Makenna Grieco

Synthesis of Acetaminophen

Results & Discussion:

The objective of this experiment was to synthesize acetaminophen by the reaction of p-

aminophenol with acetic hydride.

Reaction of synthesis of Acetaminophen:

Table 1: Masses and Moles of Reactants and Products

Mass of p-aminophenol 1.50 g

Moles of p-aminophenol 0.0137 moles

Mass of acetaminophen 1.14 g

Theoretical yield of acetaminophen 2.07 g

Percent yield 55.1 %

Table 2: IR Peaks and Functional Groups of Acetaminophen

Peaks Functional Groups

3320.55 cm-1 O-H stretch for phenol; N-H stretch for amide

3106.50 cm-1 C-H stretch for aromatics

2791.82 cm-1 C-H stretch for alkanes

 1648.44 – 1504.66 cm-1 C-C stretch in ring for aromatics

Table 3: Melting Point Range of Acetaminophen

Initial Temperature Final Temperature

Acetaminophen 167C 169C

IR Spectrum of Acetaminophen

Calculations:

1. Determine the limiting reactant

1 mol 1 mol acetominophen

1.50 g p-aminophenol x × = 0.0137 moles acetaminophen
109.13 g 1mol p−aminophenol

p-aminophenol is the limiting reactant.

1.08 g 1 mol 1 mol acetominophen

2.0 mL acetic anhydride x x × = .036 moles
1 mL 60.05 g 1 mole acteic anhydride

acetaminophen
2. Determine theoretical yield

151.2 g
0.0137 moles acetaminophen x = 2.07 g acetaminophen
1 mole

4. Determine percent yield

1.14 g acetaminophen
= 55.1%
2.07 g acetaminophen

Through this experiment, acetaminophen was produced from p-aminophenol and acetic anhydride.

Based on the 1:1 mole ratio of the two reactants, and the molecular weights of the products and

reactants, the theoretical yield of acetaminophen was 2.07 g. The experimental yield was 1.14 g. There

was a 55.1 % yield. The melting point range of acetaminophen was found to be 167-169°C. The

expected melting point for acetaminophen is 168-172 °C .1

The IR spectrum helped confirm that the product made was acetaminophen. An O-H stretch for

phenol and N-H stretch for amide was found at 3320.55 cm-1, a C-H stretch for aromatic was found at

3106.50 cm-1, a C-H stretch for alkanes was found at 2791.82 cm-1, and a C-C stretch in the ring for

aromatic was found at 1648.44-1504.66 cm-1. These peaks correspond with bonds found in the molecule

acetaminophen.

The melting point of a substance can be used to determine the purity of that substance. The

acetaminophen that was synthesized was found to be a pure sample because the melting point range is

considered a sharp range. A sharp range is considered to be a < 2 ° difference. The experimentally found

range was 167-169 °C, which exactly has a 2 ° difference. The experimental range found was also not

distant from the expected range of 168-172 °C.

The experimental yield was much lower than the theoretical yield; this could have been due to

some error that occurred during the experiment. Since the experimental yield was lower this indicates

there was a loss of product. Some sources of error could include not cooling the solution long enough
during recrystallization or heating it too strongly. For recrystallization, when the solution is heated and

then cooled. Then once the solution is cooled and the impurities have been filtered out, the solute that

remains will precipitate or crystalize. If the solution did not have enough time to cool, some product

could be left in the solute, which would cause there to be less product. Another source of error for the

decrease in product could be from when the impurities were removed some of the product was also

eliminated. This would also cause the overall product to be less than it was expected to be.

References
1. https://www.sigmaaldrich.com/catalog/product/usp/1003009?lang=en&region=US

Questions:

1. Rank this Results & Discussion section on a scale of 1 – 10 (1-poor, 10-excellent):

I would give this results and discussion section a 7 out 10. The section is easy to follow, and

I know exactly what was performed in the experiment. The tables are very organized and

have good descriptive titles. The calculations did not have descriptions, so you had to figure

out what each calculation was calculating. Also, during the discussion portion, some

experimental procedures and background information were stated, and they should have

not been. For example, “Once the solution is heated, it is cooled to room temperature then placed

in an ice bath,” should not be included because it is giving a procedural detail.

2. Does this Results & Discussion give the reader a comprehensive explanation of the results of the

experiment? Are you able to follow what was learned from the experiment?

Yes, I was able to easily follow along and I knew exactly what was performed in the

experiment. They gave the reader their results and explained how and why this substance

was acetaminophen. They also included sources of error and the effects they would have

had on their final product.

 3. Is a ChemDraw figure included of the overall reaction and/or product?

No, there is no ChemDraw figure present of the overall reaction and/or product.

4. Are the data tables and calculations presented in a clear and understandable fashion?

Yes, the data tables are presented in a clear and understandable fashion with clear

descriptions for the tables, but there are missing descriptions for the calculations.

5. Do the data tables have detailed titles?

Yes, the data tables have clear, concise titles.

6. Is there a clear explanation of the results and was the data used to support the results?

Yes, they did a decent job in explain their results with their data, especially when they

explained the IR spectrum.

7. Were sources of errors used to help explain outcomes of the experiment such as a low percent yield

or impure product?

Yes, they did a good job at explaining how their sources of error affected their outcomes in

the experiment.

8. Was there any unnecessary information included?

Yes, they included unnecessary procedure details and background information the

discussion section of the report.

9. Were references used properly throughout the report with in-text citations? Did the citations use

ACS style formatting?

Yes, they used the ACS style formatting for citations correctly.

10. Was the results & discussion well-written in a scientific style?

Yes, the writer organized their ideas well and wrote in a scientific style as they did not use

the first or second person.