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03
Objective:
Apparatus:
Chemicals used:
i. Benzene
ii. Sulfuric acid
iii. Nitric acid
iv. Water
Principle:
Benzene - is an important organic chemical compound with the chemical formula C6H6 The
benzene molecule is composed of 6 carbon atoms joined in a ring with 1 hydrogen atom attached
to each. Because it contains only carbon and hydrogen atoms, benzene is classed as
a hydrocarbon. Benzene is a natural constituent of crude oil and is one of the
elementary petrochemicals. Because of the cyclic continuous pi bond between the carbon atoms,
benzene is classed as an aromatic hydrocarbon. It is a colorless and highly flammable liquid with
a sweet smell. It is used primarily as a precursor to the manufacture of chemicals.
Nitration - is a general class of chemical process for the introduction of a nitro group into an
organic chemical compound. The process involves a nitrating agent mostly nitric acid HNO3 or
NO2.
The electrophile (nitronium ion NO2+) can be generated by the following reaction of the mixture
of acids:
The electrophile then attack on nucleophilic benzene ring to substitute hydrogen giving off nitrobenzene
as follows:
This nitration reaction is highly exothermic. The temperature should not exceeds 50oC and is
maintained in between 50oC & 60oC as the nitration process is highly dependent on the
temperature and hence influencing the extent of nitration which ultimately determines the
number of nitro groups attached to the benzene ring.
Moreover, special care should be taken while preparing the mixture of acid as great amount of
heat is released as nitric acid contains water and hence due to the hydration of the proton
released by the sulfuric acid. i.e.
Also benzene is also smoothly and very slowly added in the acid mixture in order to avoid rise in
temperature due to exothermic nature of the reaction. Ice bath must be used during the addition.
The reaction mixture must be heated for 40 to 45 minutes in order to increase the yield.
Mechanism of reaction:
Step 1:
Step 2:
Step 3:
The above intermediate is sigma complex (arenium ion) and is resonance stabilized.
Step 4:
Nitrobenzene is a greenish-yellow crystalline solid or colorless to pale yellow, oily liquid with an
almond oil odor. Nitrobenzene is soluble in about 500 parts water and freely soluble in alcohol,
benzene, ether, acetone, and oils. It is also combustible with steam. It is very important
component of the explosives. Nitrobenzene exists in the atmosphere in the gas phase. The
dominant chemical loss process for nitrobenzene in the troposphere is expected to be by reaction
with the hydroxyl (OH) radical, although photolysis may be important. The calculated half-life
and lifetime of nitrobenzene due to reaction with the OH radical are 2 months and 3 months,
respectively.
Applications:
Procedure:
Precautions:
And hence,
Actual yield = 8 ml
= 8 / 33.185 x 100
= 24.107 %
Results:
Nitrobenzene is prepared in the laboratory and the % yield was found to be 24.107 %.