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Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers

1-Methylcyclopentene can be converted into 2-methylcyclopentanol by:

Options

  1. Ahydroboration-oxidation
  2. Bepoxide formation followed by reduction with LiAlH ₄
  3. Coxymercuration-demercuration
  4. 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

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