Alkene Addition Diagrams
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22 Terms
1. BH3
2. H2O2, OH-
Hydroboration
1. Hg(OAc)2 , H2O
2. NaBH4
(OAc = O2CCH3)
Oxymercuration-Demurcuration
1. Hg(OAc)2 , ROH
2. NaBH4
(OAc = O2CCH3)
Alkoxymercuration-Demurcuration
H3O+
Acid-Catalyzed Hydration
ROH, H+
or
ROH, H3PO4
or
ROH, H2SO4
Acid-catalyzed addition of an alcohol
HCl
Hydrohalogenation
HBr
Hydrohalogenation
HI
Hydrohalogenation
HBr, ROOR
Radical Addition of HBr
Br2 / CCl4
Halogenation (bromination)
Cl2 / CCl4
Halogenation (chlorination)
Br2 , H2O
Halohydrin Formation
Cl2 , H2O
Halohydrin Formation
1. mCPBA
2. H3O+
or
1. RCO3H
2. H3O+
Anti-Dihydroxylation
1. OsO4
2. H2O2
or
OsO4 , NMO
or
KMnO4 (dilute, cold)
Syn-Dihydroxylation
H2 , Pd/C
or
H2 , Pt or PtO2
or
H2 , Ni
Hydrogenation (Catalytic Reduction)
mCPBA
or
RCO3H
Epoxidation
1. O3
2. (CH3)2S
or
1. O3
2. Zn/H+
Reductive Ozonolysis
1. O3
2. H2O2
Oxidative Ozonolysis
KMnO4 (hot, conc)
Oxidative Cleavage
CH2I2 , Zn(Cu)
Cyclopropanation (Simmons–Smith Reaction)
CHCl3 , OH-
Cyclopropanation (Carbene Addition)
Note 
Flashcards (229)