Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
1-Propanol can be prepared from propene using which of the following reagents?
Options
- AHg ( OAc )₂ / H ₂ O followed by NaBH ₄
- BH ₂ O / H ⁺
- CAll of these
- DB ₂ H ₆- THF followed by H ₂ O ₂ / OH ⁻
Correct answer
D. B ₂ H ₆- THF followed by H ₂ O ₂ / OH ⁻
Step-by-step solution
Propene is CH₃-CH=CH₂ . The preparation of 1-propanol ( CH₃-CH₂-CH₂-OH ) from propene requires the anti-Markovnikov addition of water across the double bond. Hydroboration-oxidation of alkenes results in the anti-Markovnikov addition of water. The reagents used for this process are B ₂ H ₆ in THF followed by oxidation with H ₂ O ₂ in an alkaline medium ( OH ⁻ ). Oxymercuration-demercuration ( Hg ( OAc )₂ / H ₂ O followed by NaBH ₄ ) and acid-catalyzed hydration ( H ₂ O / H ⁺ ) both follow Markovnikov's rule, which