00:01
So here we have a couple of other examples
of resonance. This is an allylic structure.
00:06
And for resonance to occur, there needs to
be a group donating and a group accepting
a pair of electrons. In this case, we can
move the double bond – the carbon to the
carbon, that’s a pi bond – and form another
carbon-carbon pi bond. In this case, the positive
charge moves from one carbon to the other,
the reality being of course that we wouldn’t
be able to detect this, we wouldn’t be able
to see this. But this is the inherent stability
of this allylic carbo-cation. The pi bond
is the donor and the positively-charged carbon
– or carbo-cation – is the acceptor. Normally,
carbon does not necessarily form an ion, by
which I mean it does: it’s just not very
stable. So what tends to happen is it tends
to react relatively quickly with something
from which it can obtain electrons. So therefore
our awareness of the existence of resonances
is related to the apparent stability of something
which, on the face of it, is thermodynamically
unstable.
01:12
Another example of resonance is in the carboxylate
ion. And we’ll come onto carboxylates when
we talk more about the organic chemistry.
Note though what we’re doing is we’re
moving a negative charge to convert a single
carbon-oxygen bond into a double carbon-oxygen
bond and we’re placing a negative charge
on the adjacent oxygen.
01:32
Now of course the reality is that these electrons
are moving back and forth, back and forth
all the time. The net result is that the typical
way of drawing it, as you can see here shown
after the equivalent (≡) sign, is that the
electron density of that negative charge is
distributed evenly between the two carbon-oxygen
bonds. Again, it’s not something that you
can isolate but it’s something that you
can observe by virtue of knowing or being
aware of acidity and knowing that this carboxylic
acid is actually more acidic than it actually
should be by virtue of the stability imparted
by that resonance. O- does not typically
form unless the charge can be stabilised.
In this case, the charge is stabilised by
resonance.