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CHM457 Lab 5 PDF

The document describes an experiment to prepare methyl m-nitrobenzoate through an electrophilic aromatic substitution reaction. Methyl benzoate is reacted with nitric acid and sulfuric acid at low temperatures. This results in a nitro group replacing a proton on the aromatic ring to form methyl m-nitrobenzoate. The product is recrystallized and has a melting point close to the literature value of 78°C. The percentage yield is calculated to be 77.84%, close to the theoretical yield.

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4K views

CHM457 Lab 5 PDF

The document describes an experiment to prepare methyl m-nitrobenzoate through an electrophilic aromatic substitution reaction. Methyl benzoate is reacted with nitric acid and sulfuric acid at low temperatures. This results in a nitro group replacing a proton on the aromatic ring to form methyl m-nitrobenzoate. The product is recrystallized and has a melting point close to the literature value of 78°C. The percentage yield is calculated to be 77.84%, close to the theoretical yield.

Uploaded by

suraini
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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You are on page 1/ 6

OBSERVATIONS

1) To prepare and calculate the percentage yield of methyl m-nitrobenzoate by


electrophilic aromatic substitution.
2) To get the melting point of the m-nitrobenzoate.

INTRODUCTION
The nitration of Methyl Benzoate required an electrophilic aromatic substitution
reaction, in which the aromaticity of the ring system is preserved. For example,
benzene reacts with bromine to form bromobenzene. Many functional groups can be
added to aromatic compounds via electrophilic aromatic substitution reactions.
A functional group is a substituent that brings with it certain chemical reactions that
the aromatic compound itself doesn't display. In this experiment, nitro (-NO2) group
added on the benzene ring which there is an ester group attached to methyl benzoate.
Benzene is an organic chemical compound with the chemical formula C6H6. The
benzene molecule is composed of six carbon atoms joined in a ring with one
hydrogen atom attached to each. In this reaction, a proton of the aromatic ring is
replaced by a nitro group. Benzene was considered as aromatic because of its smell.
Nitration is one of the most important examples of electrophilic substitution reaction.

Nitration of methyl benzoate to prepare methyl m-nitrobenzoate is an example of


an electrophilic aromatic substitution reaction. A proton of the aromatic ring is
replaced by a nitro group.

APPARATUS
10mL and 150mL beaker, pasteur pipet, test tubes, measuring cylinder, weighing
balance,thermometer, vacuum filtration setup, Buchner funnel, melting point setup

MATERIALS
6mL and 2mL concentrated H2SO4, 3.05g methyl benzoate, ice, 2mL concentrated
nitric acid, cold water, 5mL ice cold methanol.
EXPERIMENTAL PROCEDURE
6mL of concentrated sulfuric acid were cooled in a 100mL beaker and 3.05g of
methyl benzoate added by using ice bath. The mixture was cooled to 0℃ or below
and 2mL concentrated sulfuric acid and 2mL concentrated nitric acid added using
Pasteur pipet slowly added to the mixture. During the addition of the acid, the mixture
was stirred continuously and the temperature was maintain below 15℃. After all the
acids added, the mixture was warm to the room temperature. After 15 minutes, the
acid mixture was poured over 25g of crushed ice in a 150mL beaker. After the ice was
melted, the product was isolated by vacuum filtration through a Buchner funnel and
washed into two 12mL portions of cool water and then two 5mL portions of ice-cool
methanol. The product was weighed and recrystallize it from an equal weight of
methanol. The melting point of the recrystallized product should be 78℃. The
percentage yield was calculated.
RESULTS
Observed melting point : 80℃
Mass of methyl benzoate : 3.053g
Mass of filter paper : 1.087g
Mass of watch glass : 34.766g
Mass of product : 5.360g
Mass of final product : 3.102g
Theoretical yield of methyl m-nitrobenzoate : 3.985g
Percentage yield of methyl m-nitrobenzoate : 77.84%

CALCULATIONS
No of mole of methyl benzoate = 3.053g / 136.149 g/mol
= 0.022 mol
No of mole of metyl benzoate = no of mole of methyl m-nitrobenzoate

Theoretical yield of methyl m-nitrobenzoate = 0.022 mol x 181.146 g/mol


= 3.985g

Percentage yield of methyl m-nitrobenzoate = 3.102g / 3.985g x 100%


= 77.84%
DISCUSSIONS
In this experiment, nitric acid and methyl benzoate were reacted to form methyl
m-nitrobenzoate. A process when an electrophilic aromatic substitution reaction that
involves the installation of a nitro group (NO2) on an aromatic ring called nitration.
Nitration is the most important examples of electrophilic substitutions.The Chemical
process to introduce nitro groups into an organic chemical compound. This process of
treating or combining with nitric acid or a nitrate especially conversion of an organic
compound into a nitro compound or a nitrate. Methyl benzoate (C6H8O2) known as
an aromatic hydrocarbon and a methyl ester with a colorless appearance. Methyl
benzoate also used perfumery. Methyl benzoate has a methyl ester group that
attached to its benzene ring.The ester group is the meta deactivator and the reaction
takes place at the meta position because the ortho and para positions are destabilized
by adjacent positives charges on the resonance structure.
From the experiment, the theoretical yield of methyl m-nitrobenzoate are 3.985g
produced 77.84% of its percentage yield. The observed melting point of this product
are 80℃ that close to the literature temperature.The melting point of the recrystallized
product should be 78℃. A few errors occurred throughout this experiment that
effected the percentage yield. During the transferring process of the crystallized
mixture into the filtration apparatus, some product may stuck in the beaker’s wall and
it was affected the weight of the final product produced lead to the smaller mass. The
product obtained maybe not dried 100% dried. The product should be dry overnight to
evaporate all the water moisture. So that, the percentage yield obtained can be
corrected. This lab session enhance the understanding and skills on how to prepare
methyl m-nitrobenzoate by electrophilic aromatic substitution.
CONCLUSIONS
As the conclusion, it can be conclude that, the methyl m-nitrobenzoate was
successfully prepared. The theoretical yield of methyl m-nitrobenzoate are 3.985g and
produced 77.84% of the percentage yield. The literature melting point for this product
should be 78℃. The observed melting point of methyl m-nitrobenzoate are 80℃ that
close to the literature temperature.

QUESTIONS
1) Why is methyl m-nitrobenzoate formed in this reaction instead of the ortho or para
isomers?
Because of the ester group of the starting product of methyl benzoate. The
functional group of ester is a electron withdrawing group causing nitrobenzene to
become in meta position

2) Why does the amount of the dinitration increase at high temperature?


Because of the activation energy required to substitute the nitro functional group
onto the aromatic ring, increase heat provide more energy.

3) Why is it important to add the nitric acid-sulfuric acid mixture slowly over a
15-minute period?
The rapid addition of the nitric acid and sulfuric acid mixture increase the chance
of side products forming.

4) Indicate the product formed on nitration of each of the following compound


benzene, toluene, chlorobenzene and benzoic acid.
5) Write full mechanism for the nitration of methyl benzoate.

REFERENCES
1) https://www.cliffsnotes.com/study-guides/chemistry/organic-chemistry-ii/reactions-
of-aromatic-compounds/electrophilic-aromatic-substitution-reactions
2) https://www.chemguide.co.uk/mechanisms/elsub/nitration.html
3) https://www.chemistryscore.com/glossary/nitration/
4) http://www.chemspider.com/Chemical-Structure.6883.html
5) https://www.sciencedirect.com/topics/agricultural-and-biological-sciences/methyl-b
enzoate

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