Faculty of Applied Science

Bachelor of Science (Hons.) Applied Chemistry

CHM457
FUNDAMENTAL ORGANIC CHEMISTRY
LABORATORY REPORT

Experiment : experiment 5:( NITRATION OF METHYL BENZOATE)

Name : Muhammad Firdaus Hakimi bin Mohd Zulkarnain

Student ID : 2022494668

Name of Partners : AININ SOFIA BINTI NOORDIN (2022494468)

NUR HIDAYAH MOHD NAJIB (2022800226)
MUHAMMAD QAID IRFAN BIN KAMARULAZAMAN (2022659932)
Name of Lecturer : Dr. Najmah PS. Hassan

Date of Experiment : 29/11/2022

Date of Submission : 6/12/2022

Allocated Mark Mark

Objectives 2
Introduction 3
Procedure 3
Results 4
Calculations 4
Discussions 6
Conclusion 2
Questions 5
References 1
Total 30
OBJECTIVES
 To prepare and calculate the percentage yield of methyl m-nitrobenzoate by electrophilic
aromatic substitution.
 To observe the melting point of methyl m-nitrobenzoate

INTRODUCTION
Aromatic substitution is typically electrophilic. This is caused by the benzene ring's high density. One
of the ingredients in many useful and necessary natural compounds is the benzene ring. The species
responds by producing additional useful items. The species responds to other useful items. A positive
ion or the tip of a dipole is frequently the species that reacts with the aromatic ring.
Nitration is one of the main instances of electrophilic substitution. The nitronium ion, which is
produced from nitric acid via protonation and water loss, serves as the electrophile in nitration, with
sulfuric acid serving as the dehydrating agent. The following describes the response:
HNO3 + 2H2SO4  NO2⁺ + H3O⁺ + 2HSO4ˉ
When an aromatic substrate is allowed to react with an appropriate electrophilic reagent, numerous
aromatic substitution processes are known to occur, and many additional groups besides nitro may be
introduced to the ring. At a temperature of 50°C, methyl benzoate can be nitrated using a solution of
concentrated nitric acid and sulfuric acid; the electrophile is the nitronium ion, whose synthesis is
aided by the concentrated sulfuric acid's reaction with the nitric acid.

PROCEDURE
1) 6 mL of concentrated sulfuric acid was cooled to about 0 ℃ in a 100-mL beaker and 3.05 g of
methyl benzoate was added.
2) The mixture was cooled to 0℃ or below by using an ice-salt bath and very slowly add, using
a Pasteur pipet, a cool mixture of 2 mL of concentrated sulfuric acid and 2 mL of
concentrated nitric acid.
3) The mixture was stirred continuously during the addition of the acids and the temperature of
the reaction was maintained below 15℃. If the mixture rises above this temperature, the
formation of the product increases rapidly, bringing about a decrease in the yield of the
desired product.
4) The mixture was warmed to room temperature after all of the acid were added.
5) The acid mixture was poured over 25 g of crushed ice in a 150-mL beaker after 15 minutes.
6) The product was isolated by vacuum filtration through a Buchner funnel after the ice had
melted and it was washed with two 12-mL portions of cold water and then with two 5-mL
portions of ice-cold methanol.
7) The product was weighed and it was recrystallized from an equal weight of methanol.
8) The melting point of the recrystallized product should be 78 ℃.
9) The percentage yield was calculated and the product was submitted to the instructor in a
labelled vial.
RESULTS
Empty beaker = 197.6805 g
Beaker + ice = 223.3005 g
Watch glass + filter paper = 34.63 g
Watch glass + filter paper + crystal = 35.5 g
Weight of crystal = 0.87 g
Weight of crystal after recrystallization = 0.31 g
Observed melting point of product = 70℃ - 80℃

