10.

1 Introduction to Benzene
Diagram 1:
Full structural formula of benzene

Benzene's other name is 1,3,5-cyclohexatriene. It is a ringed structure and not a straight

chain structure and so has the prefix cyclo. Another name for the structure as a whole is the
Kekule Structure. The double bonds on carbons 1, 3, and 5 are alternating meaning that they can
also occur on carbons 2, 4, and 6. Examination of the properties of the bonds formed in the
benzene molecule are ambiguous as can be seen in the table below.

*strange bonds in benzene

length

strength

154 pm

346 kJ mol

134 pm

614 kJ mol

140 pm

507 kJ mol

So, this leaves us with the question: what the heck kind of bond is going on in the
benzene? The answer to that is found in the diagram below which represents a 1.5 bond. Not a
double bond, not a single bond, but an in between kind of bond: the 1.5 bond represented by a
solid line and a dashed line.
Diagram 2:
Representing the bond

The circle represents the constantly alternating bonds.

Diagram 3:
Further visual representation of the skeletal structure

In the skeletal structure, the edges represent a single carbon and the straight solid lines
represent a single bond and the circle represents the constantly alternating double bonds.
Diagram 4:
Substitution occurring with benzene ring

It is important to note that even though substitution may occur with benzene, addition
does not make an appearance as it is quite difficult to break the ringed structure and add other
compounds. So, in short, substitution yes but addition no. In addition, benzene is more stable and
less reactive and it is therefore harder to break that ring.
Benzene is also aromatic meaning that it induces an aroma or smell or scent and it is also
unsaturated as there are CC double bonds present in its structure.

HL
The pz orbital is perpendicular to the plane of the molecule and when they hybridize they
make a classic ring structure. Specifically, they make two rings: one above the molecule and one
below the molecule. And it is these delocalized electrons in the ring that give the ring the extra
stability which makes breaking the ring unlikely.

Credits go to Richard Thornley as these notes were based upon his videos