Reagents for Addition Reactions

UVA Chem 2410 Frantz

HX

Halogenation: Markovnikov addition of H and X across the alkene

HBr, ROOR

Hydrobromination: anti-Markovnikov addition of H and Br across the alkene

H₃O+

Acid-Catalyzed Hydration: Markovnikov addition of H and OH across the alkene

1) Hg(OAc)₂, H₂O

2) NaBH₄

Oxymercuration-Demercuration: Markovnikov addition of H and OH across the alkene, without carbocation rearrangements

1) BH₃ * THF

2) H₂O₂, NaOH

Hydroboration-Oxidation: anti-Markovnikov addition of H and OH across the alkene. Rxn proceeds exclusively through syn addition

H₂, Pt

Hydrogenation: syn addition of H and H across the alkene

Br₂

Bromination: anti addition of Br and Br across the alkene

Br₂, H₂O

Halohydrin formation: anti addition of Br and OH across the alkene, with the OH group installed at the more substituted position

1) RCO₃H

2) H₃O+

Anti Dihydroxylation: treatment with peroxy acid (RCO3H) converts alkene into an epoxide, which is then opened upon treatment with aqueous acid to give a trans-diol

KMnO₄, NaOH, cold

Syn Dihydroxylation: syn addition of OH and OH across the alkene

1) OsO₄

2) NaHSO₃, H₂O

Syn Dihydroxylation: syn addition of OH and OH across the alkene

1) O₃

2) DMS

Ozonolysis: cleavage of C=C bond, giving two compounds, each of which possesses a C=O bond