BACHELOR OF SCIENCES HONS IN BIOSCIENCE WITH

CHEMISTRY

NAMES: ANUSIA A/P THEVENDARAN

ID:17WLR00332
COURSE TITLE: BACH1623 ORGANIC CHEMISTRY
EXPERIMENT: 7 ( Reactions of amines)
Objective: To observe the chemical properties of butylamine, phenylamine and ammonia.
To compare them with the properties of ammonia.
Introduction:
Amines are one of the most important groups of organic nitrogen containing compounds. Amines
can be regarded as derivatives of ammonia in which one or more of the hydrogen atoms in NH3
is substituted. In primary amines, only one of the hydrogen atoms in the ammonia molecule has
been replaced. For example, the simplest amine, CH3NH2, can be called methylamine. In a
secondary amine, two of the hydrogens in an ammonia molecule have been replaced by
hydrocarbon groups such as dimethylamine. n a tertiary amine, all of the hydrogens in an
ammonia molecule have been replaced by hydrocarbon groups, for example trimethylamine.
Free amines are relatively rare in nature, but amines do occur in decomposing protein such as
meat and fish. Normally the –NH2 group is associated with other functional groups and 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 considered 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.

Apparatus: Safety spectacles, Protective gloves, 6 test-tube with corks, test-tube holder and
rack, wash-bottle of distilled water,3 watch-glasses,pH paper and glass stirring rod and spatula.
Chemicals:Phenylamine, butylamine, Ammonia solution 2M NH3, Concentrated hydrochloric
acid, copper(II) sulphate solutions 1M CuSO4, bromine water and ammonia chloride.
Procedure:
(A) Solubility in water.
1. 2 drops of phenylamine and 10 drops of water was added into a test-tube and was
shake.
2. The pH paper was immersed into the mixture. The observation was recorded in a
table 7.
3. Steps 1 and 2 was repeated using butylamine instead of phenylamine. The pH of
ammonia solution was tested.
(B) Reaction with hydrochloric acid
1. 5 drops of phenylamine and 5 drops of water was added into a test-tube and was
shake.
2. Concentrated hydrochloric acid was added drop by drop into phenylamine solution.
3. The contenst of the test-tube was poured on the watch glass in fume cupboard. The
observation was noted.
4. Steps 1 to 3 was repeated using butylamine.
5. Steps 2 and 3 was repeated by started with 10 drops of ammonia solution.
(C) Reaction with copper(II) sulphate solutions
1. 2 cm3 of copper(II) sulphate solutions was added into a test-tube.
 2. Phenylamine was drop by drop and the mixture was shake all the time until
phenylamine is present in excess. The observation was noted.
3. Step 1 to 2 was repeated with butylamine and aqueous ammonia.
(E)Reaction with bromine water

1. 5 drops of phenylamine and concentrated hydrochloric acid dropwise was added into
a test-tube until obtain a clear solution.
2. 1 cm3 of bromine water was added drop by drop. The observation was noted.
3. Step 1 to 2 was repeated with butylamine.
4. A spatula- measure of ammonia chloride in about 3cm3 of water was dissolved. Then
bromine water was added as before. The observation was noted.
Results:
Phenylamine Butylamine Ammonia
1(a) Solubility in water soluble soluble soluble

1(b) pH value in water 6 11 9

2.Reaction with aq.HCl Turn white cloud White fume into White fume into
into brown liqiud liquid colorless liquid colorless
3.Reaction with CuSO4 Turn light Blue into Turn light blue into Light blue into
green dark blue dark blue

4. Reaction with bromine water Orange brown into No reaction No reaction

decolorized
Ammonia chloride White precipitate

Discussions:
Phenylamine reacts reversibly with water to give phenylammonium ions and hydroxide ions,the
chemical equations: .

Phenylamine is a much weaker base than ammonia and butylamine

The carbon chain in a butylamine molecule is terminated by an amine group, which has dipoles.
The nitrogen atom has a partial negative charge due to its electronegativity being much higher
than the hydrogen atoms it is bonded to.Butylamine can dissolve in water by forming hydrogen
bonds with water. Oxygen atoms in water hydrogen-bond to hydrogen atoms on the amine
group. The nitrogen atom in the amine group hydrogen-bonds to hydrogen atoms in water
molecules.
Phenylamine reacts with hydrochloric acid and a very weak base, with a strong acid. This because
the attractiveness of the lone pair is lessened because of the way it interacts with the ring
electrons.
The butylamine will react with hydrogen chloride in the gas state to produce white smoke as
ammonia.
CH3CH2CH2CH2NH2(g) + HCl(g) CH3CH2CH2CH2NH3+ (s) + Cl-(s)

Ammonia reacts with acids to produce ammonium ions and the ammonia molecule picks up a
hydrogen ion from the acid and attaches it to the lone pair on the nitrogen.

Ammonia acts as a Bronsted-Lowry base. The hydrogen ions are pulled off two water molecules
in the hexaaqua ion.This produces a neutral complex which one carrying no charge.The lack of
charge cause the neutral complex isn't soluble in water, and hence produce a pale blue
precipitate.

This precipitate is called copper(II) hydroxide. The reaction is reversible because ammonia is
only a weak base.That precipitate dissolves when add an excess of ammonia solution, produce
deep blue solution. The ammonia replaces four of the water molecules around the copper to give
tetraamminediaquacopper(II) ions.

The same reactions apply for butlyamine and phenylamine with copper(II) sulphate.
When bromine water is added to phenylamine, the bromine water is decolourised and a white
precipitate is formed. The -NH2 group attached to the benzene ring in phenylamine has the effect
of making the ring much more reactive The lone pair on the nitrogen touches the delocalised ring
electrons and becomes delocalised with them.

Butylamine and ammonia no reaction for bromine water.

Questions:
1. Butylamine and phenyamine stronger base than ammonia . this due to present of ring in
phenylamine and alkyl group in butylamine.
2. All amines are soluble in water and react with hydrochloric acid.
3. The reaction with aqueous bromine (Bromine water, Br2) .It produce 2,4,6-
tribromophenylamine which seen as white precipitate and the colour of bromine colour
will be decolourized.
Conculsions:
Phenylamine not slouble in water but butylkamine and ammonia are soluble in water.
Phenylamine ,butylamine and ammonia react with aqeous hydrochloric acid and copper(II)
sulphate. Only phenylamine reaction with bromine water.

References:
1. INTRODUCING AMINES [online]. Available at:
https://www.chemguide.co.uk/organicprops/amines/background.html#top accessed
[23 December 2017].
2. AMINES AS BASES [online]. Available at:
https://www.chemguide.co.uk/organicprops/amines/base.html#top [23 December
2017].
3. AMINES AS BASES [online]. Available at:
https://www.chemguide.co.uk/organicprops/amines/base.html#top [23 December
2017].
4. PHENYLAMINE (ANILINE) [online]. Available at:
https://www.chemguide.co.uk/organicprops/anilinemenu.html#top [23 December
2017].