Alkene Reactions

Hydroboration Reagents

1.) BH3 THF

2.) NaOH, H2O2 (OH replaces BH2)

Hydroboration regio and stereo

Anti-markivnikov, syn addition

Oxymercuration reagents

1.) Hg(OAC)2, H2O 2.) NaBH4 (H replaces Hg), NaOH, H2O

Oxymercuration regio/stereo

Markovnikov, syn and anti (rac)

Addition of HX reagents

HX (X=Cl, Br, etc)

Addition of HX regio/stereo

Markovnikov, syn and anti (rac)

Bromination (or Cl) regio/stereo

N/a, ANTI

Halohydrin formation reagents

X2, H2O

Halohydrin formation regio/stereo

Mark, anti (OH goes to most sub)

Dihydroxylation

OSO4

and H202, syn addition of OH

Ozonolysis reagents reductive

O3, -78, Me2S or NaHSO3

Ozonolysis Reagents oxidative

O3, -78, H2O2 (H becomes OH)

Hydrogenation

Syn addition of H

Epoxide opening

Anti addition, H3O+, H2O goes nto more substituted bond

Anti-Markovnikov Addition of H-Br reagents

HBr and ROOR

Radical addition of HBr

anti-mark, both syn and anti addition

Epoxidation (racemic) reagent

mCBPA (weak o—o bond)

Epoxidation (racemic) stereo

syn addition