PHC 464 Pharmaceutical Organic Chemistry

Faculty of Pharmacy
Universiti Teknologi MARA

Title of Practical
Lab 1: Mononitration of Toluene and Lab 2: Esterification

Session
14th April 2022 and 28th April 2022

Preceptor
Prof. Sadia Sultan

Name Student ID Group

Background. Calculation
Aromatic organic compounds such as toluene can 𝐶7𝐻8(𝑙) + 𝐻𝑁𝑂3(𝑙) → 𝐶6𝐻4(𝐶𝐻3)(𝑁𝑂2) (𝑙) + 𝐻2𝑂(𝑙)
undergo mononitration at the ortho or para position Limiting reactant: 𝐶7𝐻8
via electrophilic substitution reaction without
Mass of toluene
heating.This is due to the fact that methyl group 𝑚
𝑑 = 𝑣
which is the substituent at the benzene ring is
activating group. This mechanism involves the 𝑚 = 𝑑 × 𝑣 = 0. 87 × 3 = 2. 31𝑔
2.31𝑔
attack of nucleophile species (benzene) towards the No. of mol: 92.14𝑔//𝑚𝑜𝑙 = 0. 025𝑚𝑜𝑙
electrophile species which is the nitronium ion. The Excessive reactant: 𝐻𝑁𝑂3
nitronium ion originated from the nitrate acid which Mass of nitric acid
is one of the reactants used in the reaction. 𝑚
𝑑 = 𝑣
However, if nitration of toluene is done under the
existence of heat, it will result in formation of 𝑚 = 𝑑 × 𝑣 = 1. 51 × 8 = 12. 08𝑔
12.08𝑔
dinitrotoluene and ultimately become a No. of mol: 63.01𝑔//𝑚𝑜𝑙 = 0. 192𝑚𝑜𝑙
trinitrotoluene. Theoretical yield
1 𝑚𝑜𝑙 𝑜𝑓𝐶7𝐻8
= 2. 31𝑔 𝐶7𝐻8 × 92.14 𝑔
✕
Discussion. 1 𝑚𝑜𝑙 𝑜𝑓𝐶6𝐻4(𝐶𝐻3)(𝑁𝑂2) 137.14𝑔
×
Electrophilic substitution reaction of toluene began 1 𝑚𝑜𝑙 𝑜𝑓𝐶7𝐻8 1 𝑚𝑜𝑙 𝑜𝑓𝐶6𝐻4(𝐶𝐻3)(𝑁𝑂2)

with protonation of nitric acid by sulphuric acid to = 3. 44 𝑔

produce a nitronium ion. Sulphuric acid also acted
as a catalyst to speed up the reaction. The
nitronium ions acted as an electrophile which was
then attacked by a benzene ring. Since toluene
consists of methyl group (an activating group), it has
directed the substitution of electrophile towards
ortho and para position. This was because the
activating group has increased the electron density
at ortho and para position by resonance.
As the methyl group was not bulky, the major
product of mononitration of toluene was
ortho-nitrotoluene rather than para-nitrotoluene.
In this experiment, we conducted recrystallization on
the product to remove impurities that might exist.
The actual yield was 1.512 g while the theoretical
yield should be 3.440 g. Based on this result, the
percentage yield for the recrystallization obtained
was 44%. The final product may contain remaining
impurities due to the improper handling during
filtration of crystal.
Actual yield of 𝐶6𝐻4(𝐶𝐻3)(𝑁𝑂2)
Filter paper = 0. 60 𝑔
Filter paper + product = 2. 11 𝑔
2. 11𝑔 − 0. 60𝑔 = 1. 51𝑔
1.51
Percentage yield = 3.44 × 100% = 43. 89%
Conclusion.
In conclusion, mononitration of toluene could be obtained by
electrophilic substitution. The reaction did not require heat in
order to get the mono substitution of toluene. The final product
needed to be recrystallized to get the pure product as it has
impurities. The existence of impurities may occur because of
the incomplete reaction between reactants, some parallax
error, and product losses during the transferring process.

