. **
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