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Lab Report EXP.5 CHM457 Fund. Organic Chemistry

The document is a laboratory report for an experiment to prepare methyl nitrobenzoate from methyl benzoate. Key details include: - The objective was to prepare methyl nitrobenzoate and determine the percentage yield and melting point of the product. - Methyl benzoate reacted with the nitronium ion formed from nitric and sulfuric acids to form methyl nitrobenzoate. - The percentage yield of methyl nitrobenzoate was 8.19% and the melting point was 74°C. - In conclusion, methyl nitrobenzoate was successfully produced from the reaction, though the percentage yield was low, possibly due to errors in the addition of reagents.

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Husnul Hakim
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1K views6 pages

Lab Report EXP.5 CHM457 Fund. Organic Chemistry

The document is a laboratory report for an experiment to prepare methyl nitrobenzoate from methyl benzoate. Key details include: - The objective was to prepare methyl nitrobenzoate and determine the percentage yield and melting point of the product. - Methyl benzoate reacted with the nitronium ion formed from nitric and sulfuric acids to form methyl nitrobenzoate. - The percentage yield of methyl nitrobenzoate was 8.19% and the melting point was 74°C. - In conclusion, methyl nitrobenzoate was successfully produced from the reaction, though the percentage yield was low, possibly due to errors in the addition of reagents.

Uploaded by

Husnul Hakim
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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FAKULTI SAINS GUNAAN UNIVERSITI TEKNOLOGI MARA

CAWANGAN SELANGOR KAMPUS SHAH ALAM CHM 457 –


FUNDAMENTAL OF ORGANIC CHEMISTRY
LABORATORY REPORT

NAME: MOHAMAD HUSNUL HAKIM BIN MOHD HARIS FADZILAH

MATRIC NUMBER: 2022800758

GROUP: AS2451M3

EXPERIMENT TITLE: EXPERIMENT 5: Nitration of Methyl Benzoate

LECTURER: PROFESOR MADYA DR MOHD TAJUDIN B.


MOHD ALI
EXPERIMENT 5: Nitration of Methyl Benzoate

OBJECTIVE:

i. Preparation of methyl nitrobenzoate from methyl benzoate.


ii. To determine the percentage yield of product.
iii. To determine the melting point of the product.

INTRODUCTION:

Nitration of a benzene ring involves the addition of a nitro group. The electrophile
in this reaction is the nitronium ion. This nitronium ion is created by reacting nitric acid
with sulfuric acid. There are two steps to this process. First, a proton from the sulfuric
acid is added to the —OH group on the nitric acid. This forms water, which is a good
leaving group. Water leaves as the oxygen with a negative charge forms a double bond
with oxygen. Thus, forming the nitronium ion.

In this experiment, methyl benzoate is reacted with the nitronium ion to form methyl
nitrobenzoate. In the first step, the benzene ring acts as a nucleophile and attacks the nitrogen
in the nitronium ion. This leaves a positive charge on the benzene ring. Then sulfuric acid
removes the hydrogen from the same carbon that the nitronium ion is bonded to. The electrons
from the hydrogen bond are moved into the benzene ring, which reforms the conjugated
system.
The nitronium ions thus formed is sufficiently electrophilic to add to the benzene ring,
temporarily interrupting ring resonance.

At the end of the experiment, determine the percentage yield of the product and it melting point.
DATA:
Mass of methyl benzoate = 3.05 g
Weight of watch glass + filter paper = 33.4329 g
Weight of watch glass + filter paper + crude product = 34.0109 g
Weight of crude product = 0.578 g
Weight of watch glass = 33.3528 g
Weight of watch glass + final product = 33.6849 g
Mass of final product = 0.3321 g
Melting point of final product = 74°C

CALCULATION:

Mole methyl benzoate = Mass


Molar mass

3.05
= = 0.0224 mol
136

1 mole methyl benzoate 1 mole methyl nitrobenzene


0.0224 mol methyl benzoate 0.0224 mol methyl nitrobenzene

Mass of methyl nitrobenzene:

Mass = mole x molar mass


= 0.0224 x 181
= 4.0544 g (theoretical value)

Percentage yield of methyl nitrobenzene:

Percentage yield = Actual yield x 100


Theoretical yield

0.3321
= x 100
4.0544

= 8.19%
DISCUSSION:

In this experiment, methyl nitrobenzene can be prepared from reaction between methyl
benzoate and nitric acid. nitric acid was used to form the electrophile, the nitronium ion. The
sulfuric acid aided in the formation of the nitronium ion by donating a proton to nitric acid.
Methyl benzoate was the nucleophile in this reaction. Ice chunks were used in this reaction to
help the product crystallize out of the solution. Water and methanol were added to remove
impurities from the product. The equation for this reaction is:

The percentage yield of the product is 8.19%. A few errors occurred throughout the
experiment that could have affected the percent yield. For example, insert the nitric acid
mixture to fast in beaker containing crush ice. Because of this, the crystallization process
cannot occur perfectly. Way to overcome this error is use dropper and drop very slowly the
nitric acid mixture. The melting point of the final product is 74°C.

CONCLUSION:

In conclusion, methyl nitrobenzene can be produced from reaction between methyl benzoate
and nitric acid. The percentage yield of methyl nitrobenzene is 8.19% and the melting point is
74°C.
QUESTION:

1. Why is methyl m-nitrobenzoate formed in this reaction instead of the ortho or para
isomers?

- This is because the carboxylic group which is present in the functional group
withdraws the electron density from the ring. This makes it difficult for the
electrophilic substitution as there will be not any negative charge formed in the ortho
and para position. The meta position is deactivated towards nitration.

2. Why does the amount of the dinitration increase at high temperatures?

- The amount of the dinitration increase at high temperatures because activation energy
decreases as the temperature is higher.

3. Why is it important to add the nitric acid-sulfuric acid mixture slowly over a 15-minute
period?

- It increases the yield of the desired product.

4. Interpret the infrared spectrum of methyl m-nitrobenzoate.

- The infrared of methyl m-nitrobenzoate shows several characteristic peaks. The


aromatic ring has several C-H peaks characteristic of meta-substituted benzene at
750-800 wavenumbers. The ester carbonyl C=O. group has a peak at about 1730
wavenumbers.

5. Indicate the product formed on nitration of each of the following compound: benzene,
toluene, chlorobenzene, and benzoic acid.

i) Benzene,
ii) Toluene,

iii) Chlorobenzene,

iv) Benzoic acid,

REFERENCE:

1. https://www.studocu.com/row/document/university-of-botswana/organic-chemistry-
lab-ii/lab-334-nitration-of-aromatic-compounds-preparation-of-methyl-m-
nitrobenzoate-lab-report/7302720

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