CHEM 123L - Experiment 1

Experiment 1
Synthesis of Acetaminophen
Clifford Tse
20529845
Partner Raminder Dhanoa
TA Xiao Qi
CHEM 123L - 012
February 6, 2014
CHEM 123L Experiment 1
Clifford Tse - 20529845
Introduction
Acetaminophen, also commonly known as Tylenol, is an over-the-counter medicine
used to relieve pain and reduce fevers. Within this experiment, Acetaminophen will be
formed through the reaction between p-aminophenol and acetic anhydride. This reaction
will incur Acetaminophen as a crude solid being impure, which will be purified further
through the use of a recrystallization technique. The purification process involves
dissolving a solid and recrystallizing as a crystal solid from the solution. The process is
follow by heating the crude solid to dissolve using a minimal amount of solvent, often
referred to as recrystallization solvent. It is then cooled to room-temperature and cooled
even further in an ice-bath in order to have the crystals solidify within the saturated
solution. Both impure and purified crude solids will be obtained through vacuum filtration,
a technique used to separate the solvent and solid through vacuum pressure.
(Stathopulos, 2014)
The purpose of this experiment is to determine the melting point of the crude solid,
Acetaminophen, in both impure and purified solids. This is accomplished through the
process of recrystallization. The crude solids will then be extracted through the use of
vacuum filtration and further accessed in determining the melting point. The melting
points are determined through using an apparatus known as MelTemp. The experimental
melting point values determined are then used to be compared with theoretical listed
ranges of pure Acetaminophen.
Experimental Procedure
The experimental procedure used for this experiment was outlined in the CHEM
123L lab manual, Experiment #1. All steps were followed without deviation.
Experimental Observation
Mass of p-aminophenol
Mass of 125mL Erlenmeyer
3.00g
54.50g
Flask
Mass of Crude Products with
57.64g
125mL
Mass of Crude Products
Volume of Deionized Water
3.14g
31.4mL
Added
Mass of Purified Products with
57.01g
125mL
Mass of Purified Products
Melting Point of Crude
2.51g
160C -
Product
Melting Point of Purified
165C
160C -
Product
163C
Results and Calculations

C6H7NO
(s)
+ C4H6O3 (aq) C8H9NO2 (s) + C2H4O2 (aq)
Theoretical Yield
C6H7NO
C4H6O3 (aq)
(s)
Mp-aminophenol = 109.13 g/mol
d = 1.08 g/mL
m = 3.00 g
V = 4 mL
n = m/M
M = 102.09 g/mol
n = 0.0274 mol
m=dxV
m = 4.32 g
n = m/M
n = 0.0423 mol
C6H7NO
Mass of Acetaminophen
m=Mxn
m = (151.16 g/mol) (0.0274 mol)
m = 4.14 g
Percent Yield
Yield=
Actual Yield
100
Theoretical Yield
3.14 g
100
4.14 g
= 75.8 %
Discussion
(s)
is the limiting reactant

Within this experiment, the experimental melting point of both the crude and
purified products have been determined to be 160 C - 165 C and 160 C - 163 C
respectively. When comparing with the theoretical data of Acetaminophens melting point
to be within the range of 169 C - 170 C, the experimental values prove to be fairly close
with less than 10% deviation in range values. When comparing the melting point of the
experimental value and theoretical value, the purified products melting point is used as
it has complete the recrystallization process sustaining a more similar characteristic to
the theoretical sample with respect to its properties. When looking at the values, there
appears to be no significant differences between the crude and purified product, thus
shows no real benefit in solely comparing the purified product only because of possible
experimental deviations.
Although the experiment appears to have highly accurate results when comparing
experiment and theoretical values, it would appear as though possible errors may have
incurred along the process. Some issues that may have been raised include the
instrumental accuracy of measuring proper proportions of acetic anhydride and paminophenol. The result of having lesser amounts of p-aminophenol would have led to a
lower yield, and ultimately a lower yield percentage. Additionally, the melting point was
determined through the use of the MelTemp apparatus, which utilizes a thermometer
while looking through a small eye piece to observe physically. This process may have
resulted in possible procedural errors as the process could have been difficult to evaluate
due to the small eye piece and keeping track of temperature ranges.
Throughout this experiment, the overall recrystallization process of Acetaminophen
appears to have a yield percentage of 75.8%, lacking almost 25% from the expected
theoretical value. The lack of yield may be the result of the above stated errors incurred.

