00:02
In terms of nomenclature, the names are given
by replacing the “–e” at the end of
the corresponding alkene with the appropriate
suffix. So, let us take a look, for example,
at acid or acyl chlorides. In this particular
example, as you can see, what we have is a
chlorine group directly attached to the carbonyl
carbon. In terms of the number of carbons
we have, we have ethyl, do we not? And so,
therefore, this will be known as ethanoyl
chloride. Sometimes in common parlance, it
is called acetyl chloride and is a very common
reagent when acetylation reactions need to
be carried out.
00:40
Let us look at the longer chain and slightly
more complicated acid chloride, shown on the
right hand side of the screen. Here, you can
see the longest chain consists of 4 carbons.
00:51
Therefore, it must be a butanoyl chloride
of one description or another. Note also,
the numbering goes as before, the order of
priority is the carbon which bears the oxygen,
oxygen having a larger mass than the carbon
it takes priority and we count backwards along
the longest chain: 1, 2, 3, 4. Therefore,
our 2 methyl substituents are in the 2 position
and the full IUPAC name for this molecule
would be 2,2-dimethylbutanoyl chloride.
01:23
Now, let us talk about anhydrides. Anhydrides
have these rather interesting structure where
we effectively have the joining of two carboxylic
acids in the absence of water. Hence, the
name acid anhydride, so in other words,
acids with their water removed. In this particular
case, all of these assuming they are uniform
would take the name of the alkane group with
the “-e” removed and would be “-ioc”
and then anhydride.
01:54
So, in this scenario, because we have two
ethanoyl or ethanoic systems coming together,
it would be an ethanoic anhydride. If, indeed,
we had a third carbon on each of those, it
would be propionic anhydride. The common name
for ethanoic anhydride is acetic anhydride
and you will sometimes see that on bottles
of chemicals.
02:18
Now, I want to talk to you about carboxylic
esters and esters are very important, not
just in terms of a, from a medical perspective,
in terms of product development, but also,
for example, in the flavours that you get
in things like wine and odours and so forth that are
derived from complex arrangements of carboxylic
esters.
02:41
The nomenclature for an ester is shown here.
Here, we start off with the idea that the
names must be alkyl alkanoate which means
that when you look at Methylethanoate, we
find the part of the molecule which contains
the carboxylate part i.e. that has the CH3
directly attached to the carbon, could be
a CH2 or a CH, but is directly attached to
the carbonyl carbon. That is your “-oate”
part.
03:10
So, in this case, we have a CH3 and then a
carbon, therefore, it is ethan; it must be
ethanoate. The alkyl part is derived from
the alkyl or aryl chain which is directly
attached to the oxygen. So, looking at the
right hand side of that molecule methylethanoate,
you can see that there is a CH3 group. This
is methyl and therefore, the name for this
compound is methylethanoate.
03:37
Have a look at the molecule in the right hand
side and see if you can apply those rules
to determine the name of that molecule. Let
us work through it.
03:50
If you actually have a look at what contains
a carboxylate moiety, our carbon double bonded
oxygen, we count backwards: 1, 2, 3, 4, 5
through our longest possible chain. This gives
us the core structure, if you like, pentanoate.
And now, what we have to do is see the length
of the chain that’s directly attached to
the oxygen, the alkoxy part, counting along
from the oxygen: 1, 2, 3, we have 3 carbons
on the right hand side and therefore, our
underlying structure, without any further
substituents, is propylepentonoate. This gives
us the basic structure.
04:29
The substitution in the pentonoate chain is
correlated by knowing that we go from 1, 2,
3, 4, 5 all the way through the alkanoic part
of that molecule. And so, therefore, the methyl
groups are in the 2 and 4 positions respectively,
thus giving us the name 2,4-dimethyl-propylpentonoate.
04:48
Now, let’s look at the final class and this
is a particularly important class because
as we will see in Module IV, amides and esters
pervade every element of drug development and
drug design, if not least, from a product
perspective. Amides consist of a carboxyl
group to which carbonyl… carbonyl carbon
and NH2 or NR2 group is attached. So, let’s
have a look at some of this nomenclature.
05:22
Here we have a very simple, so called, primary
amide, there aren’t many of them. This is
ethyl amide. This is because the carboxyl
part which forms the initial… the initial
part or initial prefix for the nomenclature,
it contains two carbons: ethyl amide, otherwise
known as acetylamide or acetamide.
05:44
Now, let’s have a look at something a little
bit more complex on the bottom right hand
side. This does look a bit more complex, but
the reality is quite straightforward. Let
us look at the underlying amide, let’s have
a look at the longest chain in the system,
okay?
So, if we count back from our carboxyl group
like we did for our ester, we see that we
have 3 carbons as our longest chain. So, this
means that we are talking about a propanamide
that is the longest chain, that is the underlying
carboxyl part of it. But, wait, not only do
we have substitution along that propanamide
ring, but we also have substitution directly
on the nitrogen. Hence, the term N,N-trimethyl…
N,N,2-trimethylpropanamide because we are
saying, by that nomenclature, that we have
2 methyl groups attached to the N and we also
have a methyl group in the 2 position on the
propane chain. If we didn’t have those 2
methyl groups on that nitrogen, it would just
be 2 methylpropanamide, but because we have
those 2 methyl groups on that nitrogen, we
have to designate where they are.
07:00
Right. Okay. So, nomenclature summary because
that was a lot to get through. If we look
here at functional group carboxylic acid,
in all cases, we change the “-e” at the
end of the alkene… alkane to the “-ioc”
acid, the “-oyl” chloride, the “-oic”
anhydride, the alkyl “-oate” or indeed,
the amide depending on whether we are dealing
with a carboxylic acid, an acyl chloride,
an anhydride, a carboxylic ester or an amide
itself.
07:34
So, this is the nomenclature summary. And
so, when you see these names, you should be
able to relate them directly to the basic
structure of that functional group and this
is important because understanding the basic
structure of that functional group means you
will know how it will react with other things
and this is what we are going to go on to
now.