2. Product A shown below, might be prepared 2 ways via a Williamson Ether synthesis, using different starting materials. Show the 2 possible routes. Which route would be preferred to make compound A? Why? Explain your choice. Compound A
2. Product A shown below, might be prepared 2 ways via a Williamson Ether synthesis, using different starting materials. Show the 2 possible routes. Which route would be preferred to make compound A? Why? Explain your choice. Compound A
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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![**Question:**
2. Product A shown below, might be prepared 2 ways via a Williamson Ether synthesis, using different starting materials. Show the 2 possible routes. Which route would be preferred to make compound A? Why? Explain your choice.
**Diagram Explanation:**
The image includes a structural diagram of Compound A, which is an ether composed of an isopropyl group (a branching with two methyl groups attached to a central carbon) linked via an oxygen atom to a methyl group.
**Discussion:**
To prepare Compound A using Williamson Ether Synthesis, there are two possible approaches involving different alkyl halides and alkoxides:
1. **Route 1:**
- **Starting Materials:** Isopropyl alcohol to form isopropoxide ion and methyl iodide.
- **Reaction:** Isopropoxide ion acts as a nucleophile and displaces the iodide ion from methyl iodide via an S_N2 reaction, forming Compound A.
2. **Route 2:**
- **Starting Materials:** Methyl alcohol to form methoxide ion and isopropyl iodide.
- **Reaction:** Methoxide ion attacks the isopropyl iodide, displacing iodide ion via an S_N2 mechanism to form Compound A.
**Preferred Route:**
Route 1 is preferred because:
- S_N2 reactions are more favorable with less steric hindrance. Methyl iodide offers less steric hindrance compared to isopropyl iodide, making the reaction with isopropoxide ion more efficient and faster.
- The formation of isopropoxide from isopropyl alcohol is generally more accessible and results in a more reactive alkoxide for the desired synthesis.
By selecting Route 1, the reaction conditions are more favorable, resulting in a higher yield and more efficient synthesis of Compound A.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F1a3704a0-1253-40d6-a99c-b2668c4bc107%2F455fd93f-787b-4fa6-bd04-82c96084398b%2Fq4lpb45_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Question:**
2. Product A shown below, might be prepared 2 ways via a Williamson Ether synthesis, using different starting materials. Show the 2 possible routes. Which route would be preferred to make compound A? Why? Explain your choice.
**Diagram Explanation:**
The image includes a structural diagram of Compound A, which is an ether composed of an isopropyl group (a branching with two methyl groups attached to a central carbon) linked via an oxygen atom to a methyl group.
**Discussion:**
To prepare Compound A using Williamson Ether Synthesis, there are two possible approaches involving different alkyl halides and alkoxides:
1. **Route 1:**
- **Starting Materials:** Isopropyl alcohol to form isopropoxide ion and methyl iodide.
- **Reaction:** Isopropoxide ion acts as a nucleophile and displaces the iodide ion from methyl iodide via an S_N2 reaction, forming Compound A.
2. **Route 2:**
- **Starting Materials:** Methyl alcohol to form methoxide ion and isopropyl iodide.
- **Reaction:** Methoxide ion attacks the isopropyl iodide, displacing iodide ion via an S_N2 mechanism to form Compound A.
**Preferred Route:**
Route 1 is preferred because:
- S_N2 reactions are more favorable with less steric hindrance. Methyl iodide offers less steric hindrance compared to isopropyl iodide, making the reaction with isopropoxide ion more efficient and faster.
- The formation of isopropoxide from isopropyl alcohol is generally more accessible and results in a more reactive alkoxide for the desired synthesis.
By selecting Route 1, the reaction conditions are more favorable, resulting in a higher yield and more efficient synthesis of Compound A.
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