Alkenes

CH3 H3C OH OH H CH3 H3C CH3

H CH3 H3C X H CH3 OH CH3

H OH Anti markovnokov CH3 H3C H H H CH3

OsO4/H2O2 Or KMnO4/OH-

Syn addition X2/H2O

H3C

anti addition
CH3 H CH3 OH
1)Hg(OAc)2/H2O 2)NaBH4/OH-

Syn addition H2/Pt

CH3 X H3C X H O H3C H 3C O CH3 H Ph OOH CH3

BH3/THF H2O2/OH-

H markovnokov

anti addition
CH3

H3C

X2/CCl4
H3C

CH3

HX markovnokov
H3C

H CH3

anti addition

HX/R-O-O-R Anti markovnokov

CH3 X
O3/(CH3)2S

KMnO4,warm, conc

H3C H H

CH3

Or
O3 /Zn/HCl

H3C O H3C + O

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

Alkynes
H3C H3C H H H H3C H H H H H H H H H H3C H
Syn addition of H2

H O Anti markovnokov H H O H

anti addition of H2

Syn addition

M/NH3 M=Li, Na orK

H2/Pd/BaSO4 quinoline Or Lindlar Catalyst

BH3/THF H2O2/OH- H C 3
HgSO4/H2SO4 H2O

H2/Pt
H3C X X
1 mole X2/CCl4

markovnokov
H H

H3C

HX

H3C

HX

X H3C X

H H H

anti addition
X2/CCl4
X X H X X H3C C- Na+
NaNH2/NH3

markovnokovX

2 NaNH2/H2O 150oC
HX/R-O-O-R

H X H3C H X H
R -OH X/R-O H

H3C

Anti markovnokov
O3/(CH3)2S

Or
KMnO4,warm, conc/OH-

H3C H

CH3CH2X SN2, works just with a primary

H3C

HO O+ O H3C

OH

Reaction of Aromatic compounds

Br NO2

H2/Ru 100oC, 1000 psi Br2/FeBr3

O O

HNO3/H2SO4

SO3H R

R Cl

, AlCl3

SO3/H2SO4 H2O, heat (CH3)3C-Cl AlCl3 Or (CH3)3C-OH H2SO4 Or (CH3)2C=CH2 HF

Ketone Friedel-Craft acylation

CO/HCl AlCl3/CuCl

O H

C(CH3)3

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 O KMnO4 conc,hot H2O

Zn/Hg HCl Br

OH

Br2/h

oxydation excess Cl2/h Cl

Cl Cl Cl Cl (CH3)3CO-,Na+ H2/Pd SN2 Nuor SN1 Nu

+ Br-