03results and Discussion For Aspirin

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Results and Discussions:

The first part of the experiment
was the preparation of aspirin.
Acetylsalicylic acid or Aspirin was
produced by salicylic acid reacted with an
excess of acetic anhydride, with a small
amount of concentrated sulphuric acid as
the catalyst [3]. The reaction behind the
prepared aspirin was nucleophilic acyl
substitution. Nucleophilic acyl
substitution happens when the
initially formed intermediate expels
one of the substitutes originally
bonded to the carbonyl carbon
leading to the formation of a new
carbonyl compound [7]. The salicylic
acid molecule actually has two functional
groups attached to it, an acid and an
alcohol. The concentrated sulphuric acid
protonated the carbonyl oxygen atom of
the acetic anhydride thus made it
susceptible to nucleophilic attacks. The
salicylic acid with nucleophilic group
attacked the electron deficient acetic
anhydride. The hydroxyl group attached to
the electrophilic carbon removed the
hydrogen as proton: donating the electron
to form a double bond (C=O). The
hydroxyl group of salicylic acid was then
converted into an acetyl group. [7].

The purpose of adding water drop-
wise was to make the solution cloudy,
making the excess anhydride undergo
hydrolysis, a chemical process whereby a
bond in a molecule is broken by its
reaction with water [6]. The presence of
precipitates means that one of the C-O
bonds of acetic anhydride is hydrolyzed,
releasing two acetic acid molecules. Since
acetylsalicylic is insoluble in ice-cold
water, it was used to facilitate the
crystallization. The ice-cold water will
further reduce the solubility of the product
in the water and this would increase the
percent yield [9]. After drying, the end
product was a white fine powder. The
prepared acetylsalicylic weighs 2.10g. The
computed theoretical yield was 2.83g. The
percentage yield was obtained by getting
the ratio of actual yield and theoretical
yield multiplied by 100, thus the
percentage yield obtained was 74%. It is
possible that the 26% loss was due to the
loss of product while transferring,
incomplete conversion of the reactants,
and prolonged drying.

Ferric chloride was used to
determine the presence of salicylic acid.
Ferric chloride reacts with the phenol
present in the salicylic acid.
Acetylsalicylic together with benzoic acid,
and benzyl alcohol does not contain
phenol group, so it must give a negative
result, which is the violet coloration of the
solution [8]. In the prepared aspirin, a light
violet solution was observed. Benzoic
acid, benzyl alcohol, and control solution
gave negative results, while commercially
available ASA and prepared ASA turned
into light violet solution. This means that
small amount of salicylic acid is still
present in the solution.

Table1: Data of Ferric Chloride Test for the
Presence of Salicylic Acid

Test Tube Color Noted
A. Salicylic Acid Violet solution
B. Commercially
available ASA (Bayer)
Cloudy solution
C. Prepared ASA Light violet
solution
D. Benzoic Acid Clear solution
E. Benzyl Alcohol Yellow solution
with oil globules
F. Control Clear solution

Figure1. Results of the Ferric Chloride
Test for Salicylic Acid.

In the starch test, only the
prepared acetylsalicylic acid gave a clear
solution. This test proves the existence of
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starch in the commercially available
acetylsalicylic acid.

Table2: Data of Starch Test Results.
Test Tube Color Noted
A. Prepared ASA Cloudy solution
B. Commercially
available ASA
Light purple
solution
C. Control Cloudy violet
solution

Figure2. Results of the Starch Test.

[3] California State University Stanislaus.
(n.d.). The Synthesis of Aspirin. Retrived
from
http://wwwchem.csustan.edu/consumer/as
pirincons/aspirincons.htm

[7] Academia. (n.d.). Retrieved from
http://www.academia.edu/4728996/Acetyl
salicylic_Acid_Aspirin_Synthesis

[6] Brown, W., & Poon, T.
(2014).Introduction to organic chemistry
(p. 501). Hoboken, NJ: John Wiley and
Sons.

[8] Laney College. (n.d.). Retrieved from
http://www.laney.edu/wp/cheli-
fossum/files/2012/01/8-Synthesis-of-
Aspirin.pdf

[9] Xavier University of Louisiana. (n.d.).
Retrieved from
http://www.xula.edu/chemistry/documents
/orgleclab/24AspirinN.pdf

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