MONONITRATION OF

TOLUENE
PH2402C
Prepared by:
NUR SYAFIQAH BINTI IZZUDDIN
2015428442
RUZAINI FARHANA BINTI RUDZUAN
2015428912
PROCEDURE

1. 8 mL of concentrated nitric acid were measured and poured into 100 mL Erlenmeyer
flask.
2. Next, 8 mL of concentrated sulphuric acid were added slowly to the nitric acid and gently
swirled in cold water until it has cooled to room temperature. This step was conducted

carefully in the fume hood as the concentrated nitric and sulphuric acid can cause severe
burns.
3. After the acid has been mixed, 3 mL of toluene were added with a few drops at a time.
4. The mixture was kept at room temperature by swirling it in the ice bath.
5. Then, the mixture was swirled at room temperature for another 5 minutes after all the
toluene has been added. After 5 minutes, it was cooled in an ice bath.
6. Next, about 20g of chopped ice was added to the flask and the mixture was stirred with
scrapping. Solid lumps of the products was broke up and any excess ice was allowed to
melt. The solid collected by filtration was being wash with a little water.
7. Next, 2 mL of hot methanol was added in a test tube containing the solid to recrystallize
it.
8. After all of the solid had been dissolved, they are allowed to cool and chilled in an ice
bath.
9. The solid was then collected by another filtration and being left until it dry. The
recrystallized product were weighed.
RESULT

DISCUSSION
Electrophilic aromatic substitution is a very useful method for adding many different substituents
on a benzene ring. In this experiment, we will put (-N O2 ) group on a benzene ring which
already has a methyl (-C H 3 ) group in it which we called toluene. The methyl group facilitate

the nitration 25 times faster than benzene under identical condition. The nitronium ion (NO 2+)
formed from concentrated nitric acid and sulphuric acid is the actual electrophile in this reaction.
The sulphuric acid is regenerated and hence acts as a catalyst. It also absorbs water to drive the
reaction forward.

Figure 1

Formation of nitronium ion

Theoretically, the nitration of toluene generates a mixture of products. Thus, the major
products are the substituents at ortho and para position.

Figure 2 The products of nitration of toluene

The methyl group is an activating group, therefore ortho and para directing. The alkyl
groups donates electron density to the electron deficient carbon. This is called inductive
stabilization. The alkyl groups donate electron to the ring, stabilizing the carbocation. The
resonance effects are shown in the figure below.

Figure 3 Resonating structures of toluene

As toluene gives ortho and para nitrotoluene isomers, the temperature in the experiment
must be controlled because the heat produced in the reaction can give further reaction of
producing dinitrotoluene and ultimately the explosive trinitrotoluene (TNT). The precautions
steps such as swirl gently under running tap water or in an ice bath are important. After obtaining
the products, more soluble ortho isomer may be removed with proper washing. The crude
material may be purified by recrystallization from a small amount of hot methanol.
The percentage yield of our experiment is

. The explanation for this is that there is two

possible position in which nitro will be added. In the crude sample, several different products
may be detected, but after purification, only one major product remained. Furthermore, the more
soluble ortho isomer may have been removed during washing. Because some of the products
were washed away, a lower yield was observed.