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Experiment 5: Introduction to Green/Sustainable Chemistry: Synthesis of Aspirin

Report Sheet
Brian Dale 10/7/20
Name____________________________ Date______________ Lab Section_____________
Tues 1pm
(e.g., Tues, 8am)
Part A. Synthesis of Aspirin
1. Data: Fill in the appropriate data from your notebook and from Part 2 calculations:
Starting Materials:
2.48 g
Mass of Salicylic Acid_______________ 0.18
Moles of Salicylic Acid ____________
8.53 g
7.9 mL Grams of Acetic Anhydride ____________
Volume of Acetic Anhydride__________
0.836
Moles of Acetic Anhydride ____________
Products:
29.49 g
Mass of 50 mL Beaker ______________ Mass of Beaker + Product 39.39 g
____________

Mass of Aspirin 2.9 g

_______________ Moles of Aspirin 0.02
__________________

Percent Yield of Aspirin 58.5%

____________

2. Calculations: Show calculations for the following (density of acetic anhydride is 1.080 g/mL)
a. Number of moles of salicylic acid added to the reaction.
1 mol salicylic acid = 138.06 g
grams used in experiment = 2.48

2.48/138.06 = 0.18 mol

b. Number of moles of acetic anhydride added to the reaction.

1 mol acetic anhydride = 102.06 g
grams used in experiment = 8.53 g

8.53/102.06 = 0.836 mol

c. Limiting reagent for the synthesis of the aspirin (show calculation and/or explain).
The limiting reagent for this was salicylic acid, because the reaction between salicylic acid and acetic anhydride
is a 1:1 ratio.

d. Number of moles of acetylsalicylic acid produced.

1 mol acetylsalicylic acid = 180.16 g
grams synthesized in experiment = 2.9 g

2.9/180.16 = 0.02 mol acetylsalicylic acid

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e. Percent yield for the synthesis of aspirin.
actual yield = 2.9 g
theoretical yield = 4.96 g

2.9/4.96 = 0.585
0.585 * 100 = 58.5% yield

Part B. Analysis of Aspirin and Test for Purity

Observations When
Substance Reacted Conclusions
With Ferric Chloride

Salicylic acid deep purple color impure

synthesized asprin small dots of purple slightly impure
commercial asprin small dots of purple slightly impure
Postlab Questions
1. List two principles of green chemistry present in this experiment. Provide a brief explanation
for your choices.
One principle of green chemistry in this experiment is atom economy. This was demonstrated by using a
reaction that in theory works on a 1:1 ratio, thus minimizing waste products. Another principle demonstrated
was the use of a catalyst, which in this case was phosphoric acid.

2. Aspirin is taken by millions to treat pain and prevent heart disease and blood clots and. Oldest
versions of aspirin date back to Hippocrates (460-370 BC) where the active ingredient was
obtained from willow tree bark. A more recent version, PolyAspirin, is a polymer that was first
synthesized by an undergraduate student at Rutgers University. Please address the following:
(a) What is a polymer? (b) Read the C&E News article on polymers for drug delivery (available
on the LAB course site) and describe how the structure of PolyAspirin can be exploited for drug
delivery.
a. A polymer is a substance made of similar units bonded throughout the material.

b. PolyAsprin can be used for better drug delivery throughout the body in the long run. Regular asprin can
damage such things as the stomach lining and cause ulcers if ingested too frequently, but PolyAsprin doesn't
break down in the stomach's acidic enviroment, instead hydrolizing safely in the intestines where it is more
basic. This property can be used elsewhere in the body for drug delivery not intended for specific enviroments.

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