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Kristy (Eun) Choi 309B

W1500 Section 3
April 22, 2014
General Chemistry Laboratory Experiment #9 Report
The purpose proposed at the beginning of the experiment was to synthesize aspirin
(acetylsalicylic acid) using salicylic acid and acetic anhydride, and to determine the purity of the
resultant aspirin sample by titrating it with NaOH and HCl, using melting-point analysis with the
DigiMelt, and carrying out the phenol test. This experiment was especially difficult for our group
because we literally made every single mistake possible throughout the course of the procedure, but
in the end we were able to obtain aspirin crystals and though of questionable accuracy
analyzable results.
My partners and I were only able to obtain a 0.804 .003g yield of aspirin, a mere 30.8
.1% yield from the theoretical yield of 2.609 .001g. However, there were a variety of procedural
errors that contributed to our poor results. Despite the fact that we there were very small amounts of
salicylic acid residue on the spatula and side of the Erlenmeyer flask (which would have resulted in
a slightly lower yield), we originally had significant crystal formation while cooling the solution in
the ice water bath. But then we forgot to completely dissolve the aspirin in ethanol before adding
the 35mL of water. This resulted in white precipitate floating in solution that would not dissolve, so
we were told to decant some of the water and re-dissolve the aspirin in more ethanol. We obviously
lost some product as we were decanting, and then some more as we re-filtered the solution through
the vacuum filtration apparatus. We also forgot to save the filtrate from the second round of
filtration to add to our experimental yield because we were pressed for time. These sources of error
all contributed to the low experimental yield of aspirin.
The process of re-dissolving the aspirin in more ethanol and adding water once again to
continue with the experiment meant that the aspirin was not going to be very pure, especially since

we did not quite get the heated solution in the Erlenmeyer flask to room temperature as we put it
again into the ice bath. This meant that the aspirin crystals would trap impurities upon formation,
and yielded a low percent purity value of 35.6 .8%. But contrary to our very poor percent purity,
we obtained a fairly reasonable temperature range for the melting point: 136.0C ~ 139.3C. This
was not terribly off from the true melting point range, which was 133~135C (we were expecting
the discrepancy to be much more prominent), though still not accurate. Our higher result makes
sense due to the impurities trapped in the aspirin, which would pull up the melting point.
We also made another very serious mistake: after titrating our aspirin sample with NaOH,
we accidentally threw out the titrated solution before we could back-titrate it with HCl and obtain
the pKa. We were all under considerable stress and pressure because our experiment seemed to be
falling apart and we were also one of the slowest groups, so I discarded the solution while cleaning
up before I could think twice. As it was too late, we borrowed another groups data for the pKa,
which was 3.74. This was not the most accurate answer, as the true pKa of aspirin at 25C is 3.5,
but we appreciated the fact that the other group was generous enough to help us out. We suspect
that our results would probably have been similar in terms of accuracy. The phenol test yielded
accurate results, however, as the salicylic acid solution took on a deep purple shade after adding 10
drops of FeCl3 with no reaction in the aspirin solution.
All in all, my partners and I struggled to follow the experimental procedures accurately and
efficiently for this experiment. Had we not committed that one fatal mistake of failing to dissolve
the aspirin in ethanol before adding water, I feel as though the experiment would have run perfectly
with a much smaller margin of error as losing some of the aspirin product would have been
inevitable. That one mistake set off a chain reaction that made everything go awry. But as we have
learned our lesson, we will take care to peruse the instructions before jumping into the next (and
last!) experiment.

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