Orgo Reagents and Resulting Products

Hydrohalogenation

• Addition of H-X to an alkene

• Regioselectivity: Markonikov, Anti-Markonikov when Peroxide is added

• Mechanism: Proton transfer, nucleophilic attack (check for carbocation rearrangements)

Acid-catalyzed Hydration

• Addition of H and OH across a pi bond

• Regioselectivity: Markovnikov

• Mechanism: Proton transfer, Nucleophilic attack, and deprotination

• Reagent: Sulfuric acid is usually the acid catalyst

• OH is added to the more substituted carbon

Oxymercuration-Demercuration

• Addition of H and OH across a pi bond

• Regioselectivity: Markovnikov

• No rearrangements

• Reagent: Usually NaBH4

Hydroboration - Oxidation

• Addition of H and OH across a pi bond

• Regioselectivity: Anti-Markovnikov

• Stereospecificity: Syn addition

• Mechanism: The less substituted carbon attacks the boron, and the more substituted carbon develops a partial positive charge, which triggers a hydride shift

• Reagent: BH3 * THF

Catalytic Hydrogenation

• Addition of H2 across a C=C double bond

• Stereospecificity: Syn addition

• Requires a metal catalyst

• “Removes” the double bond

Halogenation

Halohydrins