As
soon as we try to make a localized MO model of benzene, we run into
trouble. The planar hexagonal geometry of the molecule, with 120
bond angles, suggests sp2 hybridization around the carbons, with
one spl orbital from each C pointed toward an H, and the other two
directed toward the neighboring carbon atoms in the ring. This skeleton
of s bonds uses 24 of the 30 bonding
electrons (6 X 4 from carbons plus 6 x 1 from hydrogens), and all
of the outer orbitals except the six p orbitals perpendicular to
the plane of the hexagon. This s framework
is shown. What should be done with the six unused electrons and
six remaining p orbitals? These are shown in perspective at the
bottom left. Adjacent p orbitals could be combined in pairs around
the ring to make every other carbon-carbon bond a double bond. There
are two ways of doing this, represented schematically below. These
are known as the Kekule structures after the man who first proposed
them, but they cannot be correct because we know that all of the
carbon-carbon bonds are the same length. A somewhat less plausible
way of pairing the p orbitals would be to connect two across the
ring, and then pair the remaining two at either side, as in the
three Dewar structures shown below the Kekule rings.