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Amines, Amides and Polyamides

Amines
As with alcohols you get primary, secondary and tertiary amines. But with amines, you also get
quaternary structures as tertiary amines still have a lone pair that can be lost to form a + charge on the
N:

Primary: one or no alkyl groups attached to the N

Secondary: two alkyl groups attached to the N

Tertiary: three alkyl groups attached to the N

Quaternary: four alkyl groups attached to the N

Naming amines
With the amine functional group you have the option of putting amino at the beginning of the name or
amine at the end.

For example:

the longest carbon chain is just one so it is meth. The meth part becomes methyl, and
if we put amine at the end of the name, we get methylamine.

Alternatively, you could call it aminomethane.

in this case we have two methyl groups so it becomes dimethylamine.

we have a 3 carbon chain, with the NH2 on carbon 2, so we would call it 2-


propylamine (the 2 refers to where the amine is) or 2-aminopropane.
We would call it tetramethylammonium chloride. The name ending is a little bit
different as it is now an ion.

if there is one thing to remember about amines it is lone pair. It is responsible for amines being
basic and nucleophilic.

Preparation
Nucleophilic Substitution

From halogenoalkanes

CH3CH2Br + NH3 CH3CH2NH2 + HBr

Reduction

NO2 NH2 using Sn/HCl (see benzene chemistry)

-CN NH2 using LiAlH4 (see carbonyl chemistry)

Properties

Basic

The main property that you need to know is that amines are basic, so in solution they have pH > 7 with
OH- being formed:

Solubility

Amines can form hydrogen bonds with water so you could say that they are soluble in water.

But it doesnt apply to all amines. If you increase the length of the alkyl chain, you are increasing the
length of the non-polar section of the molecule, which will decrease the solubility in water.

There is no definite rule as to when they become soluble versus insoluble. But any question on this
should be obvious one way or the other.
Reaction with acid
Amines are bases (a proton acceptor) due to the lone pair. A very popular reaction with examiners is
amine and acid. The amine picks up an H+ from the acid to form a salt:

How basic is it?


This is all to do with how available the lone pair is on the nitrogen, which depends on the groups
attached.

Alkyl groups strengthen the lone pair more basic

e.g. CH3NH2

Alkyl groups have a slight electron donating effect, resulting in a more basic amine. The more alkyl groups
there are, the stronger the effect, for example:

CH3NHCH3 is more basic than CH3NH2

Benzene has the opposite effect and will pull electrons away from the lone pair, weakening it, resulting
in a less basic amine.

Benzene pulls electrons away from the nitrogen less basic

Below we can see the order of basicity for three different amines, with CH3CH2NH2 being the most basic.
NH3 is in the middle as it only has hydrogens attached to the N, so the lone pair isnt strengthened or
weakened:

CH3CH2NH2 > NH3 > Ph-NH2

Amides
Students get amines and amides mixed up all the time. Probably because they have similar names and
also look quite similar structurally:
The big difference is that an amide has a carbonyl group, which means that:

amides are not basic or nucleophilic

The lone pair can be delocalised on to the oxygen of carbonyl group, which means that the lone pair is
not available.

Therefore amides are not reactive. They are made or broken and thats about it.

Amide Preparation
Amides are usually made similarly to esters i.e. condensation reactions. In this topic they seem to make
them from acyl chlorides:

Amine + Acyl Chloride Amide + HCl

Polyamides
Similar to polyesters in the carboxylic acid topic, we can make polyamides.

We just need two NH2 groups and two carboxylic acid groups (or acyl chlorides) (these are the
monomers).

In this example, the product has an acid group at one end and an amine group at the other, therefore it
can do the same reaction again and again.and again. The reaction is simply the removal of water.

You can of course replace the acid with an acyl chloride and do the same reaction (removal of HCl).

To form the amide, all you have to do is remove an H from the NH2 and the OH from the acid to form the
H2O.
Polymer

Similar to what we saw with the polyesters, we draw polyamides with the brackets and the little n:

Repeat unit

And similarly for the repeat unit, just leave out the brackets and the n:

Breaking the polymer (hydrolysis)


This is very similar to the carboxylic acid tutorial.

The bond formed when making the amide is the C-N bond, therefore this is the bond that is broken in
hydrolysis:

As the diagram shows, you need to add the OH to the carbonyl group, the H to the NH group and break
the C-N bond.

Conditions

Under acidic conditions the amine formed will react with the acid:
Under alkaline conditions the carboxylic acid formed will react with the base:

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