FACULTY OF APPLIED SCIENCE

LABORATORY REPORT
CHM413 (ORGANIC CHEMISTRY)
EXPERIMENT 6: REACTIONS OF AMINES

NAME: NURUL RABIATUL ADAWIYAH BT MASRI

STUDENT NUMBER: 2022899802

PARTNER’S NAME: 1) FARHAH BATRISYIA BINTI ABDUL RAHIM (2022899798)

2) DANIAL ALIFF NAJMY BIN MOHD ZAINIZI (2022868598)

LECTURER’S NAME: DR. NORAISHAH ABDULLAH

DATE OF EXPERIMENT: 9/5/2023

DATE OF SUBMISSION: 30/5/2023

JOTTER
Pre-lab assignments

1)Write a two paragraphs theory about amines.

Amines are organic substances that have a lone pair of nitrogen atoms in them. In
essence, they are produced by replacing one or more hydrogen atoms in ammonia (NH3) with
an alkyl or aryl group, giving them the names alkylamines and arylamines, respectively. The
following describes the amine functional group: The amount of hydrocarbon groups bonded to
the nitrogen atom determines whether an amino acid is primary, secondary, or tertiary. Primary
aromatic amines include aniline, whereas primary alkyl amines include methylamine and
amino acids. Two organic substituents, either alkyl or aryl, or both, are bonded to the nitrogen
along with one hydrogen in secondary amines.
Hence, amines are basic and readily react with the electron-poor hydrogen of acids, as
seen below. Because of the lone pair electrons on the nitrogen, amines are one of the few neutral
functional groups that are regarded as bases. The Hinsberg test is a chemical procedure that is
frequently used to identify primary, secondary, and tertiary amines. A Hinsberg reagent reacts
with an amine when there is an aqueous alkali present.

2) Draw the general structures for primary, secondary and tertiary amines.
CHEMICALS
1-aminobutane (buytlamine)
phenylamine (aniline/aminobenzene)
glacial acetic acid/ethanoic acid
acetic anhydride/ethanoic acid anhydride
dilute NaOH(aq)
dilute HCl(aq)
phenolphthalein indicator
bromothymol blue indicator
benzoyl chloride

APPARATUS
5-10 test tubes
One 250 ml beaker
Two 100 ml beaker
Blue and red litmus paper
Hot plate

PROCEDURE
1)
a) Two test tubes containing 0.5 ml of aniline in each were prepared. Then 1 ml of distilled
water was added in each of the test tube
b) Two drops of phenolphthalein was added into the first test tube and 2 drops of bromothymol
blue into the second test tube.
c) Test was repeated using 1-aminobtene.
d) The observations were explained based on the colour change for bromothymol blue indicator
at different pH as follows:
pH<6 yellow
pH=7 green
pH7.5 blue
2)
a) 3 ml of dilute HCl(aq) was added to 1 ml of phenylamine in attest tube. In another test tube,
3 ml of distilled water was added to 1 ml of phenylamine. Next, the solubility of phenylamine
was observed in dilute HCl(aq) as compared as to its solubility in water.
b) In test tube contained HCl(aq) and phenylamine, little bit of a dilute NaOH(aq) was added
in at a time to the solution until it was alkaline to red litmus paper.

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

4)
a) 0.5 ml of phenylamine was dissolved in 0.5 ml water in a test tube. 0.5 ml of bromine water
was added and the test tube was shaken. The addition of 0.5 ml of bromine water was repeated
until there was a physical change occurred. The observations were explained and the equation
for the reaction was written.

5)
a) 5 ml of dilute HCl(aq) was added to 1 ml of phenylamine in a test tube and the tube was
shaken vigorously for one minute.
b) 5 ml of dilute HCl(aq) was added to 1 ml of phenylamine in a test tube and the tube was
shaken vigorously for one minute. 1 ml of benzoyl chloride was added, the mouth of test tube
was covered with a rubber bung or stopper and the test tube was shaken vigorously for two
minutes. The mixture was let to cool down.
RESULTS
1)
Observations Aniline
Phenolphthalein: Two layer formed (top: colourless solution and
bottom: brown precipitate formed).

Expected: Aniline is a weak base, the colour produced supposed to be

pink to fuchsia.

Bromothymol blue: Two layer formed (top: green solution and bottom:
brown precipitate formed)

1-aminobutane
Phenolphthalein: Pink colour solution formed.

