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AMINES
Introduction
Amines are one of the most important groups of organic nitrogen containing compounds. They can
be regarded as derivatives of ammonia in which one or more of the hydrogen atoms in NH3 is
substituted. We get a compound of the form RNH2, called a primary amine, e.g. CH3CH2NH2,
ethylamine.
Free amines are relatively rare in nature, but they do occur in decomposing protein such as meat
and fish. Normally the NH2 group is associated with other functional groups and in this respect it
forms an important part of proteins. Compounds containing the NH2 group are important in the
manufacture of drugs, dyes and nylon.
The intention of this practical is consider the properties of an alkylamine (butylamine) and
arylamine (phenylamine) and to compare their properties with those of ammonia. Butylamine is chosen
because it is a liquid and not too volatile. Phenylamine is also a liquid, colourless when pure, but the
sample you use is likely to be dark-coloured due to atmospheric oxidation.
Caution! Phenylamine is toxic and harmful because of skin absorption. Avoid all skin contact.
Butylamine is an irritant and is extremely flammable. You should manage your apparatus in good
order.
Chemicals
Universal indicator paper, butylamine (or propylamine), phenylamine, ethanoyl chloride, phenol, 2naphthol, bromine water, ice, ammonium chloride, sodium nitrate(III) and concentrated hydrochloric
acid, Bench solutions: ammonia, hydrochloric acid, sodium hydroxide and copper(II) sulphate(VI).
Procedure
Experiment 1
Shake 2 drops of butylamine and 2 drops of phenylamine separately with 2 cm3 of water. Now test
each of these solutions and a solution of ammonia with universal indicator.
Experiment 2
1. Shake 2 drops of butylamine and 2 drops of phenylamine separately with 2 cm3 dilute
hydrochloric acid.
2. Add dilute sodium hydroxide to the solution of phenylamine in hydrochloric acid until the
mixture is alkaline.
3. If you carry out this experiment with ammonia, you may have a good contrast.
Experiment 3
1. Add ammonia solution dropwise to 2 cm3 of copper(II) sulphate solution until the ammonia is
present in excess.
2. Repeat the experiment using first butylamine and then phenylamine in place of ammonia solution.
Experiment 4
Ammonia and amines can act as nucleophiles in attacking the positive centres in molecules such
as ethanoyl chloride, CH3COCl and benzoyl chloride, C6H5COCl. For example, ammonia reacts very
vigorously with ethanoyl chloride forming ethanamide.
Butylamine
Ammonia
N.A.
N.A.
N.A.
Analysis
Give equations for all the above reactions. You should give structures for some of the above
experiments.
2.
3.
4.
5.
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7.
8.
Comment the solubility of the amines in water and account for any differences in solubility.
Comment the basic strength of the amines relative to ammonia and account for any differences in
their strength as bases.
Explain the different solubility of phenylamine in water and in dilute hydrochloric acid. [Given
equation if necessary.]
Propose a reaction mechanism for the reaction between benzoyl chloride and butylamine.
Compare and explain the reactivity of ammonia, butylamine and phenylamine towards benzoyl
chloride.
Comment the stability of the three diazonium salts.
Bromine water reacts with phenylamine instead of benzene. Explain.