Organic Principles Lab- Acetominophen

Seton Hill University

Bartelson – Spring 2017

Name: Austin McLean

Date: 5-7-17

Title: Synthesis of Acetaminophen

ABSTRACT: In this experiment, an acetaminophen was synthesized through a reaction between p-

aminophenol and acetic anhydride, with H3PO4 as the catalyst. The product of this reaction was
purified and recrystallized. An IR was taken of the acetaminophen which had peaks in the alkyl halide
functional group and aliphatic amine functional group. The melting point rage of the acetaminophen
was also taken which was 170 degrees C to 174 degrees C.

REACTION SCHEME:

+ —> +

Catalyst: H3PO4

DATA/RESULTS:

Structure of Product: Molecular Weight: 151.163 g/mol

Melting point (observed in lab): 170 degrees C

 Organic Principles Lab- Acetominophen
Seton Hill University
Bartelson – Spring 2017
Melting point (literature value): 169 degrees C

YIELD OF PRODUCT
Limiting reagent: P-aminophenol
Moles of limiting reagent: 13.74 mmol
Moles of product expected: 21.158 mmol
Theoretical yield (in grams): 2.077 g
Actual yield: 0.92 g
Percent yield: 44.29 %
QUESTIONS:
Organic Principles Lab- Acetominophen
Seton Hill University
Bartelson – Spring 2017
Calculations:
• 1.5 g X (1 mol / 109.126 g) = 0.0137
0.0137 X 1,000 = 13.74 mmol —> Calculation for mmol
of P-aminophenol
• 2 mL X (1.08 g/mL) = 2.16 g —> Calculation for grams
of acetic acid
• 2.16 g X (1 mol /102.09 g/mol) X 1,000 mmol = 21.158
mmol —> Calculation for mol of acetic acid
• 13.74 mol X (1 mol / 1,000 mmol) X (151.163 / 1 mol) =
2.077 g —> Calculation for theoretical yield
• (0.92 g / 2.077 g) X 100 = 44.29 % —> Calculation for
percent yield
 Organic Principles Lab- Acetominophen
Seton Hill University
Bartelson – Spring 2017
1 Why was the solution heated and then cooled during the recrystallization of the crude
acetaminophen?

To remove impurities from the crude acetaminophen through heating, and then allow crystals to
form from the cooling.

2 Give two reasons why the product in most reactions is not pure. How is the melting
point of a product used to determine purity?

The slightest difference can cause impure compounds to form in a solution. Impurity can also
come from the reactants not reacting completely. I f substance has a small melting point
range with a range difference of only one or two degrees C, then it is mostly pure. A
larger melting point range would indicate impurities in a substance.

3 Phenacetin (shown below) is another over-the-counter antipyretic and analgesic. Write an

equation for the synthesis of phenacetin.

+ —>
 Organic Principles Lab- Acetominophen
Seton Hill University
Bartelson – Spring 2017
REFERENCES:

http://www.foothill.edu/psme/armstrong/recrystallization.shtml

https://www.coursehero.com/file/p2lac26/Two-reasons-why-the-crude-product-in-most-reactions-is-
not-pure-is-because/

http://www.stolaf.edu/people/hansonr/chem253/expt4_2008_phenacetin.pdf

http://www.wiredchemist.com/chemistry/instructional/laboratory-tutorials/determination-of-melting-
point