H 2
Syn additionHCH 3
/Pt, Ni, or PdH
H H
HX (X = Cl, Br, I
or OSO 3 H)
Markovnikov addition
H CH 3H XHBr, ROOR
anti-Markovnikov addition
Br CH 3H HH 3 O+/H 2 O
Markovnikov addition
H CH 3H OHX CH 3H XX 2 /H 2 O
Anti addition, follows
X CH 3H OHMarkovnikov's ruleHydrogenationIonic Addition
of HXFree Radical
Addition of HBrHydrationHalohydrin
FormationCH 2 I 2 /Zn(Cu) (or
other conditions)
Syn additionHHCold dil. KMnO 4 or- OsO 4 , 2. NaHSO 3
HO OHHCH 3- KMnO 4 , OH−, heat
2. H 3 O+ CH 3
Carbene AdditionOxidative CleavageOzonlysisCH 2OOCH 3O
HCH 3X 2 (X = Cl, Br)
Anti addition HalogenationSyn addition Syn HydroxylationHO- O 3 , 2. Zn/HOAc
O