12. Alcohols, Ethers, Epoxides and Thiols
Leaving Group Conversions Summary
12. Alcohols, Ethers, Epoxides and Thiols Leaving Group Conversions Summary
11PRACTICE PROBLEM
When cis- and trans-2-methylcyclopentanol undergo dehydration in warm sulfuric acid, the major alkene product formed is 1-methylcyclopent-1-ene. When the conversion to alkene is done via tosylation using TsCl and pyridine, followed by elimination using NaOCH3 (strong base), the two alcohols give different alkene products. The tosylate of cis-2-methylcyclopentanol forms mostly 1-methylcyclopent-1-ene, while trans-2-methylcyclopentanol only forms 3-methylcyclopent-1-ene. Explain how the regiochemical difference in the products is controlled by a stereochemical difference in the reactants.
When cis- and trans-2-methylcyclopentanol undergo dehydration in warm sulfuric acid, the major alkene product formed is 1-methylcyclopent-1-ene. When the conversion to alkene is done via tosylation using TsCl and pyridine, followed by elimination using NaOCH3 (strong base), the two alcohols give different alkene products. The tosylate of cis-2-methylcyclopentanol forms mostly 1-methylcyclopent-1-ene, while trans-2-methylcyclopentanol only forms 3-methylcyclopent-1-ene. Explain how the regiochemical difference in the products is controlled by a stereochemical difference in the reactants.