00:00
So, all carbon-carbon bonds
are actually an intermediate between a single
and a double bond. If you recall when we were
talking about mesomeric effects, right back
at the first module, we were talking about
the ability of a double bond to resonate throughout
a particular structure where more than one
double bond exists.
00:20
As you can see from the diagram shown here
at the bottom, you can see that we… that
it is possible for the double bonds to move
around in almost snake-like fashion. This
is due to the fact that the real structure
of benzene is a hybrid between these two resonant
forms; a standard carbon-carbon double bond
is shown here as 1.34 angstroms, a standard
carbon-carbon single bond is shown as having
a bond length of 1.5 angstroms. However, the
half way house length in benzene is 1.39 angstroms,
somewhere between the two, suggesting it is
not quite as long as a carbon-carbon alkane,
but not nearly as short as the conventional
carbon-carbon double bond.
01:05
So, the problem is that once these two structures
are effectively degenerate, you may have recalled
that phrase when we were talking about orbitals
because you can superimpose them, they are
also equivalent to make equal contributions
to the hybrid. However, the benzene structure
is badly represented in fairness by either
of these two examples structure one or two.
01:27
It actually has a structure which is an intermediate
between the two being more stable than both
of them. And so, what you will sometimes see
is a benzene ring… benzene ring being abbreviated
as effectively a hexagon with a circle in
the center such as that shown here on the
board.
01:43
The reality when we actually look at the orbital
system for benzene shouldn’t come as a huge
surprise. As you can recall from hybridisation,
you should be aware that SP2 hybridisation
correlates to the hybridisation of 1S and
2P orbitals. This results in a single P orbital
being unhybridised. And as you can see here,
each carbon on our benzene ring has that P
orbital which has been unhybridised… not
been hybridised.
02:14
And what this effectively allows to happen
is the electron in each of those is able to
delocalise around the entire ring structure
such as that which is shown on the diagram
in the top corner. As all of the carbon atoms
are SP2 hybridised, you effectively end up
with something which is a planar model…
molecule with bond angles of 120 degrees.
02:42
Contrast that, if you will, with the actual
structure and geometry of a cyclohexyl ring.
02:49
We haven’t necessarily covered that geometry,
but look it up. You will see it exists as
a chair or boat or somewhere in between, something
that forces the carbons and hydrogens to be
as far apart as possible to minimise steric
interference. Benzene rings, on the other
hand, are planar.