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The electron
config of
carbon
This new hydrocarbon isolated by Michael Faraday in 1825
presented a huge problem.
.
The % of carbon was 92% Carbon (C= 12) . Its
relative molecular mass was 78.
Calculate the molecular formula
The molecular formula is C6H6 suggesting that the molecule
contained a large number of double bonds.
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 Kekulé’s 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 Kekulé
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
1.2-dimethyl
benzene 1,4-dimethyl benzene
1,3-
dimethylbenzene
2-hydroxybenzoic
acid
benzene-1,4-dicarboxylic
acid
phenyamine
chlorobenzene
nitrobenzene
Methyl 3-nitrobenzoate
2,4,6-trichlorophenol
phenyl ethanoate
phenylethanone
phenol
Benzoic acid
phenylethene
Fused ring systems