EXPERIMENT 4

REACTION OF AMINES

INTRODUCTION

Amines are aliphatic and aromatic derivatives of ammonia. Amines, like ammonia, are weak bases (K b
= 10 to 10 ). This basicity is due to the unshared electron pair on the nitrogen atom.

Amines are classified as primary, secondary, or tertiary based upon the number of carbon-containing
groups that are attached to the nitrogen atom. Those amine compounds that have only one group
attached to the nitrogen atom are primary, while those with two or three groups attached to the
nitrogen atom are secondary and tertiary, respectively.

OBJECTIVE
To -aminobutane and phenylamine)

APPARATUS

Test tube, blue and red litmus paper, hot plate and beaker (100 and 250 mL).

CHEMICALS
Aminobutane (butylamine), Phenylamine (aniline), acetic acid, acetic anhydride, dilute NaOH, Dilute
HCl, Phenolpthalein indicator, Bromothymol blue indicator and Benzoyl chloride.

PROCEDURE

a) Acidity, basicity and pH

1. Prepare two test tubes. Put 0.5 mL of aniline into each of the test tube with 1 mL of distilled
water.
2. Add two drops of phenolphthalein indicator into the first test tube and two drops of
bromothymol blue indicator into a second test tube.
3. Repeat the test (1) above on aminobutane using bromothymol blue indicator.
Note:
For experiment 1 and 2 use the following guide for bromothymol blue.
pH < 6 yellow
pH = 7 green
pH > 7.5 blue

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b) Solubility, reaction with HCl and NaOH

i. Add 3 mL of dilute HCl to 1 mL of aniline in a test tube and observe the solubility of aniline in
dilute HCl (compare its solubility in water).
ii. For comparing purpose: prepare another test tube with aniline but replace the HCl with H2O for
comparison.
iii. Add dilute NaOH a bit at a time to the solution in b(i) until it is alkaline to litmus paper.
Explain your observations together with the correct equations.

c) Reaction with acetic acid and acid anhydride

i. Dissolve 1 mL of aniline with 3 mL of acetic acid in a dry test tube and then add in 2 mL of
acetic anhydride. Shake the mixture vigorously. Pour in the mixture into a beaker containing 20
mL of cold water. Name the product.

d) Reaction with bromine water or aqueous bromine

i. Dissolve 1 mL of aniline in 2 mL of water in a test tube. Add in bromine water drop by drop and
shake the test tube after each addition of the bromine water. Keep on adding until there is a
physical change.

e) Reaction with NaOH and benzoyl chloride

i. In a test tube add in 1 mL of aniline and then 5 mL of NaOH. Shake th mixture hard about a
minute. After that, add 1 mL of benzoyl chloride. Put a stopper on the test tube and shake ir hard
for about 2 minutes. Let it stand for about half an hour. Observe any changes. (Note: of there is
still no physical change, put in a hot water bath).

DISCUSSION
In your discussion, you need to include equations of each reaction in the experiment above. State your
observation and give the conclusion of your results. If the observation does not comply with your
expectation, you need to give the reason and expected results of the experiment. Answer each question
given in the procedure above. Write discussion in proper arrangement.

QUESTIONS
1. Explain the following observations.
a) Aniline is more soluble in aqueous acid solution than in water.
b) A white precipitate is formed when aqueous bromine is added to aniline.
2. Using a suitable chemical test, differentiate the following pairs:
a) Aniline and ethanamine
b) Butanamine and N,N-dimethylethanamine
c) N,N-diethylaniline and aniline

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 DATASHEET EXPERIMENT 4
REACTION OF AMINES

Name:________________________________________ Date of Experiment: _______________

Student ID: ______________________________________________Group: _______________

Group Members:_________________________________________

Experiment Observations, equations and conclusions

a) Acidity, basic and pH

i. aniline and distilled water

ii.a) aniline and phenolphthalein indicator

b) aniline and bromothymol blue indicator

iii. aminobutane using bromothymol blue

indicator
Note:
For experiment 1 and 2 use the following guide
for bromothymol blue.

pH < 6 yellow
pH = 7 green
pH > 7.5 blue

b) Solubility, reaction with HCl and NaOH

i. aniline and HCl

ii. aniline and water

iii. addition of NaOH to the solution in B (i)

c) Reaction with acetic acid and acid anhydride

d) Reaction with bromine water or aqueous

bromine

e) Reaction with NaOH and benzoyl chloride

L ____________________________________

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