Unit # 13

PREPARATION OF NAPTHALENE

BS 2ND year 3RD SEMESTER

ORGANIC CHEMISTRY

Dr. Farkhanda Hassan

Assistant Professor
Dept. of Chemistry Fuuast
Formula :C10H8 ,
M. Point: 80.26c
B.Point: 218c
M Mass: 128.1705g/mol
Density : 1.14 g/cm3
It is the simplest polycyclic aromatic hydrocarbon, and

is a white crystalline solid with a characteristic odor

that is detectable at concentrations as low as 0.08 ppm

by mass. As an aromatic hydrocarbon, naphthalene's

structure consists of a fused pair of benzene rings.

 History
In the early 1820s, two separate reports described a
white solid with a pungent odor derived from
the distillation of coal tar.

In 1821, John Kidd cited these two disclosures and then

described many of this substance's properties and the
means of its production
He proposed the name naphthalene, as it had been
derived from a kind of naphtha (a broad term
encompassing any volatile, flammable liquid hydrocarbon
mixture, including coal tar) Naphthalene's chemical
formula was determined by Michael Faraday in 1826. The
structure of two fused benzene rings was proposed
by Emil Erlenmeyer in 1866, and confirmed by Carl
Gräbe three years later.
Synthesis of naphthalene
Benzene + ( Succinic anhydride )( 4-oxo,4-phenyl
butanoic acid
 Benzene +succanic anhydride

NEPTHLINE
Benzene +acetic anhydride

(4-ph-tetranone) (3-benzoyl propanoic acid )or

beta benzoyl prppanoic acid
 STRUCTURE AND REACTIVITY
* Naphthalene is the derived from two fused benzene
ring.
* C=C bond length are not same in naphthalene.
* Naphthalene gives electrophilic aromatic substitution.
* Many electrophilic aromatic substitution naphthalene
react under mild condition
* Example both naphthalene &benzene react with Cl2 in
presence of AlCl3,FeCl2.
* Similarly both benzene & naphthalene can be alkylated
by using fedral crafts reaction.
 Reactivity of naphthalene
 Naphthalene is more reactive than benzene, both
in substitution and addition reactions, and
these reactions tend to proceed in a manner that
maintains one intact benzene ring.
The alpha position is more proton to
reaction position in naphthalene because the
intermediate formed becomes more stable due
to more diffusion of charges through the adjacent pie
electrons. Thus resonance do have its role to play
in reactivity of alpha position.
D0ubble bond character & Bond length

Different C-C bond length revealed the decrease

aromaticity of fused poly nuclear aromatic hydrocarbon

1.422oA
 Resonating structure

Five resonating structure two structure(A,B) complete

benzene ring
Resonance structure
 Reactivity of naphthalene

Reactivity As Resonance energy Stability of the compound increase

decreases increase

Resistance to destroy aromatic character increase

 Conclusion
 Naphthalene under goes eletrophilic
substitution at C-1 position. Carbocat ion &
transition state resulting from attack at 1
position are much more stable then those
resulting from position 2 there for position
1 is prefer able
 Reference
1. Organic Chemistry 6th edition by John McMurry .

2. Organic chemistry 6th by Boyed & Morrisons

3. Organic chemistry by BS BHAL

4. Internet Explore
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