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“YACHAY TECH”
ORGANIC CHEMISTRY I
PRACTICE 4:
ESTERIFICATION REACTION:
PREPARATION OF ASPIRIN
Authors:
Luzuriaga Espinoza Kenia Michelle
Palma Loor María Daniela
Professor:
Hortensia Rodriguez, Ph.D.
Date:
10 - Jun - 2021
SEMESTER I - 2021
❖OBJECTIVES
● To learn and understand the concepts and process of synthesizing an ester from a
carboxylic acid and an alcohol in the presence of sulfuric acid.
● Learn and understand the concepts and process of synthesizing aspirin from its
corresponding acid and alcohol anhydride.
❖INTRODUCTION
➢ ESTERS
An ester structure is a carbonyl with an alkyl or aryl group (R) on one side and
oxygen attached to another alkyl or aryl group (R ') on the other side,
represented by the general formula: RCOOR'. Esters in chemistry comprise a
complex family of organic compounds, which are used in various
pharmaceuticals, among other products for human use, such as the production
of household cleaning products. These compounds are mostly found naturally
in different plants, fruits, and flowers. When these compounds are rightly
combined with other compounds with volatile properties, they can produce
various fruity aromas.
This complex is not very stable and stabilizes towards the energetically more
favorable molecule, which is the ester, releasing a water molecule and a proton
(H+). The proton is then used to regenerate the sulfuric acid:
Figure 1: Scheme of the mechanism of action of Fischer-Speier esterification
❖REAGENTS
● Carboxylic acid
● Alcohol
● Sulfuric acid
❖PROCEDURE
Fisher Esterification
Alcoholysis of acid anhydride: ASPIRIN Synthesis
❖ OBSERVATIONS
Esterification
For this experiment, the melting point could not be obtained because the melting point
as such was not found during the virtual session of this practical.
Synthesis of Aspirin
FeCl3 test
❖RESULTS
Esterification
The possible 7 aromas that we would have achieved in practical presence are:
propyl acetate smells like pear, isoamyl acetate smells like banana, octyl acetate
smells like orange, butyl butyrate smells like pineapple, ethyl butyrate smells like
strawberry, methyl butyrate smells like apple, and methyl anthranilate smells like
grape.
Then, we compare the ester aroma to find the corresponding structure. For
example, a strong scent of pears means that you made propyl acetate.
Studies have shown that the alkoxy oxygen comes from the alcohol, not the
carboxylic acid. So, we'll split the ester diagram at the carbon-oxygen single bond
and fill in the missing OH and H to get the starting materials. For example, if we split
propyl acetate at that bond, add an OH to the carbonyl carbon and add a hydrogen
to the alkoxy oxygen, we get acetic acid and 1-propanol as the starting materials
Synthesis of aspirin
For the aspirin synthesis process, the amount of salicylic acid used was 2,020 g
according to the weight on the balance. Thanks to the synthesis process between
salicylic acid and acetic anhydride in a H2SO4 concentrate, a first phase of our aspirin
could be obtained, which was called crude aspirin in which a loss of mass could already
be witnessed, this loss can be produced by the retention of some product in the
equipment used for the synthesis.
Then, we worked with the first crystallization of the aspirin when it was cooled, but not
before taking a sample of our raw aspirin, in order to make the FeCl3 test.
Next, a purification process was performed, which in this case was a recrystallization,
during this process of our raw sample, it was possible to observe a change in terms of
the original amount with which we worked and the remaining of our raw sample
This is due to a possible loss in the equipment and the filtration that was performed
because the recrystallization is performed to purify the product because that loss
contained impurities that were retained inside the crystals during the filtration process
and then were eliminated by the recrystallization. This can be confirmed by the FeCl3
test.
In this practice, the ferric chloride technique is used to identify the product formed and
determine its purity, since through this test it is possible to determine the presence of
phenol groups. The first test carried out was on a salicylic acid sample, obtaining a
purple color due to this compound containing phenols. Then the crude aspirin test
obtained in the first crystallization was carried out, obtaining a violet color that
indicated the presence of salicylic acid (reagent used in the synthesis) for which it was
necessary to perform recrystallization of the product, also during this process it was
done another test in the mother liquor and, as expected, the test was also positive for
the presence of phenols.
The test carried out after recrystallization presented a yellow color that showed us that
the decision to carry out the second recrystallization to purify our product was correct,
however, it is avoidable thinking that despite having performed recrystallization there
is a qualitatively notable difference possibly due to the fact that there are still
remnants of salicylic acid in the recrystallized product.
Table 2: Qualitative results of ferric chloride test in each of the different solutions of the process
❖CONCLUSION
● Through this practice, we understood the concepts of crystallization, which is the
most useful method to purify solid substances. To perform this process, it is
necessary to choose a good solvent with a greater difference between the hot
and cold solvents. In addition, it was possible to observe through the virtual
laboratory the synthesis of aspirin, also known as acetylsalicylic acid, and how
FeCl3 helped us to verify the impurities of the substance and the presence of
phenols.
● The recrystallization process allowed a high purification of the synthesized aspirin
that is corroborated by the ferric chloride test, which is an ideal qualitative test to
identify purity and determine the presence of phenolic compounds in the
synthesis of acetylsalicylic acid.
❖QUESTION/ANSWERS
1. Write a balanced equation for the Aspirin synthesis (draw correctly all the
structures).
