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AMIDES
Amides are derived from carboxylic acids. A carboxylic acid contains the -COOH group, and in an amide
the -OH part of that group is replaced by an -NH
2
group.
-CONH
2
group.
The name is derived from the acid by replacing the "oic acid" ending by "amide".
The three simplest amides are:
HCONH
2
methanamide
CH
3
CONH
2
ethanamide
CH
3
CH
2
CONH
2
propanamide

The most commonly discussed amide is ethanamide, CH3CONH2

If the chain was branched, the carbon in the -CONH
2
group counts as the number 1 carbon atom. For
example:









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Physical properties
1) With the exception of methanamide, the amides are solids at RTP.
Methanamide is a liquid at room temperature (melting point: 3C
2) Amides have higher melting points than carboxylic acids having comparable Mr values because
the hydrogen atoms in the -NH
2
group are sufficiently positive to form a hydrogen bond with a
lone pair on the oxygen atom of another molecule. These hydrogen bonds need a large amount
of energy to break, and so the melting points of the amides are quite high.


3) The small amides are soluble in water because they have the ability to hydrogen bond with the
water molecules.
4) Amides are neutral compounds due to the delocalisaion of a lone pair of electrons on the
nitrogen atom which makes the molecule more stable. They are neutral to litmus and have
virtually no basic character at all - despite having the -NH
2
group.


MAKING AMIDES
Making amides from carboxylic acids
The carboxylic acid is converted into the corresponding ammonium salt.
For example, ammonium ethanoate is made by adding ammonium carbonate to an excess of ethanoic
acid.

When the reaction is complete, the mixture is heated under reflux to a about 200
0
C and the ammonium
salt dehydrates producing ethanamide.
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Ethanamide
The excess of ethanoic acid is there to prevent dissociation of the ammonium salt before it
dehydrates.
Ammonium salts tend to split into ammonia and the parent acid on heating, recombining on cooling. If
dissociation happened in this case, the ammonia would escape from the reaction mixture and be lost.
You couldn't get any recombination.
The dissociation is reversible:

The presence of the excess ethanoic acid helps to prevent this from happening by moving the position of
equilibrium to the left.

Making amides from acyl chlorides
A concentrated solution of ammonia in water reacts with the ethanoyl chloride at RTP to give
ethanamide and hydrogen chloride gas.



The hydrolysis of amides
Hydrolysis is a reaction with water.
There are two types of hydrolysis namely:
1) Acid Hydrolysis: amides are hydrolysed in the presence of dilute acids such as dilute
hydrochloric acid. The acid acts as a catalyst
If ethanamide is heated or boiled with a dilute acid (such as dilute hydrochloric acid), ethanoic acid is
formed together with ammonium ions.

NOTE :
Hydrochloric acid is acting as a catalyst in the reaction between the amide and water which would
produce ammonium ethanoate (containing ammonium ions and ethanoate ions). It is secondly reacting
with those ethanoate ions to make ethanoic acid.
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