Scipaper in Chemlab

Discussion
Nitration is an introduction of nitrogen dioxide into a chemical

compound acid . In the process the methyl benzoate was nitrated to form a
methyl m-nitro benzoate . The reagents were added very slow to avoid a
vigrous reactions and the temperature was maintained low to avoid
formation of dinitro product .
In this experiment , electrophilic aromatic substituitions involved the
replacement of a proton on an aromatic ring with an electrophile that
becomes substituent. The solvent sulphuric acid protonates the methyl
benzoate , creating the resonance stabilized arenium ion intermediate . The
electron deficient nitronium ion reacts with the protonated intermidiate meta
position . 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 .The
major product is the meta product due to carboxyl and nitro groups both
being powerful electron withdrawing groups.
The actual yield methyl 3- nitrobenzoate crude product is 2.6996 g
while the theoretical yield is 3.9852 g .The percentage yield that we get is
67.74%.The melting point is 75C - 78C and 76C - 78C , the value is
closed to the literature value which is 78C .
As we know sulphuric acid are extreamly corrosive and can cause
severe burns while nitric acid is one of the strong oxidizing agent so we need
to wear gloves while doing an experiment. Methanol is toxic and we need to
use in well ventiled space only for example fume board . All of the
chemical material should be discarded properly in the container provided.
Conclusion
Nitration is a general class of chemical process for the introduction of

a nitro group into an organic chemical compound.. The methyl mnitrobenzoate was prepared. The theoretical yield is 3.9852 g while tha
actual yield is 2.6996 g so we get the percentage yield is 67.74%. The
melting point of our product is 75C - 78C and 76C - 78C. From the
given physical constant we know that the literature melting point of methyl
m-nitrobenzoate is 78 - 80C , so we can conclude that the product we get

is methyl m-nitrobenzoate.
Introduction
Aromatic substituition is electrophilic; due to high density in benzene
ring.Benzene ring is one of components in most important natural products and
other useful products. The species reacting with the aromatic ring is usually a
positive ion or the end of a dipole.
Nitration is one of the most important examples of electrophilic
substituition.The electrophile in nitration is the nitronium ion which is generated
from nitric acid by protonation and loss of water , using sulphuric acid as the
dehydrating agent.
In this experiment we will put nitro group on a benzene ring which already has ester
group attached to it.The actual electrophile in the reaction is the nitronium ion ,
which is generated in the reaction mixture using concentrated nitric acid and
concentrated sulphuric acid.
The objective of this experiment is to prepare and calculate the percentage yield of
methyl m- nitrobenzoate by electrophilic aromatic substitution as well as getting the
melting point of the product.
References
1.
2.
3.
George A. Olah and Stephen J. Kuhn, "Benzonitrile, 2-methyl-3,5-dinitro-", Org. Synth.; Coll. Vol. 5:
480
E. O. Woolfolk and Milton Orchin, "2,4,7-Trinitrofluorenone", Org. Synth.; Coll. Vol. 3: 837
Melvin S. Newman and H. Boden, "2,4,5,7-Tetranitrofluorenone", Org. Synth.; Coll. Vol. 5: 1029
4. Perrin, C. L.; Skinner, G. A. (1971). "Directive effects in electrophilic aromatic substitution ("ipso
factors"). Nitration of methyl benzoate". Journal of the American Chemical Society93 (14): 3389Z
5. Prakash, G.; Mathew, T. (2010). "Ipso-Nitration of Arenes". 49 (10): 17261728
Methodology
For the experiment in Nitration of Methyl Benzoate, the conical flask was preweighed. Then 10 drops of methyl benzoate should be added to determine the
weight of methyl benzoate used by the difference. The conical flask was containing
the methyl benzoate was placed in an ice bath. 2ml of concentrated H2SO4 were
also added drop wised to the conical flash while swirling then it was set aside. The
nitrating agent was prepared in a clean test tube that has been chilled in an ice
bath. The Pasteur pipet was also used then the nitrating agent was slowly added to
the methyl benzoate solution prepared in Step 1. Addition of the nitrating agent
must not be less than 15 minutes. If cloudiness occurs, add a few drops of
concentrated H2SO4 until the mixture becomes clear. The reaction mixture stood for
15 minutes in a water bath at room temperature. 10g of crushed ice were also
added into the reaction mixture and stirred vigorously. Once all the ice has melted,
the solid product were separated formed by the vacuum filtration. The product
obtained were washed with cold distilled water, followed by 5% NaHCO3 and finally
again with cold distilled water until the filtrate becomes neutral. The products in a
pre-weighed watch glass were place and dried over a steam bath. Then the weight
of the product were determined. The product were re-crystallized with methanol as
directed in Appendix A and the percentage yield were calculated. The TLC profile
and melting point of the re-crystallized product were obtained and then the product
were properly labeled.

Scipaper in Chemlab

Uploaded by

Copyright:

Available Formats

Scipaper in Chemlab

Uploaded by

Document Information

Original Description:

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Scipaper in Chemlab

Uploaded by

Copyright:

Available Formats

Discussion

Nitration is an introduction of nitrogen dioxide into a chemical

Nitration is a general class of chemical process for the introduction of

m-nitrobenzoate is 78 - 80C , so we can conclude that the product we get

You might also like