Sample Lab Report

Preparation of Methyl m-nitrobenzoate via Nitration

Surname, Given Name , M.I Comment [e1]: Should contain your
name, date and title of the
Department of Chemical Engineering, Faculty of Engineering experiment
University of Santo Tomas
Espana, Manila

Abstract Comment [e2]: Briefly tell the

reader what you did in the
experiment, your results and a
Nitration is an example of electrophilic aromatic substitution, and in this experiment the brief conclusion.
Comment [e3]: Abstract is usually
goal was to successful add a nitro group to methyl benzoate using nitric acid and sulfuric composed of about 100 words

acid as a reagents, and vacuum filtration and centrifugation for isolation. The percent yield

from the original reagents was 26%, and the nitro group was successfully added to the

aromatic structure, which can be seen in the IR spectra of the final product.

Introduction Comment [e4]: This gives the reader

background information on your experiment and
what you did in the experiment and why
Nitration is an example of an electrophilic aromatic substitution reaction, where a
1,2
nitro (NO2) group is being substituted for a hydrogen on an aromatic compound . This is Comment [e5]: Provide reference to
statements lifted from books,
journals, etc. make sure these
achieved by the formation of the nitronium ion via protonation of nitric acid from sulfuric sentences are paraphrased.

acid. The nitronium ion is a strong enough electrophile, and can react with the aromatic

compound (in this experiment Methyl benzoate) to form an arenium ion intermediate. The

arenium ion is then deprotonated to reform the aromatic ring and yield the final product

(Methyl-m-nitrobenzoate) with the newly attached nitro group.

Aromatic substitution reactions are important synthetic reactions that are used to

make a variety of products including high-performance plastics and acetylsalicylic acid

(more commonly known as aspirin). In a study published in 2001 in the Journal of the

American Chemical Society, aromatic ether linkages can be effectively created using

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nucleophilic aromatic substitution (SNAr).3 Polyarylene ethers are examples of aromatic

ether linkages that are found in nature and can be synthesized using aromatic substitution.

The most common use of polyarylene ethers are in high-performance engineering plastics.

Another example of electrophilic aromatic substitution is the Kolbe reaction, where

carbon dioxide is used as the electrophile (instead of the nitro group, which would be

nitration).2 This reaction is used in the synthesis of aspirin. The Kolbe reaction creates

salicylic acid when sodium phenoxide attacks a carbon dioxide molecule, then undergoes

tautomerization to form sodium salicylate, which is then protonated to form the salicylic

acid. The salicylic acid is then reacted with acetic anhydride to synthesize acetylsalicylic

acid, or aspirin. Aspirin is a high selling commercial drug that utilizes electrophilic

aromatic substitution reactions, and various other forms of substitution reactions are used for

a variety of syntheses.

Experimental Section Comment [e6]: Tells the reader what

you did experimentally.

A. Chemicals and Reagents Comment [e7]: Use sub-headings and

write in past passive voice.

All chemicals used in this experiment were provided by the PLU stockroom, and the

infrared spectrometer, the melting point apparatus, and the centrifuge machine in the open

lab were also used. A vacuum filtration system was also assembled and used to isolate the

product.

B. Synthesis of Methyl-m-nitrobenzoate

Methyl-m-nitrobenzoate- From the lab manual, the procedure was followed and .210

(.0016 mol) methyl benzoate was added to a tared 3-ml conical vial, and then weighed to

determine the actual weight of the methyl benzoate. 1 0.45 ml (.008 mol) concentrated

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sulfuric acid was added to the vial and the vial was then attached to an air condenser (to help

hold the vial in place). The vial and air condenser were then submersed in a 250-ml beaker

ice-bath. A chilled mixture of .15 ml (.0033 mol) concentrated nitric acid and .15 ml (.002

mol) sulfuric acid was added drop wise via a Pasteur pipette over a period of 15 minutes,

through the air condenser into the vial. Once the acid was added, the reaction mixture was

allowed to acclimate to room temperature in a 250-ml beaker with a water bath at room

temperature for 15 minutes unstirred. After the mixture had sat, it was transferred via

Pasteur pipette into a 20-ml beaker containing 2.0g crushed ice. The ice was allowed to melt

and then the mixture (white and chunky consistency) was vacuum filtered using a Hirsch

funnel wand washed with two 1-ml portions of cold water and two 0.3-ml portions of ice

cold methanol. Once dried, the crude product was weighed and then added to a Craig tube

for recrystallization.

C. Recrystallization and Determination of Percentage Yield

For recrystallization, methanol was boiled using an Erlenmeyer flask on a hot plate

and then 4 drops of methanol was used to dissolve the crude product in the Craig tube. After

being dissolved, the mixture sat at room temperature for approximately 5 minutes and then

was submersed in an ice-water bath for another 5 minutes for crystallization to occur. The

Craig tube was then placed in the centrifuge machine to isolate the crystals from the mother

liquor. The final product, Methyl-m-nitrobenzoate, was weighed using a watch glass, percent

yield was calculated, melting point measured, and an infrared reading was taken.

