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Chemistry
Date
Jan 9, 2024
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Uploaded by Habibaabdelfattah
Habiba Elaaidy
12/5/2022
Nitration of Methyl Benzoate
Aim
The purpose of this experiment is to synthesize methyl nitrobenzoate from
methyl benzoate; Using Nitric acid and Sulfuric acid through electrophilic aromatic
substitution reaction.
Introduction
Aromatic situation reactions are a type of organic reaction where an atom that is
attached to the aromatic system is replaced by an electrophile. These reactions tend to
be electrophilic due to a high electron density within the ring of benzene. An electrophile
is positive ion that is trying to bond with another inorder to get more electrons, these
positively charged ions want to react with the aromatic ring.
The most common
mechanism for electrophilic aromatic substitution is the arenium ion mechanism. The
arenium ion mechanism refers to carbocation that is attached to the benzene ring.
Table of Physical Properties and Hazards
Compound
Name
Molecular
Structure
Molecular
Formula
Molecular
Weight
g/mol
Boiling
Point
(°C)
Melting
Point
(°C)
Hazard and Toxicity
Methyl
benzoate
C
8
H
8
O
2
136.15
199°C
-15°C
Harmful if swallowed
Nitric acid
HNO₃
63.01
83°C
-42°C
May intensify fire; oxidizer
Causes severe skin burns
and eye damage
Fatal if inhaled
Sulfuric acid
H₂SO₄
98.079
337°C
10°C
Causes severe skin burns
and eye damage
Ethanol
C₂H₆O
46.07
78.37°C
-114.1°C
Highly Flammable liquid
and vapor
Methyl
3-nitrobenzoate
C8H7NO4
181.04
279 °C
80 °C
May cause eye irritation.
May cause skin irritation.
May be harmful if
absorbed through the skin.
May cause irritation of the
digestive tract.
Procedure
To complete this experiment, first, prepare an ice bath, and then in two
small test tubes, place 0.5 mL of Nitric acid in one and 0.6 mL of sulfuric acid in the
other. Allow the test-tubes to sit on ice for 10 minutes, then using a glass pipet, transfer
the nitric acid dropwise into the tube of the sulfuric acid. In Erlenmeyer flask, place o.5
mL of Methyl benzoate and 1.o mL of sulfuric acid, and place the mixture on ice the
nitrating solution was then placed dropwise into the Erlenmeyer flask allow the flask to
sit in the ice bath for 30 mins mixing every 5 minutes. Place 1o mL of chilled water into
a clean beaker and slowly mix in the solution into the beaker. Allow it to sit for 5
minutes. And set up a vacuum filtration system then filter out the crystals.
Results
Mass of Final Product =
0.515 g
Theortical Yeild
Mass of methyl benzoate= 0.54 g
(0.5 mL)
Mass of nitric acid= 0.71g (0.5 mL)
Mass of sulfuric acid= 2.94g (1.6 mL)
Moles of methyl benzoate= 0.54 g/136.1487 g/mol= 0.00397 mol (limiting reagent)
Moles of nitric acid= 0.71 g/63.01284 g/mol= 0.01128mol
Moles of sulfuric acid= 2.94 g/98.07848 g/mol= 0.02997 mol
(0.00397 mol)( 181.1463 g/mol)=
0.71915 g
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Percent Yeild
(0.515 g/0.71915 g) x 100 =
71.61%
We where able to successfully achieve a 71.61% yield from this experiment.
Refrences
PubChem. (n.d.-a).
Ethanol
. PubChem. Retrieved December 11, 2022, from
https://pubchem.ncbi.nlm.nih.gov/compound/Ethanol#datasheet=LCSS
PubChem. (n.d.-b).
Methyl 3-nitrobenzoate
. PubChem. Retrieved December 11, 2022,
from https://pubchem.ncbi.nlm.nih.gov/compound/Methyl-3-nitrobenzoate
PubChem. (n.d.-d).
Methyl benzoate
. PubChem. Retrieved December 11, 2022, from
https://pubchem.ncbi.nlm.nih.gov/compound/Methyl-benzoate#datasheet=LCS
S§ion=GHS-Classification
PubChem. (n.d.-e).
Nitric acid
. PubChem. Retrieved December 11, 2022, from
https://pubchem.ncbi.nlm.nih.gov/compound/nitric_acid
PubChem. (n.d.-f).
Sulfuric acid
. PubChem. Retrieved December 11, 2022, from
https://pubchem.ncbi.nlm.nih.gov/compound/Sulfuric-Acid#datasheet=LCSS&s
ection=GHS-Classification
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