Alkenes CH3
H
H3C
CH3
CH3 OH
H
H3C
OH
CH3 OH
CH3 H3C
H OH Anti markovnokov CH3 H3C
OsO4/H2O2 Or KMnO4/OH-
CH3 H
H
anti addition H
CH3
X2/H2O
BH3/THF H2O2/OH-
Syn addition
H
X
Syn addition
H
CH3
H3C
H2/Pt
CH3 H markovnokov
OH
anti addition
1)Hg(OAc)2/H2O 2)NaBH4/OH-
CH3 X
H3C
H3C
CH3 X
CH3
X2/CCl4
H
H3C
anti addition H3C
CH3
markovnokov
H
O Ph
CH3
HX H3C
CH3 X
HX/R-O-O-R Anti markovnokov
OOH
CH3 X H 3C
O
H
KMnO4,warm, conc
O3/(CH3)2S
H3C
CH3
Or
H
O3 /Zn/HCl
H3C
CH3 O
+ O H
H3C
CH3
H3C O+ O H3C CH3
O OH
1
H
H
H
H
Alkynes
H3C
H
H
H
H
H
H
H
H
M/NH3 M=Li, Na orK
H H
Syn addition
Syn addition of H2
H2/Pd/BaSO4 quinoline Or Lindlar Catalyst
H O Anti markovnokov
X H
X
H3C
H
X2/CCl4
NaNH2/NH3
HX
H3C
X
H
X
H
H3C
H
H
H X H3C
Anti markovnokov C- Na+
O3/(CH3)2S
Or KMnO4,warm, conc/OH-
CH3CH2X
R -OH X/R-O H
H3C
X
H
SN2, works just with a primary
H3C
H
HX/R-O-O-R
H X
H3C
2 NaNH2/H2O 150oC
X
H3C X
HX
H
markovnokov
markovnokovX
anti addition
X
H O
HgSO4/H2SO4 H2O
1 mole X2/CCl4
H
BH3/THF H2O2/OH- H C 3
H2/Pt H3C
H
H3C
anti addition of H2
H H H3C
H3C
OH
HO O+ O
H
H3C
2
H H X
Reaction of Aromatic compounds Br NO2
H2/Ru 100oC, 1000 psi Br2/FeBr3
HNO3/H2SO4
O
SO3H R
O
R Cl
Ketone Friedel-Craft acylation
SO3/H2SO4 H2O, heat
, AlCl3
(CH3)3C-Cl AlCl3 Or (CH3)3C-OH H2SO4 Or (CH3)2C=CH2 HF
CO/HCl AlCl3/CuCl
O
C(CH3)3
H Friedel-Craft alkylation Benzaldehyde Gatterman-Koch formylation
Substituant affects • Alkyls, -NH2, -NH-CO(R), -OR , -OH, -O- are electron donating groups are avtivators, ortho and para directors. • Cl, Br, F, I, electron withdrawing group are deactivators but ortho and para directors. • -NO2, -SO3H, -N+R3, acyl, -CN withdrawing group are deactivators, meta directors
3
ED ED
M/NH3 , ROH M=Li, Na or K
EW
EW
Birch Reduction
Side chain reactions O
Clemmensen reduction
Zn/Hg HCl
O
Br OH
KMnO4 conc,hot H2O
Br2/hν
oxydation (CH3)3CO-,Na+
excess Cl2/hν
H2/Pd
SN2 Nuor SN1 Nu
Cl Cl Cl Cl
+ Br-
Cl
4
