H 2
Syn addition
HCH 3
/Pt, Ni, or Pd
H
H H
HX (X = Cl, Br, I
or OSO 3 H)
Markovnikov addition
H CH 3
H X
HBr, ROOR
anti-Markovnikov addition
Br CH 3
H H
H 3 O+/H 2 O
Markovnikov addition
H CH 3
H OH
X CH 3
H X
X 2 /H 2 O
Anti addition, follows
X CH 3
H OH
Markovnikov's rule
Hydrogenation
Ionic Addition
of HX
Free Radical
Addition of HBr
Hydration
Halohydrin
Formation
CH 2 I 2 /Zn(Cu) (or
other conditions)
Syn addition
HH
Cold dil. KMnO 4 or
- OsO 4 , 2. NaHSO 3
HO OH
HCH 3
- KMnO 4 , OH−, heat
2. H 3 O+ CH 3
Carbene Addition
Oxidative Cleavage
Ozonlysis
CH 2
OO
CH 3
O
H
CH 3
X 2 (X = Cl, Br)
Anti addition Halogenation
Syn addition Syn Hydroxylation
HO
- O 3 , 2. Zn/HOAc
O