Mechanism:
 Title of Practical
Lab 2: Esterification

Background. Calculation.
Isoamyl acetate has been derived from the reaction between 𝐶𝐻3𝐶𝑂𝑂𝐻 (𝑙) + 𝐶5𝐻12𝑂 (𝑙) = 𝐶7𝐻14𝑂2(𝑙) + 𝐻2𝑂(𝑙)
isoamyl alcohol and acetic acid through the reaction called
esterification in presence of catalyst such as concentrated Limiting reactant: 𝐶5𝐻12𝑂 (isoamyl alcohol, 5 g)
sulphuric acid. Esters are distinct in that they generally emit a 5𝑔
No. of mol: = 0. 056𝑚𝑜𝑙
strong, pleasant odor. Therefore they are commonly used as 88.15𝑔/𝑚𝑜𝑙
fragrance and essential oil. This reaction also produces water Excess reactant: 𝐶𝐻3𝐶𝑂𝑂𝐻 (acetic acid, 6 g)
from hydroxyl ion from the acetic acid and hydrogen ion from No. of mol:
6𝑔
= 0. 099𝑚𝑜𝑙
60.05𝑔/𝑚𝑜𝑙
isoamyl alcohol that then can be used to synthesize ester.
Through this experiment, the distillation process involved in Theoretical yield:
collecting isoamyl alcohol to extract out alcohol or water 1 𝑚𝑜𝑙 𝑜𝑓 𝐶5𝐻12𝑂 1 𝑚𝑜𝑙 𝑜𝑓𝐶7𝐻14𝑂2 130.19 𝑔 𝐶7𝐻14𝑂2
present. 5𝑔 𝐶5𝐻12𝑂 × 88.148 𝑔
× 1 𝑚𝑜𝑙 𝑜𝑓 𝐶5𝐻12𝑂
× 1 𝑚𝑜𝑙 𝑜𝑓𝐶7𝐻14𝑂2
= 7.385 g

Actual yield: 0. 586 𝑔

0.586𝑔
Percentage yield: 7.385𝑔 × 100% = 7. 935%

Discussion. Conclusion.
The esterification process began with the isoamyl alcohol In conclusion,we are able to understand the synthesis
reacting with acetic acid in the presence of concentrated and distillation technique in the formation of ester,
sulphuric acid as a catalyst to produce an isoamyl acetate and isoamyl acetate. From the experiment the data
water. Acetic acid is a carboxylic acid with a chemical formula collected enabled the determination of the percentage
CH3COOH and functional group –COOH while isoamyl alcohol yield of isoamyl acetate. We can conclude that some
is an alcohol with a chemical formula C5H12O and functional errors might occur during the experiment because the
group –OH. In the reaction, we included boiling chips to avoid low percentage yields 7.935% , which is less than
overheating and provide a mixing effect. When this reaction 100%. Thus, the accuracy of the result is reduced.
occurs, protonation of carbonyl oxygen by sulphuric acid,
𝐻2𝑆𝑂4 was first took place. This has caused the carbonyl atom
in acetic acid to become more electrophile thus it was more
favorable to be attacked by nucleophile species (isoamyl
alcohol) during the next step. After dehydration as well as
deprotonation on carbonyl oxygen, an ester, isoamyl acetate or
also known as isopentyl acetate, C7H14O2 will become a
product and water will form as a side product.

The percentage yield of the ester is 7.935%. We got a low yield

because of some errors that might occur during the experiment
which resulted in low production of the product. We should
provide sufficient catalysts and ensure the mixture was
completely heated to obtain a complete reaction between
isoamyl alcohol and acetic acid. Plus, some reactants and
products might lose during transferring and weighing,
decreasing the amount that reacts. We should practice the right
techniques in handling the apparatus and ingredients.The
presence of a water bath also contributes to the separation of
the ester. The acids and alcohol dissolve in water, forming a
thin layer in the beaker where the ester is contained. Thus, we
can obtain the pure ester at the end of the process.

Isoamyl acetate is a fruity-smelling ester that also can be

naturally formed by ripening fruit. It gives out a strong, fruity
banana or pear odor that is commonly used to flavor dishes,
attract bees, and improve fragrance.

Esterification of Isoamyl Acetate Mechanism.