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Multiple Choice
Which of the following reactions is used to convert an alkene into an alcohol?
A
Friedel-Crafts alkylation
B
Halogenation
C
Dehydration
D
Hydroboration-oxidation
Verified step by step guidance
1
Identify the functional group transformation: The problem asks for a reaction that converts an alkene into an alcohol. This involves adding an -OH group to the alkene.
Understand the mechanism of hydroboration-oxidation: This reaction involves two main steps. First, the alkene undergoes hydroboration, where borane (BH3) adds across the double bond. Second, oxidation occurs, typically using hydrogen peroxide (H2O2) in the presence of a base, converting the boron-attached intermediate into an alcohol.
Recognize the regioselectivity: Hydroboration-oxidation is known for its anti-Markovnikov addition, meaning the -OH group is added to the less substituted carbon of the alkene.
Consider the stereochemistry: This reaction proceeds with syn addition, where both the hydrogen and the hydroxyl group add to the same side of the alkene, resulting in a specific stereochemical outcome.
Compare with other reactions: Friedel-Crafts alkylation involves adding an alkyl group to an aromatic ring, halogenation adds halogens to alkenes, and dehydration typically removes water from alcohols to form alkenes. None of these reactions convert alkenes to alcohols.