CHM 206 Expt 12
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Experiment 12: Nitration of Methyl Benzoate – A Macroscale Synthesis
Objective
The purpose of this experiment is to apply electrophilic aromatic substitution reactions and macroscale synthetic procedures to understand the activation and deactivation of substituents.
Table of Reagents
Reagent
Molar Mass (
g
mol
)
Melting Point (°C)
Safety
Sulfuric Acid
98.079
10.31
Causes severe skin burns and eye damage. Very strong acid and corrosive.
Nitric Acid
63.01
-43.6
Very strong acid and corrosive. May intensify fire, oxidizer. Causes severe skin burns and
eye damage. Wash any spills thoroughly.
Methyl Benzoate
136.15
-15
Harmful if swallowed. Keep away from heat and flames.
Methyl m-benzoate
181.15
78
Can cause eye and skin damage.
Reaction Equations/Experiment Equipment and Apparatus
General Safety
Any spills on clothes or skin should be reported to the TA right away in order to start the clean up process. If anything spills on you or your clothes go directly under the shower and rinse for 15 minutes and then follow up with NaHCO
3
.
Procedure
1.
Place 12 mL of concentrated sulfuric acid in a 100 mL beaker and cool to about 0 °C using an ice-water bath.
2.
Add about 6 mg of methyl benzoate using a graduated cylinder and cool again to 0 °C.
3.
Slowly add a cooled (0 °C) mixture of 4 mL of nitric acid and 4 mL of sulfuric acid using
a Pasteur pipet.
4.
Stir continuously with a glass rod and keep the temperature below 15 °C (ice bath).
5.
Allow the mixture to warm to room temperature and wait 15 minutes.
6.
Pour the reaction mixture onto ~50 g of ice in a larger beaker.
7.
Stir and filter the mixture once all the ice has melted.
8.
Wash the solids on the filter twice with 15 mL of cold water, then twice with 10 mL of cold methanol.
9.
Weigh the crude product and recrystallize from methanol.
10. Filter and dry the crystals on top of the Buchner funnel.
11. Determine the melting point (~78 °C) and record the IR Spectrum using the ATR source.
Observations
The temperature rose very quickly when adding methyl benzoate to the sulfuric acid. There was also vapor present.
The temperature would also rise quickly when adding the nitric acid and sulfuric acid mixture.
o
The color of the solution also turned yellow.
There was foaming present when adding the solution to the beaker with ice.
The two different crystals that came out as product were fluffy, white powders.
Data and Results
Volume of Methyl Benzoate (to use): 6
g
∗
1
mL
1.084
g
=
5.54
mL
Crude Weight: 5.832 g
Final Weight: 5.041 g
Theoretical Yield of Methyl m -Nitrobenzoate: 6
g Methyl
Benzoate
∗
1
mol Methyl Benzoate
136.15
g Methyl Benzoate
∗
1
mol Methyl m
−
Nitrobenzoate
1
mol Methyl Benzoate
∗
181.15
g Methylm
−
Nitrobenzoat
1
mole Methyl m
−
Nitrobenzoate
Percent Yield: 5.832
7.983
∗
100
=
73.05%
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