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(ELECTROPHILIC AROMATIC
SUBSTITUITION
NITRATION OF METHYL UPLOADED BY
BENZOATE (ELECTROPHILIC Idayu Razali
AROMATIC SUBSTITUITION

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EXPERIMENT 5 ; NITRATION OF METHYL BENZOATE (ELECTROPHILIC

 AROMATIC SUBSTITUITION)

Objectives

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

electrophilic aromatic substituition.
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2) To get the melting point of the product.
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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.The reaction is shown below :

HNO3 + 2H2SO4  NO2+ + H3O+ + 2HSO4- 

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 equation has been shown below:

NITRATION OF METHYL BENZOATE (ELECTROPHILIC AROMATIC SUBSTITUITION  D O W N LO A D

In this experiment , a cool solution of the aromatic ester that has been
dissolved in sulphuric acid and nitric acid . This highly exothermic reaction is kept
under control by cooling then the mixture is poured into ice.The solid product is

isolated by filtration is isolated by filtration and recrystallizationfrom methanol which is

very soluble. This is the mechanisms of for nitration of methyl benzoate:

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Result and observation

Melting point for 1st= 75˚C - 78˚C 

2nd= 76˚C - 78˚C 

From the literature boling point which is melting point for methyl m-nitrobenzoate whic
is 78-80˚C, we can conclude that the product that we get is methyl m-nitrobenzoate.

Mass of methyl benzoate=3.0500g

Mass product=39.2225 g

Mass filter paper = 0.6963 g

Mass final product = 2.6996 g

The chemical equation :

C6H5CO2CH3 + H2NO3  C6H4CO2CH3NO2 + H2O

Number mole of C6H5CO2CH3

Molar mass of C6H5CO2CH3 = 136.1487

Mass of C6H5CO2CH3 = 3.0500g

Number of mole = 3.0500g / 136.1487

= 0.022 mol

1 mol of C6H5CO2CH3 needed to produce 1 mol of C6H4CO2CH3NO2

0.022 mol of C6H5CO2CH3 needed to produce 0.022 mol of C6H4CO2CH3NO2 

Molar mass of C6H4CO2CH3NO2 = 181.1463

The theoretical yield of C6H4CO2CH3NO2 = 0.022 mol x 181.1463 g/mol

= 3.9852 g

 Actual yield = 38.5262 g

Percentage yield of product = (2.6996 g / 3.9852 g) x 100%

= 67.74%

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 .

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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 75˚C - 78˚C and 76˚C - 78˚C , the value is closed to the literature value which
is 78˚C . 

  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

The methyl m-nitrobenzoate 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 75˚C - 78˚C and 76˚C - 78˚C. From the given physical constant
we know that the literature melting point of methyl m-nitrobenzoate is 78 - 80˚C , so
we can conclude that the product we get is methyl m-nitrobenzoate.

References

1) http://www.webassign.net/sample/ncsumeorgchem2/lab_5/images/figure1.png 

2)http://www.intech.mnsu.edu/groh/weblabs/mebnnitration/mechanism/MethylBenzoateNitration
MechEnd.htm# 

3) http://allfreepapers.com/print/Nitration-Methyl-Benzoate/2209.html 

4) http://en.wikipedia.org/wiki/Nitrobenzene 

5) htt // l / bh ? h # li t
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5/30/2018 NITRATION OF METHYL BENZOATE (ELECTROPHILIC AROMATIC SUBSTITUITION | idayu razali - Academia.edu
5) http://www.google.com.my/webhp?source=search_app#sclient=psy-
ab&q=2)%09nitotoloune+images&oq=2)%09nitotoloune+images&gs_l=hp.3...411146.416231.18.416
488.18.18.0.0.0.1.1412.5320.0j9j4j3j1j7-1.18.0.cqrwrth..0.0.0..1.1.16.psy-
ab.8_9_h3z7uKc&pbx=1&bav=on.2,or.r_qf.&bvm=bv.47534661,d.bmk&fp=b59eb3ee5481059a&biw
=1366&bih=667 

6) http://www.google.com.my/webhp?source=search_app#sclient=psy-
ab&q=nitrobenzoic+acid+images&oq=nitrobenzoic+acid+images&gs_l=hp.3..33i21.68252.77599.19.7
7984.24.24.0.0.0.2.902.7558.0j11j3j2j2j4j1.23.0.cqrwrth..0.0.0..1.1.16.psy-
ab.ov3PzGy_rCE&pbx=1&bav=on.2,or.r_qf.&bvm=bv.47534661,d.bmk&fp=b59eb3ee5481059a&biw
=1366&bih=667 

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