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...
Related questions
Question

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.
Expert Solution

This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
This is a popular solution!
Trending now
This is a popular solution!
Step by step
Solved in 2 steps with 2 images

Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Recommended textbooks for you

Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning

Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education

Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning

Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning

Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education

Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning

Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education

Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning

Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY