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...
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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.
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