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

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**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.
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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