9. Anthracene(C14H10)
• Anthracene is composed of three fused benzene rings.
• It is colourless solid show blue fluorescence in UV light
• It is a component of coal tar. All carbon atoms are sp2
hybridized and ring has 14 pi electrons.
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10. Synthesis of Anthracene
1. Friedel-Crafts reaction.
From Haworth synthesis
From Benzyl chloride
From Benzene Methylene Dibromide.
2. Elbs Reation
3. Diels-Alder Reaction
11. When Phthalic anhydride in benzene solution is reacted with AlCl3 O-Benzoyl
benzoic acid is formed. This on heating with Conc,H2So4 Yield
anthraquinones which on distillation with Zinc dust give Anthracene
Haworth synthesis
From Benzyl chloride
Anthracene was prepared by condensation of two molecules of benzyl
chloride in presence of AlCl3.
CH2Cl
AlCl3
-2HCl
Bnzyl chloride Anthracene
2
O
HOOC
+
O
O
O
AlCl3
O
O
Zn dust
H2SO4
Benzene Phthalic anhydride 2-Benzoyl benzoic acd Anthraquinone
Anthracene
1. Friedel-Crafts reaction.
12. From Benzene Methylene Dibromide:
Anthracene can also prepared by reaction of benzene with methylene dibromide in
the presence of AlCl3
Anthracene may be synthesised by Diels Alder reaction involving 1,4-napthoquinone
and butadiene followed by oxidation of product with chromium trioxide in glacial
acetic acid and distillation with Zn dust.
2. Diels Alder reaction:
2 2 CH2B2
+
-2H
AlCl3
Benzene Methylene dibromide Anthracene
O
O
O
O
O
O
+
1,4-Napthaquinone
Butadiene
CrO3
Zn
Anthracene
SnCl4
-500
C
9,10 Anthraquinone
13. 3.Elbs Reaction:
A diaryl ketone containing a methyl group ortho to the carbonyl group E.g: o-methyl
benzophenone on pyrolysis gives anthracene
H3C
O
Pyrolysis
-H2O
O-Methyl Benzophenone
Anthracene
14. Reactions of Anthracene
• Electrophilic substitution reaction
• Other reactions
Oxidation, Reduction, dimerization.
17. Phenanthrene
• Colourless crystal obtained from coal tar.
• Its solution in benzene shows fluorescecne and is very reactive
in 9,10 positions.
• Carbons in Phenanthrene are SP2 hybridized and have 14 pi
electrons.
• It is isomeric with anthracene.
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