Benzene Nitration

Purpose

The aim of the experiment is the synthesizing of 1-methyl -4-nitrobenzene through an

electrophilic aromatic reaction. The reaction was achieved through the reaction of sulfuric nitric

acid with methylbenzene, and also the reaction of the same acids with benzaldehyde.

Additionally, the experiment aimed to look at the regioselectivity of the compounds involved.

Procedure

The procedure involved was the identification of the correct starting materials needed to

synthesize the target compound, in this case, 1 methyl -4-nitro-benzene, and adding the materials

in a round-bottomed flask. After the first step, the appropriate solvent was selected, and the

flasks were dragged to the stir plate. The correct reagent was also selected to help in the

synthesis process. After the process, the heater, condenser, and nitrogen gas were attached to the

round-bottomed flask to heat the moisture. After the reaction was completed, a funnel extraction

process was done with the layer inside the flask containing multiple compounds to separate the

mixture, and a distillation process was performed through stirring. The temperature of the

reaction was monitored through a thermometer. As the temperature increased, the products

evaporated and distilled in the collection flask at the back of the apparatus, depending on the

boiling points. The products that were not needed were discarded until the desired product was

isolated.

Data and Results

In the first plate, after the nitration of methylbenzene, a single solution was formed. At

the end of the reaction, 1 methyl-2.4-dinitrobenzene remained in the flask. The intermediate step

contained 1-methyl -2 nitrobenzene and I methyl-4 nitro-benzene, but since they were not found
in the end product, there was no need to include them. During the reaction, there are three major

possibilities for placement where the nitro group can be placed as meta, para, or ortho. A nitro

group can be described as a deactivating group because it removes electron density. Nitration of

benzaldehyde in the aldehyde group is a meta-directing group. An ortho-substituted result is the

main result because the compound formed is stable. A mono-substituted nitro-benzene contains

lower activation energy because the reaction is quicker. According to the reaction, the aldehyde

directs the incoming nitronium towards the meta position. Benzaldehyde is the deactivating

group because it takes electron density from the benzene ring. Generally, the reaction of

benzaldehyde with nitro/sulfuric acid produced 3- 3-nitro benzaldehyde.

Discussion

The nitration of benzene is an aromatic electrophilic reaction. During the process,

benzene reacted with concentrated nitric acid in the presence of sulfuric acid to produce

nitrobenzene. The first step involved the nitric acid accepting a proton from the sulfuric acid and

then dissociating to form a nitronium ion. The second step is nitronium ion acting as an

electrophile in a process that further reacts with benzene to form an arenium ion. The last step is

where the arenium ion loses the proton to form a Lewis structure, with the base being a

nitrobenzene.

Conclusion

In summary, nitration of methylbenzene leads to formation of 1-mtehyl -2 nitrobenzene.

If the reaction continues for several hours, it will lead to the formation of 1-methyl-2-4

dinitrobenzene. The results are easy to obtain because the reactants have lower activation energy.
The reaction can be described as meta-directing because the aldehyde uses the benzene ring and

electric ring in the nitration process. The values obtained from NMR and FTIR spectra confirm

the synthesis of 1-methyl-4 nitrobenzene.