Bromothymol blue: Blue colour solution formed, (pH>7.5).

Conclusions Aniline
Phenolphthalein: The presence of the amine group in the solution is
shown by the dark pink colour of the solution. To determine whether an
amine group is present, phenolphthalein is utilised. Hence, a fragile base
is aniline. The results' discrepancy from expectations might be brought
on by impurities in the test tube's bottom.

Bromothymol blue: A fragile base is aniline. The generated aniline's

blue colour indicates that it has a weak basic pH of > 7.5.

1-aminobutane
Phenolphthalein: Despite the fact that 1-aminobutane is an alkane
molecule, it nevertheless contains an amine group in the amino form.
The amino group in the solution caused the solution to become pink
solution as a result.

Bromothymol blue: The blue solution stays the same since 1-

aminobutane doesn't contain a bromine ion. The colour of the solution,
which indicates that its pH is 7.5, indicates that it is basic.
2)
Observations a)When HCl was added, the solution was soluble; however, when water
was added, the solution was insoluble.

b)Then, after adding NaOH to the solution, the solution partly

dissolved. The solution split into two layers and become cloudy
solution.

Equations i. C6H5NH2 + HCl ⇌C6H5NH3 +Cl-

ii. C6H5NH2 + H2O ⇌C6H5NH3+ + OH-
Conclusions i.When the HCl was added, the solution takes on an acidic state, making
it soluble. On the other hand, the addition of water makes the solution
soluble since water has a weak base. Water therefore causes the solution
to become more basic than it was, making it insoluble.
ii.However, when more NaOH is added, the solution only becomes
partly a solution since the NaOH adds a little amount of a basic
condition to the solution.

3)
Observations Cloudy solution formed with white precipitate.
Equations i.C6H5 NH2 + CH3COOH→CH3CONH C6 H5 + H2O
ii. C6H5NH2 +(CH3CO)2O→CH3CONH C6H5 + CH3COOH
Name the product N-phenylethanamide

4)
Observations Initial stage addition of bromine water:
The bromine water was decolourised and cloudy solution formed.

Excess addition of bromine water:

Pale brown solution formed.
Expected: Clear solution turns cloudy with white precipitate formed.
Equations C6H5NH2 + H2O→ C6H5NH3+ + OH-
Conclusions To distinguish between an aromatic amine and an aliphatic amine, use
bromine water as a test. The brown colour of bromine fades when
bromine water is introduced to aromatic amine. In this experiment, the
bromine water's brown hue faded, demonstrating that phenylamine is an
aromatic amine. However, white precipitate was produced when too
much bromine water was added. This is due to the full reaction between
phenylamine and bromine, resulting in the compound known as 2,4,6-
tribromophenylamine.
5)
Observations a) Heterogeneous solution was produced. Two layers formed where
reddish orange solution on top and colourless solution on the bottom

b) Heterogeneous solution was produced. Two layers formed where red

solution on top and cloudy solution on the bottom.

Equations i. C6H5NH3+ + NaOH→ C6H5NH2 + H2O + Na+

ii. C6H5NH2 +C6H5COCl +NaOH → C6H5NH COC6H5 + NaCl + H2O
Conclusions N-phenylbenzamide is produced when phenylamine and benzoyl
chloride react. Thus, this experiment considered success.

ANSWERS
1.What make amines weak bases and able to form salts with mineral acids?
Amines can function as a weak base by becoming "proton acceptors" when they form bonds
with hydrogen ions. A molecule has to be able to react with acids, which are proton donors, in
order to function as a base. When an amine absorbs a proton from a hydrogen ion, conjugate
acids are created. Amines may also create conjugate acids. Hence, amines and strong acids ar e
combined to create amine salts. The NH3+ group can be found in primary amine salts, NH2+
in secondary amine salts, and NH+ in tertiary amine salts. Because they are utilised to make
medicinal compounds more water soluble and hence more accessible, amine salts are
significant.
REFERENCES
• amines as bases. (n.d.).

https://www.chemguide.co.uk/organicprops/amines/base.html

• Admin. (2021). Classification &amp; Nomenclature Of Amines | Preparation Of

Amines. BYJUS. https://byjus.com/chemistry/classification-of-amines/

• Grover, J. (2023). Classification of Amines: Primary, Secondary and Tertiary

Amines. Collegedunia. https://collegedunia.com/exams/classification-of-amines-

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