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Primary amines, like ammonia can act as bases. The lone pair of electrons on the
nitrogen atom of ammonia and amine molecules is a proton (H+ ion) acceptor.
Amines react readily with acids. The lone pair on the nitrogen rapidly accepts a proton
from an acid to form a substituted ammonium salt.
When ethylamine vapour reacts with HCl gas, the product is ethylammonium
chloride. This forms as a white smoke which settles as a white solid.
CH3CH2NH2 (g) + HCl (g) CH3CH2NH3+Cl- (s)
Preparation of amines
Preparing aliphatic amines
An aliphatic amine can be prepared by heating excess ammonia in ethanol. Ammonia acts as
a nucleophile during the reaction. The initial product is a salt of the amine. The free amine can
be liberated from its salt by adding dilute sodium hydroxide.
Preparing Aromatic Amines
First nitration to make a nitro compound, then reduction to form the amine
The reduction of the nitro-amine is achieved by boiling under reflux with tin and
concentrated HCl. The aromatic amine dissolves in excess concentrated HCl forming a salt.
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The free amine can be liberated from the solution by adding NaOH solution and is then
separated from the mixture by steam distillation.
Synthesis of Azo Dyes
First an aromatic amine must be reacted with Nitrous Acid (generated in situ from
NaNO2/HCl) at less than 100C. This forms a benzene diazonium salt.
The positive charge on the N N+ group means that the diazonium ions are strong