The central oxygen of the acetic anhydride attacks the hydrogen of the sulfuric
acid and is protonated while the oxygen in the sulfuric acid is negatively
charged.
After that, the oxygen in the hydroxyl group of the salicylic acid attacks one
carbon of a carbonyl group when it is liberated.
The deprotonated sulfuric acid attacks the protonated oxygen and recovers the
hydrogen and the product is obtained.
For the aspirin synthesis process, the amount of salicylic acid used was 2,020 g
according to the weight on the balance. Thanks to the synthesis process
between salicylic acid and acetic anhydride in an H2SO4 concentrate, the first
phase of our aspirin could be obtained, which was called crude aspirin in which
a loss of mass could already be witnessed, this loss can be produced by the
retention of some product in the equipment used for the synthesis. Then, we
worked with the first crystallization of the aspirin when it was cooled, but not
before taking a sample of our raw aspirin, in order to make the FeCl3 test.
This is due to a possible loss in the equipment and the filtration that was
performed because the recrystallization is performed to purify the product
because that loss contained impurities that were retained inside the crystals
during the filtration process and then were eliminated by the recrystallization.
This can be confirmed by the FeCl3 test.
In this practice, the ferric chloride technique is used to identify the product
formed and determine its purity since through this test it is possible to
determine the presence of phenol groups. The first test carried out was on a
salicylic acid sample, obtaining a purple color due to this compound containing
phenols. Then the crude aspirin test obtained in the first crystallization was
carried out, obtaining a violet color that indicated the presence of salicylic acid
(reagent used in the synthesis) for which it was necessary to perform
recrystallization of the product, also during this process it was done another
test in the mother liquor and, as expected, the test was also positive for the
presence of phenols. The test carried out after recrystallization presented a
yellow color that showed us that the decision to carry out the second
recrystallization to purify our product was correct, however, it is avoidable
thinking that despite having performed recrystallization there is a qualitatively
notable difference possibly due to the fact that there are still remnants of
salicylic acid in the recrystallized product.
Last but not least, we must highlight the participation of Infrared Spectroscopy,
where IR spectra allow us to determine the presence or absence of certain
functional groups in a compound. For this practice we took a sample of our
pure sample in order to obtain the following results:
Figure 3: IR of Aspirin
As we observe in the image, we see that there is the presence of our compound
which means that the process of synthesis and recrystallization of our product
has been carried out successfully.
4. Taking into account the melting point value and the FeCl3 test, can you assure
that your compound is pure? Why?
For this experiment, the melting point could not be obtained because the
melting point as such was not found during the virtual session of this practical.
However, we did perform the FeCl3 test, and additionally, we worked with the
Infrared Spectroscopy where the results obtained during this practice show that
there is a large amount of acetylsalicylic acid (aspirin) both in the FeCl3 test
because the color obtained in the pure sample was yellow while in the infrared
spectroscopy shows a clear presence of our main product aspirin.
FINAL EVALUATION:
1. What is the purpose/consequences of recrystallization?
The attractive forces that hold solute molecules to other solute molecules
(usually Van der Waals interactions) are overcome during the recrystallization
process. Recrystallization does not involve breaking any chemical bonds.
Which is the most adequate solvent for this purpose (in general)
The most suitable solvent is the one with the largest difference between hot
solubility and cold solubility, with this property, more product will be recovered
from recrystallization.
In other words, the criteria used to choose the most suitable solvent:
1.- Find a solvent with a high-temperature coefficient: The solvent should not
dissolve the compound at low temperatures (that includes room
temperature), but should dissolve the compound at high temperatures.
2.- Use a solvent that dissolves impurities easily or not at all. If the solvent
dissolves the impurities easily, the impurities will not be trapped in the
developing crystal lattice but will remain dissolved in the solvent.
3.- Ensure that the solvent does not react with the solute.
The information we obtain from the FeCl3 assay is helpful because it helps us to
determine the presence of phenols in a given sample or compound. We can
know that phenols are present due to the formation of a red, blue, green, or
violet coloration. It is also possible to determine quantitatively which
compound was obtained.
We can slightly observe some impurities by recrystallizing aspirin, and its colors
vary from yellow to orange. In addition, the crude aspirin can be concluded to
have a purple coloration, which indicates the presence of agents in the product
obtained.
In addition, It is important to wash the aspirin product with cold water because
this way we prevent the crystals formed during the crystallization process from
dissolving, and at the same time we eliminate the possible impurities present
that are soluble in water.
❖REFERENCES
● Acetylsalicylic Acid; MSDS No. 50-78-2; Sigma-Aldrich Inc. 3050 Spruce Street ST.
LOUIS MO 63103 UNITED STATES November 20, 2020.
● Calderon, Greece. (2018). Esters. Retrieved May 27, 2021, from Euston96:
https://www.euston96.com/esteres/
● Synthesis of Aspirin (Experiment). (2020, June 29). Retrieved June 1, 2021, from
https://chem.libretexts.org/@go/page/61311
● Olguín, S. 1996. Manual de prácticas de química orgánica I. Universidad
Autónoma Metropolitana-Iztapalapa. México.
● Reusch, W.H. 1979. Química Orgánica. McGraw-Hill, México.
● Koester, M. C. An Overview Of The Physiology And Pharmacology Of Aspirin And
Nonsteroidal Anti-Inflammatory Drugs. J. Athl. Train. 1993, 28 (3), 252–259.