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Experiment 5: Introduction to Green/Sustainable Chemistry: Synthesis of Aspirin
Report Sheet Kendal Miletich Tues, 8:30am
9/29/2020 Lab Section_____________
(e.g., Tues, 8am)
Part A. Synthesis of Aspirin
1. Data: Fill in the appropriate data from your notebook and from Part 2 calculations:
Mass of Salicylic Acid_______________ 3.502g
Volume of Acetic Anhydride__________ Moles of Salicylic Acid 0.02536mol
____________ 8.64g Grams of Acetic Anhydride ____________ 0.0846mol Moles of Acetic Anhydride ____________ Products:
Mass of 50 mL Beaker ______________ Mass of Beaker + Product 32.797g
____________ Mass of Aspirin Moles of Aspirin 28.534g
Percent Yield of Aspirin
__________________ 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.
3.502g C7H6O3 X 1mol C7H6O3/138.1g C7H6O3 = 0.02536mol b. Number of moles of acetic anhydride added to the reaction.
8mL C4H6O3 X 1.080g/1mL = 8.64g C4H6O3
8.64g C4H6O3 X 1 mol C4H6O3/102.1g C4H6O3 = 0.0845mol C4H6O3 c. Limiting reagent for the synthesis of the aspirin (show calculation and/or explain).
3.502g C7H6O3 X1mol C7H6O3/138.1g C7H6O3 X 1 mol aspirin/1mol C7H6O3 X 180.2g aspirin/1mol aspirin =
4.569g aspirin X 1mol aspirin/ 180.2g = 0.0236mol aspirin-->Limiting reagent is salicylic acid
8.64g acetic anhydride X 1 mol acetic anhydryde/102.1g acetic anhydryde X 1mol apsirin/1mol acetic aspirin X
180.2g aspirin/1mol apsirin = 15.24g aspirin
15.24g X1mol aspirin/180.2g aspirin = 0.08457mol aspirin d. Number of moles of acetylsalicylic acid produced.
4.2630g C9H8O4 X 1mol C9H8O4/180.2g = 0.02351mol C9H8O4 53 e. Percent yield for the synthesis of aspirin.
0.02351/0.02536 X 100 = 92.71% Part B. Analysis of Aspirin and Test for Purity
Substance Observations When
With Ferric Chloride Conclusions Salicylic Acid very dark purple salicylic acid is present Commercial Aspirin slight purple color on crystals, no purple liquid some salicylic acid present Aspirin no purple at all no salicylic acid present Postlab Questions
1. List two principles of green chemistry present in this experiment. Provide a brief explanation
for your choices.
We used atom economy- this means that we tried to incorporate every material that we used in this experiment.
We also used hazard and accident prevention- we used Nederman hoods to prevent toxic fumes from
inhalation, as well as designated waste disposal. 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
a.) A polymer is substance made up of a long chain of smaller molecules that link up and make bigger
b.) PolyAspirin is seen as much safer than other drugs, such as aspirin. This is because PolyAspirin which
passes through a persons lower intensine, where the environment is more basic, and then the drug forms fibers
by extrusion. Aspirin can cause bleeding, stomach ulcers and damage the stomach lining. Since the process of
PolyAspirin is safer, it can be used to for drug delivery. 54
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