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Chemistry Nucleophilic Aromatic Substitution Experiment

Chemistry Internship (The University of Texas Rio Grande Valley)

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Experiment #2 Nucleophilic Aromatic Substitution

Jessica Lopez
CHEM 2125 – 07
Dr. Mito
September 21, 2017

Objective:
The purpose of this experiment was to “identify the product of a nucleophilic aromatic
substitution reaction of 3, 4- dichloronitrobenzene with sodium methoxide.” (Stranz,1)
Introduction:
Nucleophilic Aromatic substitution reactions offer a useful way to functionalize an aromatic
ring. The high pi electron density of an aromatic ring results in predominant reactivity towards
electrophiles; however, if the aromatic ring is activated with electron withdrawing groups ortho-,
para- to a good leaving group, a nucleophilic substitution reaction is possible. Halogens are the
most common leaving groups for nucleophilic aromatic substitution reactions and functional
groups such as –NO2, NR2, -CF3 and –CN are electron withdrawing enough to render the
aromatic ring susceptible to reaction with an electron – rich nucleophile, such as an amine.

The figure
above shows the reaction of 3, 4- dichloronitrobenzene with sodium methoxide.

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The figure above shows the mechanism of 3, 4- dichloronitrobenzene with sodium methoxide.
The only path that this mechanism would have been able to take would be path B.

Materials:
The equipment used in this experiment:
- 50 mL round bottom flask
- 150 mL beaker
- 400 mL beaker
- Graduated cylinder
- Thermometer
- Condenser
- Rubber tubing
- Hot plate
- Separatory funnel
- Ice bath
- Buchner funnel
- Flask
- Filter paper
- Spatula
- DigiMelt
- Capillaries
- Water/methanol solution
- 0.166 3, 4-dichloronitrobenzene (C 6 H 3 Cl2 NO2)
- 15 mL methanol (CH 4 / MeOH ¿
- 10 mL 25%sodium methoxide in metanol (NaOMe)

Procedure:
1. We gathered our materials to set up the reflux apparatus including the stand, a rubber
clamp, and 50 mL round bottom flask, condenser, plastic clamp, and a hot plate. We then
gathered our chemicals 15 mL of methanol, 10 mL of 25% NaOMe, added to that two
boiling chips and the flask was then placed onto the hot plate. We allowed our solution to
begin to boil then started the timer for one hour.
2. We prepared an ice bath in a 400 mL beaker around the 45 minute mark to prepare for the
next part of the experiment.
3. We waited for the hour to be up and after that we set the round bottom flask aside
allowed it to cool for about 10 minutes then adding it to an empty 150 mL beaker. We
then added 25 mL of water to our product and allowed it to precipitate.
4. When the water was added it was for the most part fully precipitated but it needed a little
more so we proceeded to add it to the ice bath for around 5 minutes to fully precipitate
the liquid. After it was fully precipitated we assembled our vacuum to filter the

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precipitate out. We put the filter paper onto the funnel, adding a bit of water so that way it
none of our product would go into the flask.
5. Next the 60:40 water/methanol solution was prepared with 6 mL‘s of water and 4 mL’s
of methanol into a 10 mL graduated cylinder. We then poured our product into the
vacuum and washed it out with the water/methanol solution.
6. Allowing our product to dry on the filter paper, we then weighed the mass of our product
on a watch glass. We set up the digimelt was plugged in and we put our product into two
capillaries and the meting point was recorded.

Results:
Moles of 3, 4- Dichloronitrobenzene:
1mol
0.166g 3, 4- dichloronitrobenzene = 0.00086 mol of 3, 4- dichloronitrobenzene
192 g/mol
3, 4-dichloronitrobenzene

Theoretical yield:
(mass of the 3,4-DCNB/molar mass of 3,4- DCNB) * (1 mol product/1mol of 3, 4-
DCNB*Molar mass of sodium methoxide)
(0.166g 3,4-DCNB/192 g 3, 4- DCNB)*( 1 mol of product/1 mol of 3,4- DCNB*54.02 g/mol
NaOMe) = 0.047
Percent yield:
(Mass of recovered product/ Theoretical yield) * 100%
(0.173g /0.047)*100% = 368 %
Discussion:
Our experiment was successful due to the fact that we obtained a great amount of product and I
believe that the modification to the experiment made it run a lot smoother than if we had to use a
sand bath, and also because at times the lab manual is unclear. Our only downfall was not
knowing the correct value for the temperature in the beginning of the experiment because in the
lab manual there were two temperatures that were stated.
Conclusion:
The objective of this experiment was to “identify the product of a nucleophilic aromatic
substitution reaction of 3, 4-dichloronitrobenzene with sodium methoxide.” (Stranz, 1). Our
experiment was considered successful, because we were able to obtain a great amount of product
and as well find the melting point of our product using the DigiMelt which was between the
temperatures of 58 - 98 degrees celcius.

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References:
Stranz, Michael. Signature Lab Series. Cengage Learning 2008
Mito, Shizue. Pre Lab Notes

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