Final weight: .08g

Percent Yield: 26%

Melting Point: 76.6°C-78.9°C

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Results and Discussion Comment [e8]: Report only the important
data here. You may refer to the guide questions
in your lab manual for additional discussions.
In this experiment, methyl benzoate underwent an electrophilic substitution reaction

to form Methyl-m-nitrobenzoate, where a nitro (NO2) group was added to the methyl

benzoate in the meta position.

The Methyl Benzoate (1) was first mixed with concentrated sulfuric acid (2), then a

mixture of concentrated sulfuric acid and concentrated nitric acid (3) was added.1 The

sulfuric acid /nitric acid mixture was necessary to form the nitronium ion from the nitric

acid. Nitric acid isn’t a strong enough electrophile to react with the aromatic benzene ring,

but the nitronium ion with the positive charge on the nitrogen is a strong electrophile and

can react with the double bond of the methyl benzoate.

Figure 1 - Nitronium Ion Formation Comment [e9]: Include molecular

“pictures’ when you are reporting
mechanism of a reaction. Don not
The addition of the nitric/sulfuric acid mixture was added drop-wise over a period of forget to caption each figure

15 minutes to reduce the amount of by-product that could be formed in the reaction. The
Comment:
addition of the mixture allowed the nucelophile (methyl benzoate) to attack the electrophilic
Discuss the theoretical aspects
nitronium ion forming the arenium carbocation intermediate. Then the conjugate base from of the experiment. These can
be found in any organic
the deprotonation of the sulfuric acid (HSO4-), removes a proton from the meta-intermediate chemistry textbooks or
journals.
to reform the aromatic ring structure, and yielding the final product, Methyl-m-

nitrobenzoate.

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 Comments:

If you have any graphs or

tables they should also be put
here.

Never put a graph, structure,

equation, spectrum or table in
a report without giving it a
label and referring to it
somewhere in the text. (e.g.,
Figure 2 - Nitronium addition to Methyl benzoate Figure 1. 13C NMR spectrum
of oleic acid.)
Once the acid was added, the mixture was cooled without stirring, then added to

crushed ice to stop the reaction. The crude product was isolated via vacuum filtration, then
Comment:
impurities were removed using hot methanol and centrifugation. The percent yield of the On certain occasions you may
need to site certain literature.
experiment was 26%, and calculations are shown at the end of the paragraph. The melting
For example, if you are
point of the final product was 76.6°C-78.9°C, which compared to the literature value (78°C) identifying a compound based
on its melting point, you
was close enough to suggest a successful addition of the nitro group.1 The IR spectra also should tell the reader what the
literature value is for the
shows the characteristic aromatic ring stretches (3092.51, 1500-700, and 670), and at compound and reference your
source. You will also have to
reference your lab book
1525.84 the nitro group stretch which indicates that the experiment was successful in adding

the nitro group.

Percent Yield Calculations:

As seen in Figure 02, there are 3 resonance arenium carbocation intermediates, with

the positive charge at either the ortho, para, or meta position. The major product is the meta

product due to the carboxyl and nitro groups both being powerful electron withdrawing

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groups. The meta attack on the methyl benzoate is the only attack that doesn’t yield have a

resonance structure that isn’t highly unstable, so the meta attack is the most resonance

stabilized (compared to the attack at either the ortho or para positions). Comment [e10]: Discuss the mechanism
of reaction when you write a formal
report which involves a synthesis
While the percent yield was a little low for the experiment, the melting point data reaction.

and the IR spectra both support the notion that the nitro group was successfully added to the

methyl benzoate. Additional reading on the subject allowed for the defense of the meta

attack as opposed to the ortho or para attack of the nitro group, which was a successful

learning opportunity to see “nature’s laziness”, or the desire to form the structure with the

most stability and lowest energy of activation.

References: Comment [e11]: Include all

references used in your formal
report. Use APA style for
1) Engel, R.G.; Kriz, G.S.; Lampman, G.M.; Pavia, D.L. Introduction to referencing

Organic Laboratory Techniques: A Mircroscale Approach, Third Edition;

Brooks/Cole: Pacific Grove, CA, 1999.

2) Fryhle, Craig B., Solomons, T.W. Graham. Organic Chemistry: Eighth

Edition; John Wiley & Sons Inc.: Hoboken, NJ, 2004.

3) Chung, Sik Im and Kim, Snag Youl. “Meta-Activated Nucleophilic

Aromatic Substitution Reaction: Poly(biphenylene oxide)s with

Triflouromethyl Pendent Groups via Nitro Displacement.” Journal of the

American Chemical Society, 2001. 11071-11072