The experiment a whole, accurately follows through the conceptual theory of chemistry
throughout the entire process.
Questions
1.
a. In this experiment, each 10 mL of water was added for every 1 g of crude
product produced. This is due to the solution retaining its saturated state,
where 10mL per 1 g of crude is the correct ratio to sustain the solution. If 5 mL
of water were to be added as the ratio instead, the solution would become
supersaturated, resulting in having an effect to the recrystallization process.
b. If 15 mL of water was added for every 1 g of crude product, the solution would
become unsaturated. There would be an excess amount of water within the
ratio thus affects the purity of the product since more of the crude product
would be required.
c. If the room temperature was used rather than a cold solvent in aiding the
transfer of recrystallized products, the solubility of the crystals would be higher,
thus incurring a possible loss in crystals during the vacuum filtration process.
This in turn, would result in a loss of yield and ultimately affects the overall
yield calculations.
d. The purpose of scratching the inner walls of the round bottom flask is to initiate
the recrystallization process through the crystal growth stage.
2. Within the field of chemistry, the definition of an organic compound is a compound
that contains carbon (Petrucci, et al., 2011).
3.
Amine:
Amides:
(Wikimedia, 2014)
4. The aspirin, a salicylate drug, is a commonly used drug used to relieve minor aches,
pains and reducing fevers. It is also known as acetylsalicylic acid. Similar to

Acetaminophen, both are produced through organic synthesis. Acetylsalicylic acid is
synthesized from salicylic acid and acetic anhydride, producing acetic acid; C7H6O3 +
C4H6O3 C9H8O4 + C2H4O2 (About.com Chemistry, 2014) The salicylic acid is required
to further continue the process of esterification to reduce irritation as a result of the
phenol group pertained in salicylic acid. In doing so, this has produced a product
similar to Acetaminophen, while sustaining better taste with less irritation. Aspirins are
now commonly seen around the world and used as an everyday drug to benefit lives
everywhere.
Conclusion
The experiment performed has demonstrated the reaction between p-aminophenol
and acetic anhydride, producing Acetaminophen and acetic acid. The reaction occurred
results in a crude product identified as impure Acetaminophen. Purification of the product
is performed through the process of recrystallization. Samples of both the crude and
purified products are taken and used to determine the experimental melting point. These
values are then used to compare with theoretical data and assess the accuracy and
reliability of the experiment. With the crude and purified products of Acetaminophen
having an experimental melting point of 160 C - 165 C and 160 C - 163 C
respectively, the theoretically melting point being 169 C - 170 C deems a fairly
accurate result, having less than 10% in deviation between values. Additionally, the yield
of the products are determined through comparing experimental and theoretical yields of
the reaction. With the crude product having a percentage yield of 75.8%, lacking almost
25% from theoretical calculations, deviations that may have influenced this result could
be deemed through instrumental and procedural errors. These errors include the

accuracy of the equipment, along with performing the experiment under the limitation of
being a human.
References
Department of Chemistry 2014 Chemistry Laboratory Manual Fall 2014. University of

Waterloo, Waterloo. (pp. 12-15).
Petrucci, R. H., Herring, F. G., Madura, J. D., & Bissonnette, C. (2011). General chemistry:
Principles and modern applications. (10 ed., pp. 248-252, 274). Toronto, Ontario:
Pearsons Canada Inc.
Wikimedia. "Amine." Amine.
http://en.wikipedia.org/wiki/Amine (accessed February 3, 2014).
Wikimedia. "Amide." Amide.
http://en.wikipedia.org/wiki/Amide (accessed February 3, 2014).
About.com Chemistry. How to Make Aspirin - Acetylsalicylic Acid.
http://chemistry.about.com/od/demonstrationsexperiments/ss/aspirin.htm.
(accessed February 3, 2014).

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Experiment 1

CHEM 123L Experiment 1

Clifford Tse - 20529845

CHEM 123L Experiment 1

Clifford Tse - 20529845

CHEM 123L Experiment 1

Clifford Tse - 20529845

Results and Calculations

+ C4H6O3 (aq) C8H9NO2 (s) + C2H4O2 (aq)

Mp-aminophenol = 109.13 g/mol

is the limiting reactant

CHEM 123L Experiment 1

CHEM 123L Experiment 1

CHEM 123L Experiment 1

Clifford Tse - 20529845

CHEM 123L Experiment 1

CHEM 123L Experiment 1

Department of Chemistry 2014 Chemistry Laboratory Manual Fall 2014. University of

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