Reactions of Alkenes

1) H2, Pd/C or Pt

hydrogenation, forms alkane

syn addition

1) Hg(OAc)2, H2O or ROH

2) NaBH4

alkoxymercuration, forms OH

markovnikov

OH from H2O adds to area with less H

H adds to area with more H

1) BH3•THF 2) H2O2, OH–

hydroboration, forms OH

anti-mark

H adds to area with LESS H

OH adds to area with MORE H

syn-additon

1) X2, H2O (e.g., Br2, H2O)

halohydrin formation

anti-addition

Cl adds to more H side

OH adds to less H side

cuz OH>Cl

1) mCPBA (RCO3H)

epoxide formation

syn-additon

1) mcbpa/peroxyacid in water

anti-addition

forms two trans OH

epoxide opens in water

1) HX

alkyl halide

mark

Cl to less H side

H to more H side

1) HX, ROOR

alkyl halide

anti-mark

Cl to more H

H to less H

1) X2 (e.g., Br2 or Cl2), CCl4

anti-addition

forms dihalide

1) OsO4, H2O2 or KMnO4 (cold, dilute)

syn addition

OH’s on same side

1) O3

2) DMS or Zn/H2O

or

1) KMO4

ozonolysis, forms aldehyde and ketone

1) KMnO4

2) H3O+

forms a ketone and carboxylate/carbon dioxide (+water), ozonolysis

DMSO vs DMS

dimethyl sulfoxide

dimethyl sulfide

mCPBA

m-Chloroperoxybenzoic acid

1) H2O

2) H3O+/H+

hydration, forms OH

mark