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Aromatic Compounds
non-polar Molecule
insoluble in water
This did not explain why the structure was so unreactive, the
chemists of the time were convinced that it should react with
bromine in the dark at room temperature. This does not happen
with benzene.
This does not fit with Kekuls idea of alternating double and single bonds.
Another problem was the energy of hydrogenation (addition of hydrogen).
The hydrogenation of cyclohexane is well known.
So if three double bonds are present as in benzene, then the
comparable reaction should liberate 3 times that of cyclohexane.
-(3 120) = - 360 kJ mol-1
But the actual value for benzene was found to be different. -208kJ
mol-1
-360kJ/mol (3
X 120)
-208kJ/mol
progress
This is a better all round model than the Kekul
structure which shows 2 extremes of the same
thing. The circle in the middle shows the
delocalisation of the aromatic system.
The bond length of C-C bonds in benzene are found
someway between that of an alkane and an alkene.
C-C 0.154
cyclohexane
C=C 0.134
cyclohexane
C-C in benzene 0.140
Evidence for delocalisation in benzene
ortho Y
(or 1,2) meta
(or 1,3) para (or 1,4)
NO2
Br
NO2
17
Naming benzene molecules
1.2-dimethyl benzene
(ortho-dimethyl benzene) 1,4-dimethyl benzene
(para-dimethyl benzene)
1,3-dimethylbenzene
(meta-dimethyl benzene)
Common Names of Subs. Benzenes
CH3 OH NH2
O anisole O O
styrene
C C C
H OH CH3
CH3
benzaldehyde benzoic acid acetophenone
C N CHCH3
benzonitrile cumene
Fused ring systems