a.

REACTIONS OF AMIDES
(i) Basicity
Amides are only very weakly basic. As a result amides do not react with
mineral acids to form salts.

Amides show no measurable basicity due to the delocalized lone pairs of electrons on the
nitrogen atom.. Delocalization reduces an amide's basicity because the electron pair is not
associated with a single atom reducing the intensity and focus of its proton drawing ability.
Delocalization also helps to stabilize the overall structure of the amide.

NB: The lone pair of electrons on the nitrogen atom is less available for donation than the
pair on the nitrogen atom in amine.

(ii) Hydrolysis:
Amides are hydrolyzed when heated with dilute mineral acids or dilute alkali.

Alkaline hydrolysis of amides:

Example: If ethanamide is heated with sodium hydroxide solution, ammonia gas is given off and
you are left with a solution containing sodium ethanoate. This reaction is a distinguishing test of
ethanamide

(iii) Reduction:

Most amides can be reduced to primary amine by LiAlH 4 in dry ether. The number of carbon
atoms remain the same in both reactant and product.

RCONH2 LiAlH4 in dry ether RCH2NH2

CH3CONH2 LiAlH4 in dry ether CH3CH2NH2

 Ethanamide ethylamine

(iv) Reaction with bromine and Potassium Hydroxide solution( Hofmann

Degradation)

When an amide is warmed with bromine and concentrated alkali, a primary amine is formed in
which the length of the carbon chain is shorten by one carbon and thus descending the
homologous series

( Step down process)

Hofmann degradation is the reaction of a primary amide with a halogen ( bromine) in strongly
basic (sodium or potassium hydroxide) aqueous medium, which converts the amide to a primary
amine.

Example: CH3CH2CONH2 Br2/ Conc. KOH(aq)/heat CH3CH2NH2 + CO2

Propanamide (3C) ethylamine(2C)

ACTIVITY:

 Describe giving reagents and reaction conditions how you will convert propan-1- ol to
Ethyl amine.
(v) Dehydration:
Amides are dehydrated when heated with phosphorus(V)oxide to form nitriles.
RCONH2 P2O5 RCN + H2O
Example:
CH3CH2CONH2 P2O5 CH3CH2CN + H2O
(vi) Reaction with Nitrous Acid:
Amides react with nitrous acid in the cold to produce the corresponding carboxylic acids
and nitrogen gas. Nitrous acid is generated from the reaction of Sodium nitrite and HCl.
 Or
RCONH2 NaNO2/HCl RCOOH + N2(g) +H2O
(vii) Polyamides:
Polyamides are polymers which contain repeating amide, -CO-NH-, linkages.
Dicarboxylic acids and diamine react to form a polyamide. Polyamides are also
called nylons.
Proteins are examples of naturally occurring polyamides.

Example is nylon 6,6 which is prepared by mixing an aqueous solution of hexane-

1,6- diamine with hexane-1,6- dioc acid. When these two compounds
polymerise, the amine and acid groups combine, each time with
the loss of a molecule of water. This is known as condensation
polymerisation.

+
 [
] n

Nylon 6,6 is used in making fishing nets, racquet strings ,pocket combs, carpets,
clothing etc.