Procedure for Nitration of Methyl Benzoate

CHEM 225L.01

Purpose
The purpose of this experiment was to complete the nitration of methyl
benzoate by creating an electrophilic aromatic substitution reaction with the nitronium ion
produced from the reaction between nitric acid and sulfuric acid
Chemicals Used

12mL/4mL sulfuric acid; divided

6.1g methyl benzoate
4mL nitric acid
10mL cold methanol

Equipment Used
400mL beakers (2)
125mL Erlenmeyer flask
Buchner funnel
Vacuum filtration system

Procedure
Two ice water baths were prepared in two mL beakers and set aside. Then 12mL sulfuric
acid was added to an empty Erlenmeyer flask, which was placed into one of the ice water baths
prepared earlier for 3 minutes. After the allotted time, 6.1g of methyl benzoate was slowly
poured into the cold sulfuric acid in the Erlenmeyer flask.
4 mL of sulfuric acid and 4mL of nitric acid were obtained and poured into separate
graduated solutions. The two acids were then combined and placed in an ice-water bath for 3
minutes. The two acids were then added to the methyl benzoate/sulfuric acid solution and
swirled periodically during the addition. The solution was then removed from the ice-water bath
and set aside to reach room temperature for approximately 15 minutes. The solution was swirled
periodically during the 15 minutes of warming.
10mL of methanol was measured and added to a graduated cylinder and placed in an ice-
bath and set aside. Once 15 minutes passed, the now room-temperature solution was poured into
a 250mL beaker with 50g ice. After the ice has melted, solid precipitate was collected via
vacuum suction using a small Buchner funnel. A flask was then obtained and rinsed with cold
water. The solid was also rinsed with 30mL of cold water followed by a rinse with 10mL of cold
methanol. The product was subsequently dried under suction filtration for 5 minutes.
During the 5 minute wait, 10mL methanol was poured into a graduated cylinder and
placed on an ice-water bath. After the drying, the crude product was weighed and recorded. The
crude product was then placed into a 250 mL beaker and recrystallized with an equal amount of
volume of methanol to the crude product. The solution was then placed on a hot placed and
placed on “low” setting to dissolve the solid. Once it dissolved, it was removed from heat to cool
to room temperature. The recrystallized product was then collected via filtration suction using a
small Buchner funnel.
 A beaker was rinsed using a portion of 10mL cold methanol first. Then the solid was
rinsed with the remaining of cold methanol and placed under vacuum filtration for 10 minutes in
order to dry it. The weight of crude product was then obtained along with the percent yield.

Data Questions
1) Calculate the theoretical yield for the reaction.

6.54g/136.15g/mol= 0.048 mol methyl benzoate

Theoretical yield= 0.048mol=x/181.15g/mol= 8.702g

2) List the electrophile for this nitration lab.

NO2+, the nitronium ion
3) Calculate the percent yield for this lab.

Percent yield= 5.177g/8.702g x 100% = 59.5%

4) List the six types of EAS reactions.

Nitration, halogenation, sulfonation, chlorination, bromination, Friedel-Krafts Acylation

and Alkylation.

5) Identify the following substituents as either ortho and para directors or meta directors.

Ortho para director Meta director

Meta director
Ortho-para director

Ortho- para director Ortho-para director

a.

6) What does the acronym NAS stand for in organic chemistry?

Nucleophilic Aromatic Substitution (NAS)

7) List the two reagents that combined to produce the electrophile for this reaction.
 nitric acid and sulfuric acid

8) 8. What is the name of the aromatic compound used in this nitration reaction?
Methyl benzoate

9) What does the acronym EAS stand for in organic chemistry?

Electrophilic Aromatic Substitution (EAS)

10) What was the catalyst that was used for this reaction?

Sulfuric acid

Discussion
Nitration is the substitution of an NO2 group for a hydrogen on a benzene ring. Nitric and
sulfuric acid react to form a nitronium ion. This turns methyl benzoate into methyl-3-
nitrobenzoate. In this reaction, the nitro group is added in the meta position which is a 1,3
position.

The lab results do support the objective of the experiment, but unfortunately this material has yet
to be covered in lecture.