2. The following alkene can be made using either of the two schemes below. Which pathway is better? PPH3 1. PPH3 Br H. 1. PPH3 Br 2. nBuLi PPH3 2. nBuLi
2. The following alkene can be made using either of the two schemes below. Which pathway is better? PPH3 1. PPH3 Br H. 1. PPH3 Br 2. nBuLi PPH3 2. nBuLi
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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Which is a better pathway?
![**Alkene Synthesis Pathways**
The following alkene can be synthesized using either of two pathways presented below. Consider the pathways and determine which is more efficient.
**Pathway Details:**
1. **First Pathway:**
- Starting material: Compound with bromine (Br) and a straight-chain alkyl group.
- Reagents:
- Step 1: Triphenylphosphine (PPh₃)
- Step 2: n-Butyllithium (n-BuLi)
The reaction involves forming a phosphonium salt using PPh₃, followed by deprotonation with n-BuLi, which prepares the ylide needed for the Wittig reaction.
2. **Second Pathway:**
- Starting material: Cyclopentanone
- Reagents:
- Triphenylphosphine (PPh₃)
- Step 1: Triphenylphosphine (PPh₃)
- Step 2: n-Butyllithium (n-BuLi)
Similar steps are involved as in the first pathway, with the substrate being a ketone instead of a bromoalkane.
**Diagram:**
The diagram provides a schematic for each pathway, showing the transformation of the starting materials into the same final alkene product. The intermediates and reaction conditions are indicated clearly, demonstrating the process of forming the double bond (alkene) through the Wittig reaction.
**Conclusion:**
Evaluate both pathways based on reaction conditions, efficiency, and yields to determine the optimal method for synthesizing the alkene.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fd35714a0-553b-4340-b19a-5fc4d72cbe54%2Faf19e467-d4e4-41f2-b037-29c7ec40d6d2%2Fhjq29a5_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Alkene Synthesis Pathways**
The following alkene can be synthesized using either of two pathways presented below. Consider the pathways and determine which is more efficient.
**Pathway Details:**
1. **First Pathway:**
- Starting material: Compound with bromine (Br) and a straight-chain alkyl group.
- Reagents:
- Step 1: Triphenylphosphine (PPh₃)
- Step 2: n-Butyllithium (n-BuLi)
The reaction involves forming a phosphonium salt using PPh₃, followed by deprotonation with n-BuLi, which prepares the ylide needed for the Wittig reaction.
2. **Second Pathway:**
- Starting material: Cyclopentanone
- Reagents:
- Triphenylphosphine (PPh₃)
- Step 1: Triphenylphosphine (PPh₃)
- Step 2: n-Butyllithium (n-BuLi)
Similar steps are involved as in the first pathway, with the substrate being a ketone instead of a bromoalkane.
**Diagram:**
The diagram provides a schematic for each pathway, showing the transformation of the starting materials into the same final alkene product. The intermediates and reaction conditions are indicated clearly, demonstrating the process of forming the double bond (alkene) through the Wittig reaction.
**Conclusion:**
Evaluate both pathways based on reaction conditions, efficiency, and yields to determine the optimal method for synthesizing the alkene.
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