Structure of Benzene
Evidence against Kekules model of Benzene:
Discovered that all bond lengths are equal and all bond angles are 120.
Enthalpy change of hydrogenation of Kekules benzene much higher than experimental value.
Does not undergo electrophilic addition reactions such as bromination, as normal alkenes would.
Each carbon atom has 4 valence electrons, 3 of which are used in bonding (-bonds).
One valence electron occupies the p-orbital above and below the plane of the carbon atoms.
The electron in the p-orbital of one atom overlaps with electrons in the p-orbitals of adjacent
carbon atoms, resulting in a ring of electron density above and below the carbon atoms.
This overlap produces a system of -bonds spread over all six of the carbon atoms.
The
electrons are said to
be
delocalised
Nitration:
50C (for mononitration), Nitrating mixture of HNO3 and Conc. H2SO4
The sulphuric acid acts as a catalyst. It is needed to generate the nitronium ion, NO2+ from the nitric acid
HNO3 + H2SO4 NO2+ + H2SO4- + H2O
Halogen Carriers:
Bromination Fe, FeBr3, AlBr3
Chlorination Fe, AlCl3, FeCl3
The greater positive charge from the more powerful electrophile, X+, means the halonium ion is
able to attract a pair of electrons from the benzene ring so that a reaction can take place.