Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Which of the following reagents can be used to convert 1-isopropylcyclopentene to 1-isopropylcyclopentanol?
Options
- AHBr
- BH ₂ / Pd
- CH ₂ O , dilute H ₂ SO ₄
- DH ₂ O , neutral
Correct answer
C. H ₂ O , dilute H ₂ SO ₄
Step-by-step solution
The conversion of 1-isopropylcyclopentene to 1-isopropylcyclopentanol involves the addition of water across the carbon-carbon double bond. This is an electrophilic addition reaction that follows Markovnikov's rule. The protonation of the double bond occurs to form the most stable carbocation, which in this case is a tertiary carbocation at the C1 position (bearing the isopropyl group). Water then attacks this tertiary carbocation to form 1-isopropylcyclopentanol. The reagent required for this acid-catalyzed hydrati