Experiment 6: Reaction of Amines

Chemicals:

Butylamine
Aniline
Ethanoic acid
Acetic acid anhydride
Dilute NaOH
Dilute HCL
Phenolphthalein indicator
Bromothymol blue indicator
Benzoyl chloride

Apparatus :

5-10 test tube

250 mL beaker
100 mL beaker
Blue and red litmus paper
Hot plate

Procedure:
(1)
1. Two test tubes were prepared which contained 0.5 mL of aniline in each.
Then, 1 mL of distilled water was added in each of the test tube.
2. Two drops of phenolphthalein was added into the first test tube and 2 drops
of bromothymol blue was added into the second tube.
3. The test was repeated using 1-aminobutane

(2)
1. 3 mL of diluted HCl was added to 1 mL of phenylamine in a test tube. In
another test tube, 3 mL of distilled water was added to 1 mL of
phenylamine. The solubility of phenylamine in dilute HCl was observed as
compared to solubility in water.
2. In the test tube containing HCl and phenylamine, diluted NaOH was added
little bit at a timeto the solution until it was alkaline to red litmus paper.

(3)
1. 1 mL of phenylamine was dissolved with 3 mL of acetic acid in a dried test
tube. 2 mL acetic anhydride was added and the reactant mixture was
shaken vigorously.
2. The mixture was poured into 20 mL ice-cold water in a beaker.

(4)
1. 0.5 mL of phenylamine was dissolved in 0.5 mL water in a test tube. 0.5
mL bromine water was added and the test tube was shaken. The addition
of 0.5 mL bromine water was repeated until there was physical change
occurs.

(5)
1. 5 mL of diluted NaOH was added to 1 mL of phenylamine and the tube
was shaken vigorously for a minute.
2. 1 mL benzoyl chloride was added; the mouth of the test tube was covered
with rubber stopper and vigorously shaken for two minutes. The mixture
was cooled down

Result:

Conclusion :
1. Reaction with phenolphthalein and bromothymol blue
- 1 aminobutane- color changes to margenta (base/alkali) -phenolphthalein
indicator
- Remain blue in color ( base) bromothymol blue

Aniline color changes to yellow -phenolphthalein

- Remain blue (base) bromothymol blue

2. Solubility of phenylamine in dilute HCL and effect of adding the

dilute NaOH
- Slightly soluble in water
- Dissolve free in dilute HCL
- A solution of salt formed-phenyl ammonium chloride

3. Reaction of phenylamine with acetic anhydride in the precense of

acetic acid
- Crystal formed
- Brown color changes to brighter color

4. Reaction of aniline with bromine water

- Bromine water decolourised
- White precipitate formed
- Precipitate = 2,4,6-tribrophenylamine
5. Reaction of phenylamine in NaOH (aq) with Benzoyl chloride
-ester is produced with the presence of benzoyl chloride

Question
1. What make amines weak base and able to form salts with mineral acids ?
- Unshaired electron pair of the nitrogen atom can form a coordinate bond
with proton. it actually react with the mineral acid to form an amine salt. A
water insoluble amine can be made to dissolve by adding acids to form its
water soluble amine salt.