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PHENANTHRENE
Presented By
Basanta Rajkhowa
Conditions necessary for aromaticity
4..Obey Huckle rule which state that any aromatic compound must
contain 4n+2 pi electrons where n =
0,1,2,3,…
Polynuclear Hydrocarbons
Linear Angular
Fused Ring Aromatic Hydrocarbons
* Each carbon atom also possesses a p orbital and this are perpendicular
to the plane containing the sigma bonds. Lateral overlap of these p
orbitals produces a pi-molecular orbital containing 14 electrons.
5 8 1
1
6
7 2
7 10
6 5 4 3
8 9
Synthesis of Phenanthrene
1.Haworth Method
COOH
2.Pschorr Synthesis
Cu
3.Bardhan –Sengupta Synthesis
Br MgBr CH2CH2OH CH2CH2Br
O
Mg 1.H2C CH2 HBr
ether 2,H3O +
O
O O O O
OC2H5
+
CO2C2H5 CH3CH2ONa - CO OC2H5
CO2C2H5 -EtO-
O
CH2Br CO2C2H5
H2C
H 1.KOH
2,HCl
C2H5O2C K 3.heat Na
+
O
SN2 O Moist ether
O
P2O5
Se
OH cyclisation
Physical Properties Chemical Properties
Cl2
in CCl4 -HCl
9,10-Dichloro-9,10-
Dihydrophenathrene 9=Chlorophenanthrene
2.Friedel Crafts Acylation
Phenanthrene undergoes acylation on treatment with acetyl chloride in
presence of aluminium chloride at 273 K to give 9-acetylphenanthrene
O
H3C C
O
AlCl3
+ H3C C Cl
273 K
Acetyl chloride
9-Acetylphenanthrene
3.Nitration:
O2N
HNO3
H2SO4
9=Nitrophenanthrene
4.Sulphonation:
conc. H2SO4
SO3H +
SO3H
2-Phenanthrenesulfonic acid
3-Phenanthrenesulfonic acid
Oxidation:
O
K2Cr2O7 H2O2 COOH
H H
Na/C5H11OH
9,10-dihydrophenanthrene
Preparation of Derivatives
1.Preparation of 1-alkylphenanthrene
O
O
COOH
AlCl3 Zn-Hg/HCl
+ O
Naphthalene O
COOH 1) RMgX OH
conc.H2SO4 O 2) H2O
R
Se
2.Preparation of 4-alkylphenanthrene
O
O
HO
HO
O AlCl3
+ Zn/Hg + HCl
O O
O
succinic anhydride
CH3
O
IMgO
H3C
Pd-C
3.Preparation of 2 or 3-alkylphenanthrene:
. By using alkyl succinic anhydride instead of succinic anhydride, an alkyl group
can be introduced into the 2- or 3- position. For example, preparation of 2-
derivative
O R
O
R COOH
AlCl3 Zn-Hg/HCl
+ O
Naphthalene O
R R R
COOH
conc.H2SO4 O Zn-Hg/HCl
Se
Uses: