PHC 464

PHARMACEUTICAL ORGANIC CHEMISTRY

PRACTICAL 1:

MONONITRATION OF TOLUENE

LECTURER: DR SADIA SULTAN

DATE: 14/4/2022

PREPARED BY:

NAME STUDENT ID GROUP

24
24
24
24
BACKGROUND

The purpose of conducting this experiment is to have a greater understanding of

monosubstitution of toluene and its principle of electrophilic aromatic substitution.

Benzene is the simplest member of the aromatic chemical family, which includes
hydrocarbons with a molecular formula of C6H6 and three conjugated double bonds.
Monosubstituted derivatives are benzene derivatives with only one substituent, such as toluene.
Toluene is made up of two groups: a methyl group and a phenyl group. Because of the methyl
group, toluene shows electrophilic aromatic substitution and has a larger capacity for releasing
electrons than hydrogen atoms in the same place.

CALCULATIONS

Percentage yield of the product

Mol of toluene 3 ml x 0.87 g / 1 ml x 1 mol / 92.14 g = 0.02833 mol

Mol of nitric acid 8 ml x 1.42 g / 1 mol x 1 mol / 63.01 g = 0.1803 mol

Mass of dinitrotoluene 0.02833 mol x 1 mol (dinitrotoluene) / 1 mol (toluene) x 137.14 g / 1 mol
= 3.885 g

Percentage yield Actual yield / Theoretical yield x 100%

3.913 g / 3.885 g x 100%
= 100.72 %

DISCUSSIONS

Mononitration of toluene is the reaction of electrophilic aromatic substitution. Generally, it

involves the replacement of a hydrogen atom which is attached to a benzene ring with an
electrophile.

In this experiment, sulphuric acid is used to activate the nitric acid and produce nitronium
ion, which is a strong electrophile. At the beginning, ortho and para isomer are obtained as
product after toluene undergoing nitration as the methyl group is an activating group. A low
temperature is required so only one nitro group is substituted into the toluene. Swirling the flask
gently under running tap water or in ice bath is a very crucial precaution step.
 Then, the filtration was performed to collect the crude crystal by using the vacuum filtration.A
small amount of methanol was added for recrystallization to purify the crude crystal. The
purification step was performed to get only one major product as there may be other different
products in it.

Based on the experiment, the percentage yield that we have obtained is 100.72% which
is higher than 100%. The product might contain more solvents due to not completely dry when
the weighing of the product is done. Therefore, the purification step need to be carried out more
carefully in order to obtain a pure product.

CONCLUSIONS

As a conclusion, mononitration of toluene produces dinitrotoluene which is known as a

precursor to trinitrotoluene. The percent yield of this pale yellow crystalline solid is 100.72%
which is approximately 100%. This means that the product consists of a small amount of
impurities.
 PHC 464
PHARMACEUTICAL ORGANIC CHEMISTRY
PRACTICAL 2:

ESTERIFICATION

LECTURER: DR NURUL IZZATI BINTI OSMAN

DATE: 28/4/2022

PREPARED BY:

NAME STUDENT ID GROUP

1. DINIE NAJIHAH BINTI SUHAIMI 2021816996 PH2402A7
2. LISRANIA BINTI MOHD AMIN 2021887926 PH2402A7
3. NURUL AQILAH BINTI MOHD KAMAL 2021451364 PH2402A7
4. WAN KHAIRINA BINTI WAN KAMARULISHAM 2021613002 PH2402A7
BACKGROUNDS

This experiment is carried out to achieve the objective of learning the synthesis technique of
esterification as well as distillation technique in order to obtain an ester.

Ester is a product obtained by the reaction of carboxylic acid and alcohol with the presence of
an acid catalyst which is concentrated sulphuric acid. In order to shift the reaction equlibrium to
the right, the acid or alcohol needs to be used in excess. The pathway for the reaction involves
initial protonation of the carboxyl group, attack by nucleophilic hydroxyl, a proton transfer and
further with the loss of water followed by the loss of the catalysing proton to produce the ester.
All these steps are reversible, hence also the process.

CALCULATIONS

1)Yield of reaction:

Density of isoamyl alcohol Density of glacial acetic acid

= 0.890 g/ml = 1.05 g/cm3
Volume of isoamyl alcohol Volume of glacial acetic acid
= (5g/0.809 g/mL) = (6g/1.05 g/mL)
=6.2 mL = 5.7 mL

Number of moles of isoamyl alcohol Number of moles of glacial acetic acid

= 0.062 mol = 0.1 mol

Ratio: 1 mol of C5H12O = 1 mol of C7H14O2

0.062 mol of C5H12O = 0.062 mol of C7H14O2

Theoretical mass: 0.062 mol x 130g/mol = 8.06g

Actual mass: 4.97 g

Percentage yield: (4.97g/8.06g) x 100% = 61.66%

DISCUSSIONS:

Esters are compounds that are synthesized by the reaction of an oxoacid with a hydroxyl
compound such as alcohol or phenol. Esters are commonly obtained from an inorganic or
organic acid where hydroxyl group (-OH) is replaced with an alkoxy group (-O-alkyl) group. For
example, alcohol and carboxylic acids. Water is released during the reaction produced by
hydrogen from alcohol and hydroxyl group from acid. The formation of ester produces a
banana-flavored smell of fragrance.

During the experiment, the required compounds such as isoamyl alcohol, glacial acetic acid,
and concentrated sulphuric acid are added and mixed. Boiling chips are added to ensure the
boiling process is smoothly handled and prevent it from being bumped and superheated.The
mixture is condensed and filtered. Lastly, the final product which is the ester is weighed and
recorded.

Based on the experiment, the percentage yield obtained is 61.66% which is a bit low. The
low percentage yield can be due to the loss of product during the experiment such as pouring
and filtration. Moreover, it may be caused by the incomplete reactions in which some reactions
may not fully react to form the product. This can be overcome by applying the techniques
cautiously and meticulously. We should also carefully keep the temperature of the reaction and
liquid reagent at the correct level during addition and reaction and always stir the solution
continuously.

CONCLUSIONS

In conclusion, the objective of this experiment is achieved as our product is isoamyl acetate.
Isoamyl acetate which has a strong smell like banana is obtained from the esterification of
isoamyl alcohol and acetic acid. During the experiment, distillation also applied to separate
compounds with large differences in boiling points.