Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
1-Methylcyclopentene can be converted into 2-methylcyclopentanol by:
Options
- Ahydroboration-oxidation
- Bepoxide formation followed by reduction with LiAlH ₄
- Coxymercuration-demercuration
- Dacid-catalyzed hydration
Correct answer
A. hydroboration-oxidation
Step-by-step solution
1-Methylcyclopentene contains a double bond between a tertiary carbon (C1, bearing the methyl group) and a secondary carbon (C2). To convert 1-methylcyclopentene into 2-methylcyclopentanol, the hydroxyl group ( -OH ) must be added to the less substituted carbon (C2) and the hydrogen atom to the more substituted carbon (C1). This corresponds to the anti-Markovnikov addition of water across the double bond. Hydroboration-oxidation of alkenes proceeds via anti-Markovnikov addition, yielding 2-methylcyclopentanol. Oxym