CALCULATIONS
Theoretical yield calculation of methyl m-nitrobenzoate
Theoretical yield of 𝐶6𝐻4C𝑂2C𝐻3𝑁𝑂2
= 0.0224 mol × 181.14 g/mol
= 4.0575 g
Actual yield of methyl m-nitrobenzoate
∴ Actual yield = 0.31 g
Percentage yield calculation of methyl m-nitrobenzoate

Percentage Yield (%)

Experimental Yield
= X 100
Theoretical Yield
0.31 g
= X 100
4.0575 g
= 7.64%
DISCUSSION
In general, nitration is the process that starts when nitrogen dioxide reacts with an acidic chemical
molecule. This experiment led to the production of methyl m-nitrobenzoate by nitrating methyl
benzoate. To avoid a violent reaction and to keep the temperature constant, all the reagent was
introduced gradually. Electrophilic aromatic replacements in this procedure entail the substitution
of an electrophile that becomes a substituent for a proton on an aromatic ring. The methyl
benzoate is protonated by the solvent sulphuric acid, producing the resonance stabilized arenium
ion in the intermediate meta position. Because the ortho and para positions of the resonance
structure are made unstable by nearby positive charges, the ester group is the metabolic
deactivator and the reaction takes place at the meta position.
The meta product is the main item. This is since both carboxyl and nitro groups are potent
electron withdrawing groups. The yield of methyl m-nitrobenzoate from this experiment is 0.31 g,
whereas the theoretical yield is 4.0575 g. The yield calculated as a percentage is 7.64%. The
melting point that has been measured is between 70 ℃ and 80 °C. This range is good because
exactly with number reported in the literature which is 78 ℃.
Apart from that, sulfuric acid is highly corrosive and can cause severe burns, while nitric acid is
known to be one of the strongest oxidizing agents. is needed. Be sure to clean the spatula, filter
flask, and reaction tube. After that, be sure to return the bottle cap and do not return it unused.
Original bottles of chemicals and reagents. Methanol is a flammable and toxic liquid and must be
used judiciously. Additionally, all chemicals must be disposed of properly in the containers
provided. It is very important to keep the temperature of the chemical reaction mixture below
15°C.

CONCLUSION
In conclusion, we have successfully prepared methyl m-nitrobenzoate. The theoretical yield of
methyl m-nitrobenzoate is 4.0575 g, but the actual yield is 0.31 g. The calculated percentage
return is 7.64%. The measured melting point of our products is 70-80°C. As a result, the purpose
of this experiment was achieved.

QUESTIONS
1) Because methyl benzoate is an electron withdrawing unit and a meta director. The
electron density at ortho and para position is less and incoming electrophile will attack
position where the electron density is high that is at the meta position.
2) The amount of dinitration increase at high temperatures because the activation energy
decreases as the temperature is higher.
3) The reaction generates a lot of heat, too much and will it will give effect to the yield of
product.
4) Benzene produces nitrobenzene. Toluene produces o-nitro toluene and p-nitro toluene.
Chlorobenzene produces m-nitrochlorobenzene. Benzoic acid produces m-nitrobenzoic
acid.
REFRENCES
 Laboratory Manual of Fundamental Organic Chemistry (CHM457)
 Nur Syuhada Binti Ridzuan, Nur Iliya Syifa Binti Razali, Noor Izzah Nadhirah Binti Muhamad
Zahidi, Nurul Syahilah Binti Hisham, and Nurul Najwa Binti Mohd Shaffie. “Experiment 5:
Fundamental Organic Chemistry Lab Report CHM 457”. Retrieved on 3/12/2022 from
https://pdfcoffee.com/experiment-5-fundamental-organic-chemistrylab-report-chm-457-
pdf-free.html
 bartleby. Chapter 43, Problem 1Q. “The reason for the formation of methyl mnitrobenzoate
instead of ortho and para isomers in the following reaction needs to be explained”.
Retrieved on 4/12/2022 from
https://www.bartleby.com/solutionanswer/chapter-43-problem-1q-ebk-a-small-scale-
approach-to-organic-l-4thedition/9781305446021/67e9233b-8e40-46de-82c4-a56061ef520f