Alkenes

CH3

H3C

CH3

CH3
OH

H3C

OH

CH3 OH

CH3
H3C

H
OH
Anti markovnokov
CH3
H3C

OsO4/H2O2
Or
KMnO4/OH-

CH3
H

anti addition
H

CH3

X2/H2O

BH3/THF
H2O2/OH-

Syn addition

Syn addition

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

H3C

anti addition
H3C

CH3

markovnokov

O
Ph

CH3

HX
H3C

CH3
X

HX/R-O-O-R
Anti markovnokov

OOH

CH3 X
H 3C

KMnO4,warm,
conc

O3/(CH3)2S

H3C

CH3

Or

O3 /Zn/HCl

H3C

CH3
O

+ O
H

H3C

CH3

H3C
O+ O
H3C
CH3

O
OH

Alkynes

H3C

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

H3C

X2/CCl4

NaNH2/NH3

HX

H3C

H3C

H X
H3C

Anti markovnokov
C- Na+

O3/(CH3)2S

Or
KMnO4,warm,
conc/OH-

CH3CH2X

R
-OH X/R-O
H

H3C

SN2, works just with a

primary

H3C

HX/R-O-O-R

H
X

H3C

2 NaNH2/H2O
150oC

H3C
X

HX

markovnokov

markovnokovX

anti addition

H
O

HgSO4/H2SO4
H2O

1 mole X2/CCl4

BH3/THF
H2O2/OH- H C
3

H2/Pt
H3C

H3C

anti addition of H2

H H
H3C

H3C

OH

HO
O+ O

H3C

H
H X

Reaction of Aromatic compounds

Br
NO2

H2/Ru
100oC, 1000 psi
Br2/FeBr3

HNO3/H2SO4

SO3H
R

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

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

ED
ED

M/NH3
, ROH
M=Li, Na or K

EW

EW

Birch Reduction

Side chain reactions

O

Clemmensen
reduction

Zn/Hg
HCl

Br
OH

KMnO4 conc,hot
H2O

Br2/h

oxydation
(CH3)3CO-,Na+

excess Cl2/h

H2/Pd

SN2
Nuor SN1
Nu

Cl
Cl
Cl
Cl

+ Br-

Cl