Select an appropriate method for preparing 1-methylcyclohexene from 1-methylcyclohexanol. O 1) TsCl, pyridine; 2) NaOMe O 1) TsCl, pyridine; 2) t-BuOK 1) MeMgCI; 2) H₂O O 1) PCC; 2) MeMgCl; 3) H₂O
Select an appropriate method for preparing 1-methylcyclohexene from 1-methylcyclohexanol. O 1) TsCl, pyridine; 2) NaOMe O 1) TsCl, pyridine; 2) t-BuOK 1) MeMgCI; 2) H₂O O 1) PCC; 2) MeMgCl; 3) H₂O
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
![**Select an appropriate method for preparing 1-methylcyclohexene from 1-methylcyclohexanol.**
- ○ 1) TsCl, pyridine ; 2) NaOMe
- ○ 1) TsCl, pyridine ; 2) t-BuOK
- ○ 1) MeMgCl ; 2) H₂O
- ○ 1) PCC ; 2) MeMgCl ; 3) H₂O
**Explanation of Options:**
1. **TsCl, pyridine ; NaOMe**: This pathway suggests using tosyl chloride with pyridine to convert the alcohol to a good leaving group, followed by sodium methoxide for elimination.
2. **TsCl, pyridine ; t-BuOK**: Similarly, this involves converting the alcohol to a tosylate and using potassium tert-butoxide, a strong base, for elimination.
3. **MeMgCl ; H₂O**: This involves the use of a Grignard reagent, which is not typically used for the conversion of alcohols to alkenes.
4. **PCC ; MeMgCl ; H₂O**: PCC oxidizes alcohols to carbonyls, which is not desired here. Additionally, MeMgCl with water suggests a Grignard reaction not relevant to alkene formation from alcohols.
**Note**: The goal is to perform a dehydration of the alcohol to yield the alkene, typically through an elimination reaction.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F28000c02-e2c6-4a8b-b2f9-904011bfd87b%2F8cb1ec4b-6eea-4b5e-885f-6c2ba9f4ed02%2F6dlm19_processed.png&w=3840&q=75)
Transcribed Image Text:**Select an appropriate method for preparing 1-methylcyclohexene from 1-methylcyclohexanol.**
- ○ 1) TsCl, pyridine ; 2) NaOMe
- ○ 1) TsCl, pyridine ; 2) t-BuOK
- ○ 1) MeMgCl ; 2) H₂O
- ○ 1) PCC ; 2) MeMgCl ; 3) H₂O
**Explanation of Options:**
1. **TsCl, pyridine ; NaOMe**: This pathway suggests using tosyl chloride with pyridine to convert the alcohol to a good leaving group, followed by sodium methoxide for elimination.
2. **TsCl, pyridine ; t-BuOK**: Similarly, this involves converting the alcohol to a tosylate and using potassium tert-butoxide, a strong base, for elimination.
3. **MeMgCl ; H₂O**: This involves the use of a Grignard reagent, which is not typically used for the conversion of alcohols to alkenes.
4. **PCC ; MeMgCl ; H₂O**: PCC oxidizes alcohols to carbonyls, which is not desired here. Additionally, MeMgCl with water suggests a Grignard reaction not relevant to alkene formation from alcohols.
**Note**: The goal is to perform a dehydration of the alcohol to yield the alkene, typically through an elimination reaction.
Expert Solution
![](/static/compass_v2/shared-icons/check-mark.png)
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
![Blurred answer](/static/compass_v2/solution-images/blurred-answer.jpg)
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](https://www.bartleby.com/isbn_cover_images/9781305957404/9781305957404_smallCoverImage.gif)
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
![Chemistry](https://www.bartleby.com/isbn_cover_images/9781259911156/9781259911156_smallCoverImage.gif)
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
![Principles of Instrumental Analysis](https://www.bartleby.com/isbn_cover_images/9781305577213/9781305577213_smallCoverImage.gif)
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
![Chemistry](https://www.bartleby.com/isbn_cover_images/9781305957404/9781305957404_smallCoverImage.gif)
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
![Chemistry](https://www.bartleby.com/isbn_cover_images/9781259911156/9781259911156_smallCoverImage.gif)
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
![Principles of Instrumental Analysis](https://www.bartleby.com/isbn_cover_images/9781305577213/9781305577213_smallCoverImage.gif)
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
![Organic Chemistry](https://www.bartleby.com/isbn_cover_images/9780078021558/9780078021558_smallCoverImage.gif)
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
![Chemistry: Principles and Reactions](https://www.bartleby.com/isbn_cover_images/9781305079373/9781305079373_smallCoverImage.gif)
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
![Elementary Principles of Chemical Processes, Bind…](https://www.bartleby.com/isbn_cover_images/9781118431221/9781118431221_smallCoverImage.gif)
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY