alkene addition reagents

HX

HYDROHALOGENATION

treatment with an alkene gives a Markovnikov addition of H and X across the alkene

HBr, ROOR

HYDROBROMINATION

treatment with an alkene gives an anti-Markovnikov addition of H and Br across the alkene

H3O+

ACID CATALYZED HYDRATION

treatment with an alkene gives a Markovnikov addition of H and OH across the alkene

1) Hg(OAC)2, H2O

2) NaBH4

OXYMERCURATION-DEMERCURATION

treatment with an alkene gives a Markovnikov addition of H and OH across the alkene, without any carbocation rearrangements

1) BH3 THF

2) H2O2, NaOH

HYDROBORATION-OXIDATION

treatment with an alkene gives an anti-Markovnikov addition of H and OH across the alkene; the reaction proceeds exclusively through syn addition

H2, Pt

HYDROGENATION

treatment with an alkene gives a syn addition of H and H across the alkene

Br2

BROMINATION

treatment with an alkene gives an anti addition of Br and Br across the alkene

Br2, H2O

HALOHYDRIN FORMATION

treatment with an alkene gives an anti addition of Br and OH across the alkene, with the OH group being installed at the more substituted position

1) RCO3H

2) H3O+

ANTI DIHYDROXYLATION

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

KMnO4, NaOH, cold

SYN DIHYDROXYLATION

treatment with an alkene gives a syn addition of OH and OH across the alkene

1) OsO4

2) NaHSO3, H2O

SYN DIHYDROXYLATION

treatment with an alkene gives a syn addition of OH and OH across the alkene

1) O3

2) DMS

OZONOLYSIS

causes cleavage of the C=C bond, giving two compounds, each of which possesses a C=O bond