00:01
So let's have a quick look at what I mean.
00:05
Let's take, for example, our carbon. I've
shown here an sp2 hybridized orbital (you
should recognize that: big fat green lobe,
very small orange lobe), and I've shown another
carbon on the other side on the board. And
as you can see, these two hybrid orbitals
can overlap to form a sigma molecular orbital.
And, as I said to you before, pi bonds are
formed after sigma bonds are formed. And as you
can see, pi bonding is possible because we
also have the unhybridized py atomic orbital
from each carbon able to overlap as long as
those lobes are in the right phase. This gives
rise to a rather interesting sort of hot dog
/ sausage structure that you can see there,
where you have a sigma bond shown in green in
the center and you have a pi bond which is
stacked on one either side.
01:00
So the last part of this is where I want to
talk to you a little bit about alkynes, or
triple bonds. And I explained to you that
the shapes of some organic molecules can be
explained by hybridization. And I want to
draw to your attention one final example,
and that is ethyne. Now if we look at ethyne,
which is otherwise known as acetylene (the
actual use of which is mostly in welding torches,
but there are a wide variety of other things
that can be done with it) is that we actually
have three bonds in the center. Now we know
how we can get two: sigma and pi bonds. However,
ethyne is a linear molecule. It is not trigonal
planar; it is not tetrahedral. All of its
bonds are in a line, and why is this? So let's
go back to our hybridization. Let's look at
carbon. Prior to hybridization, we have two
electrons in the 2s, two unpaired in the 2p.
However, when it comes to triple bond formation,
we only hybridize two of those orbitals, and
this gives rise to so-called sp hybridization.
02:13
Looking across, you can see you've got two
unpaired electrons in the hybridized orbitals,
and you have two unpaired electrons in the
non-hybridized orbitals, the 2p. The sp orbitals
have a linear geometry with the p orbitals
at right angles. So instead of being one over
the top and one along, you have one bond over
the top, another in this direction, and also
one along. Hopefully, you can see that in
the diagram shown here. Here I've shown the
z and I've shown the y axes. Those z and y
axes are where you would see the p orbitals
engaging in one pi bond and then a second
pi bond 90 degrees from the first.
03:02
Sp orbitals will make sigma bonds either to carbon
or hydrogen, and the p orbitals will overlap
to give two perpendicular pi bonds. And this
is the origin of the triple bond. And in a
triple bond, of course, that means we have
six electrons in total: two in the sigma and
two each in each of the pi bonds that are
formed. Hybridization and bonding in molecules
doesn't just affect the geometry, that as
you might imagine, it also affects bond energies
and bond lengths. And here is a table, shown
on the board, which indicates how compounds
which are similar to each other have different
strengths in bonds and different bond lengths,
depending on the degree of hybridization and
the types of bonds that are formed. In the
first instance, we see ethane with a single
sigma bond. The strength of this bond shown there
is 376 kJ per mole. The second double bond,
higher in energy of course, but it is not
twice the strength of the original sigma bond.
Equally, when we add a further pi molecular
bond to this in the form of an alkyne, such
as ethyne shown here, we again see an increase
in the strength of that bond. But notice the
gap between those two types—so between the
single sigma, the double, and the triple bond.
Notice the difference in strength and the
difference in length. They do not go up as
you would expect. And this is because as you
add additional electron density across that
system, you're weakening the bond and leaving
it more prone to being broken open via reactions—reactions
which we'll come on to in future lectures.