Alkenes

CH3 H
CH3 H
H3C CH3 CH3 OH
H3C CH3
OH OH
H3C CH3
H OH
Anti markovnokov X H
CH3
Syn addition anti addition
H
OsO4/H2O2
H3C CH3 Or CH3 H
KMnO4/OH- X2/H2O
H H BH3/THF H3C CH3
Syn addition H2O2/OH-
H2/Pt OH H markovnokov
1)Hg(OAc)2/H2O anti addition
2)NaBH4/OH-
CH3 X H3C CH3
HX CH3
H3C CH3
X2/CCl4 H

markovnokov H3C CH3

X H
anti addition H3C H
X H
O HX/R-O-O-R
Ph OOH
H3C CH3 Anti markovnokov
CH3 X
H 3C O H H3C
KMnO4,warm, O3/(CH3)2S CH3
conc
Or H H
O3 /Zn/HCl

H3C CH3
O + O H3C CH3
H3C H O+ O
H3C H

CH3
O
OH

1
 Alkynes

H3C H
H
H3C H H H
H H3C
Syn addition of H2 H O
H H Anti markovnokov
anti addition of H2
H H
H3C H H2/Pd/BaSO4 H
M/NH3 BH3/THF
quinoline
H H M=Li, Na orK H2O2/OH- H C H
Or 3
Syn addition Lindlar Catalyst
O H
H2/Pt
HgSO4/H2SO4 markovnokov
H2O

H3C X X H
H3C H
1 mole X2/CCl4 HX HX
H3C H H3C H
X H markovnokovX
anti addition H X H
2 NaNH2/H2O
X2/CCl4 150oC
NaNH2/NH3
X X HX/R-O-O-R H X
Anti markovnokov H3C H
H3C H
R
H3C C- Na+ O3/(CH3)2S -O- H X
X X H3C H X/R-O
Or H

KMnO4,warm, X
CH3CH2X H
conc/OH-
SN2, works just with a
primary

HO OH
H3C
O+ O
H3C H

2
Reaction of Aromatic compounds

Br

NO2

H2/Ru
100oC, 1000 psi
Br2/FeBr3
O HNO3/H2SO4

SO3H
O SO3/H2SO4
R
R Cl , AlCl3 H2O, heat

Ketone (CH3)3C-Cl
Friedel-Craft acylation CO/HCl AlCl3 Or
AlCl3/CuCl (CH3)3C-OH
H2SO4 Or
(CH3)2C=CH2 C(CH3)3
O HF

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 Zn/Hg
reduction HCl
O Br

KMnO4 conc,hot Br2/hν

OH
H2O
oxydation

(CH3)3CO-,Na+
excess Cl2/hν SN2
or SN1
Nu-
H2/Pd
Nu
Cl
Cl
Cl
+ Br-
Cl Cl