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AROMATICITY

Aromatic Compound Anti Aromatic Compound

1.Cyclic. 1.Cyclic.
2.Planar (sp2 or sp). 2.Planar (sp2 or sp).
3.Completely conjugated. 3.Completely conjugated.
4.It must follow Huckel’s rule: 4.It must follow Huckel’s rule:
[4n+2]e– [4n]e–
(where n can be 0,1,2,3,…..) (where n can be 1,2,3,…..)
Example: Example:
If n=0 2electrons If n=1 4electrons
n=1 6electrons n=2 8electrons
n=2 10electrons n=3 12electrons

Non Aromatic Compound: Compounds which are neither aromatic nor


anti aromatic are called non aromatic.
AROMATICITY

Stability Order :-
Aromatic compound > Non aromatic compound> Anti aromatic compound

NOTE :- Anti aromatic compounds are highly unstable and do not exist at room
temperature and having tendency to make dimer.

Cyclobutadiene
AROMATICITY

Q. Find out whether the compound is aromatic, anti aromatic or


non aromatic.

(Benzene)

(Cyclopropenyl cation)
AROMATICITY
AROMATICITY

(Cyclopentadienl
carbanion)

(Cyclopentadienyl
carbocation)
AROMATICITY
AROMATICITY

(Tropylium cation)
(Cycloheptatrienyl cation)
GENERAL ORGANIC
CHEMISTRY
AROMATICITY

(Furan)

(Thiophene)
AROMATICITY

(Pyrrole)

(Pyridine)
AROMATICITY

[10]Annulene Ring adopts a non planar


geometry to minimize repulsion
Annulenes-Monocyclic hydrocarbons containing alternate single bond and
double bond.

(Cyclooctatetraene) Tub shaped


[8]Annulene (Non planar)
AROMATICITY

Polycyclic fused compound

(Naphthalene)
Benzenoid aromatic compound

(Anthracene)
Benzenoid aromatic compound
AROMATICITY

(Phenanthrene)
Benzenoid aromatic compound

(Azulene)
Non-benzenoid aromatic compound
AROMATICITY
AROMATICITY
AROMATICITY

(Tropone)

(Tropolone)
AROMATICITY
AROMATICITY

Applications of Aromaticity :

Q. Which of the following compound is more acidic ?

(a) (b) (c)

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