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EXPERIMENT 6 : REACTIONS OF AMINES

NAME
NO. MATRIX
GROUP
LAB
PARTNERS
LECTURER
NAME
DATE OF
EXPERIMENT
DATE OF
SUBMISSION

PRE LAB ASSIGNMENT


1) Write a two paragraphs theory about amines.
Amines are an organic compounds containing one or more nitrogen atoms. Structurally
amines can be same as ammonia, however amines have additional properties based on
carbon connectivity. In amine, one or more hydrogen attached to nitrogen can be
replaced either alkyl or aryl group. Amines can be primary, secondary and tertiary
based on number of alkyl group that attached to the amines. Organic compound which
have multiple amine group are called diamine, triamine and so forth. When amine
become a substituent, they are called amino.

Amines are basic, so they can neutralize acids to form salts and water. When amines
react with carbonyl compounds, they produce imines and when amines react with
aldehydes, they form aldimines and with ketones become ketimines. In case for
formaldehyde, imine products are cyclic trimmers.

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 AND RESULTS


Experiment
Observations:
1)
Two test tubes containing 0.5ml of Aniline

aniline in each was prepared. Then, Phenolphthalein: Two layer form (top : oily brown and
1ml of distilled water was added in bottom : clear solution)
each of the test tube. Two drops ofExpected:
phenolphthalein was added into the Aniline is a weak base, the colour produced supposed to
be pink to fuchsia.
first test tube and 2 drops of
bromothymol blue into the second test
Bromothymol blue: Two layer form (top : light blue clear
tube. The test was repeated by using 1-
solution and bottom : oily brown
aminobutane. The observations was
1-aminobutane
explained based on the colour change
for bromothymol blue indicator at Phenolphthalein: Clear pink solution

different pH as follows: Bromothymol blue: Clear dark blue solution (pH> 7.5)
Conclusions/ explanations:
pH< 6 yellow
pH=7 green Aniline
pH>7.5 blue Phenolphthalein: Aniline is a weak base. The obtained is
different from expected may be caused by the impurities
that are present in the bottom of the test tube.
Bromthymol blue: Aniline is a weak base. The blue colour
of the aniline produced shows that it has a pH around > 7.5
that is weak basic.
1-aminobutane
Phenolphthalein: 1-aminobutane is base
Bromothymol blue: 1-aminobutane is weak base

2) Observations:
3ml of dilute HCl(aq) was added to a) Dilute HCl: Soluble
1ml of phenylamine in a test tube. Distilled water: Slightly soluble in water and forming
oily brown particles
3ml of distilled water was added to
1ml of phenylamine in another test b) Brown colour changed to cloudy and tiny oil drop
formed
tube. The solubility of phenylamine Equations:
in dilute HCl(aq) was observed as i) C6H5NH2 + HCl → C6H5NH3+Cl-
compared to its solubility in water.
ii) C6H5NH2 + H2O → C6H5NH3+ + OH-
In the test tube containing HCl(aq) Conclusion:
and phenylamine, the dilute Due to the presence of lone pair of electrons on the nitrogen
NaOH(aq) was added little bit at a atom, phenylamine is a basic compound, hence it reacts
time to the solution in until it is with hydrochloric acid to form phenyl ammonium chloride
alkaline to red litmus paper. and becomes soluble in HCl. Then it is slightly soluble in
distilled water and the solution is known as aqueous aniline.
When the dilute NaOH was added, a solution of white
emulsion formed which is phenyl ammonium chloride.
3) Observations:
1ml of phenylamine was dissolved
Brown homogenous solution was produced and it is soluble
with 3ml of acetic acid in a dry test
in HCl.
tube. 2ml acetic anhydride was Equations:
added and the reactant mixture was C6H5NH2 + CH3COOH  CH3CONHC6H5 + H2O
shaken vigorously. The mixture C6H5NH2 + (CH3CO)2O  CH3CONHC6H5 + CH3COOH
was then poured into 20ml ice-cold Name the products:
water in a beaker N-phenylethanamide

4) Observation:
0.5ml of phenylamine was added in
Initial stage addition of bromine water:
0.5ml of water in a test tube. 0.5ml
Clear solution with oil layer changed to cloudy solution and
bromine water was added and the
oil layer.
test tube was shaken. The addition
Excess addition of bromine water:
of 0.5ml of bromine water was
Phenylamine soluble and yellowish
repeated until there is a physical
change occur. The observations was
Expected : Clear solution turns cloudy with white
explained and an equation for the
precipitate formed
reaction was written Equations:
C6H5NH2 + H2O  C6H5NH3+ + OH-
Conclusion: (NAME OF MAIN PRODUCT)
Phenylamine is aromatic amine as the brown colour
bromine water decolourised. However, when excess of
bromine water was added, white precipitate formed. This is
because phenylamine has completely reacted with bromine
which the product known as 2,4,6-tribromophenylamine
5) Observations:
5ml of dilute NaOH(aq) was added
a) Heterogeneous solution was produced. Reddish orange
to 1ml of phenylamine in test tube,
solution on top and colourless solution on the bottom.
and then the tube was vigorously
shaken for one minute. For the
b) Heterogeneous solution was produced. Red solution on
second test tube, 1 ml of benzyl
top and cloudy solution on the bottom.
chloride was added, and the mouth Equations:
+ +
of the test tube was covered with a a) C6H5NH3 + NaOH → C6H5NH2 + H2O + Na
stopper. The tube was then b) C6H5NH2 + C6H5COCl + NaOH → C6H5NHCOC6H5 +
vigorously shaken for two minutes. NaCl + H2O
Conclusion:
The mixture was cooled down. N-Phenylbenzamide are formed.

QUESTION
1) What make amines weak bases and able to form salts with mineral acids?
Unshared electron pair of the nitrogen atom can be form a coordinate bond with
proton. It actually reacts 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.

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