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Acetaminophen Lab Report

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Submitted By relrod
Words 713
Pages 3
Randall Elrod
12/6/2013
Acetaminophen

Title
Acetaminophen
Purpose
To prepare acetaminophen.
Theory
Acetaminophen is a synthetic, nonopiate, centrally acting analgesic derived from p-aminophenol.1 The full chemical name is N-acetyl-p-aminophenol.1 The pKa of acetaminophen is 9.51 at 25°C.1 Acetaminophen is used to relieve mild to moderate pain from headaches, muscle aches, menstrual periods, colds and sore throats, toothaches, backaches, and reactions to vaccinations (shots), and to reduce fever.2 Acetaminophen may also be used to relieve the pain of osteoarthritis (arthritis caused by the breakdown of the lining of the joints).2 Acetaminophen is in a class of medications called analgesics (pain relievers) and antipyretics (fever reducers).2 It works by changing the way the body senses pain and by cooling the body.2 Acetaminophen is one of the most commonly used medicines in the United States.3 When used according to the label directions, it has a well-established record of safety and efficacy.3 Although acetaminophen overdose is very rare in the context of its broad usage, overdose can be toxic and lead to acute liver failure.3 Preparation of acetaminophen involves treating an amine with an acid anhydride to form an amide.4 In this experiment, p-aminophenol (the amine) is treated with acetic anhydride to form acetaminophen (p-acetamidophenol), the amide. The chemical reaction for acetaminophen is as follows: 4

Procedure
Procedure is as taken from Pavia, Lampman, Kriz pages 43-44.4
The only deviation in this experiment was 0.67g of crude acetaminophen was used instead of 1g to recrystalize the sample because only 0.67g was produced during the production of acetaminophen.

Diagrams of equipment used:
Steam Bath

Gravity Filtration

Ice Bath

Vacuum Filtration

Table of Reagents
Reagent Structure Melting Point Boiling Point Density Solubility
(In water) p-Aminophenol 188 °C 284°C 1.29g/cm³ 1.5 g/100 mL (20 ºC)
Acetic Anhydride
-73.1 °C 140 °C 1.087g/mL REACTS with water
Acetaminophen
168-172 °C (lit.) No Boiling Point 1.293 g/cm³ 14 g/L (20 ºC)
Acetic acid
16.2 °C (lit.) 117-118 °C (lit.) 1.049 g/mL at 25 °C (lit.) Completely soluble with water *All data taken from Chemical Book Website5

Safety Precautions
Safety glasses are to be worn at all times and all chemical reactions were performed under vented hoods.

Observations
After adding Norite to the p-aminophenol and HCl solution the solution turned dark. After heating and filtering the color remained dark. After adding the buffer solution and acetic anhydride, the mixture was heated and then placed in an ice bath. Crystals were formed after approximately 15 minutes. Scratching the flask helped induce crystallization. The crystals were vacuum filtered, washed, and then dried for a week. The weight of the unpurified acetaminophen was 0.67g. After recrystallization and vacuum filtering, the purified sample weighed 0.08g and was lighter in color due to fewer impurities.

Results
Limiting Reagent and Theoretical Yield

The p-Aminophenol (C6H7NO) is the limiting reagent since it yields the least amount of Acetaminophen. 2.91g of C8H9NO2 is the theoretical yield.

% Yield

% Recovery of Recrystallization

Conclusion
The overall difficulty to this experiment was moderate. The only difficulty encountered was that the percent yield was low due to careless errors in the laboratory. These careless errors can be prevented in future experiments by using more precaution when weighing reagents and being more attentive when performing each step of the procedure.

References 1Remington's Pharmaceutical Sciences. 23rd ed. Easton, PA: Mack Publishing Company; 1995:1109-1110.
2"Acetaminophen: MedlinePlus Drug Information." U.S National Library of Medicine. U.S. National Library of Medicine, n.d. Web. 04 Dec. 2013. .
3"Drugs." Acetaminophen Toxicity. N.p., n.d. Web. 05 Dec. 2013. .
4Pavia; Lampman; Kriz, Introduction to Organic Laboratory Techniques Third Edition; Saunders College Publishing: 1988; pp 43-44.
5ChemicalBook---Chemical Search Engine. N.p., n.d. Web. 07 Oct. 2013. .

Questions

1.

2.
P-aminophenol has an alcohol functional group and since water has a lower pKa value than p-aminophenol, the p-aminophenol acts as the base and water as the acid.
Acetaminophen is an acidic drug, and is thus much less likely to ionize in aqueous solution.

3.

4.
Theoretical Yield

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