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Reaction List - Ch 12Reactions of Alkenes (II)
Addition of X2
Addition of X2 with H2O
Catalytic Hydrogenation
Hydroxylation
H2
Pd/C
H adds to both sides of C=Cexcess hydrogen is always presentsyn addition
alkane
KMnO4
H2O, NaOHOH
OH
OH is added to both sides of C=Csyn addition
OsO4
H2O2
or
halogen is added to both sides of C=C
Cl2 or Br2 may be used (diiodides are not very stable)
anti addition
Br2Br
Br
vicinal diol
vicinal dihalide
OH is added to more substituted side, halogen to less
Cl2, Br2, or I2 may be used
anti addition
Br2 OH
Br
H2O
halohydrin
Cyclopropanation
Polymerization
Oxidative cleavage:
Epoxidation
O
OPhOH
+O
reagent may be abbreviated PhCO3H
syn addition
CH2N2
heat or light
orCH2I2
Zn, CuCl
CHBr3
(CH3)3COK
Br
Br
carbene is formed in each casesyn addition
orH2SO4 ROOR
heat or light
acid creates carbocation; peroxide creates radicalcarbocation or radical react with another alkene
O3
O3
(CH3)2S
H2O2
O
O
HH
O
O
OHH
epoxide
cyclopropane
polymer
aldehydes and/or ketones
carboxylic acids and/or ketones
cyclic compounds give dicarbonyl compoundsif the C=C is symmetrical, only one product is formed