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George Pappas
Introduction/ Background
loss of electrons. Hence, when an element loses electrons during a reaction, the reaction is
considered to be an oxidation reaction. In organic chemistry, the focus of the oxidation reaction
turns to the gain of bonds, specifically between carbon and oxygen atoms. In other words, when
carbon gains a bond with oxygen, it illustrates that an oxidation reaction has taken place. In
effort for carbon to acquire bonds with an oxygen, a particular oxidizing agent might be used.
The number of bonds formed between a carbon atom and an oxygen atom depends on the
strength of the oxidizing agent. For example, in effort to oxidize an alcohol to a carboxylic acid,
one would use a strong oxidizing agent. This reaction would result with a carbon with 3 bonds to
oxygen atoms. If an alcohol was oxidized with a weaker oxidizing agent, an aldehyde would
possibly form. This includes a carbon atom with 2 bonds to an oxygen atom.
Over the years, the department of chemistry has been looking for an efficient, hazard free,
ozone friendly oxidizing agent. There are plenty of oxidizing agents that are effective when used
in an experiment. However, these reagents are very harmful to, not only the people performing
the lab, but also the atmosphere around them. In order for a safe, toxic free lab, more
environment-friendly reagents were used traditional oxidizing agents. The result of the
experiment, however, was not satisfying due to the lack of effectiveness of the agents. Although
the struggle continued for years, these incidents finally ended with the establishment of a reagent
that was both hazardless and efficient Oxone. This powerful agent allows chemists to perform
experiments without the fear of handling a solution that can damage their skin or mucous
membranes from inhalation. In addition, the chemical also provides promising results which
further clarifies it as a better alternative from the traditional chemicals used before.
In this particular experiment, Oxone is used as the oxidizing agent in replacement of the
traditional chemical, bleach. Although bleach is a safe oxidation method, the agent has not
brought pleasing results. With that said, Oxone stands as the better agent as it is less toxic, ozone
friendly, and effective when pertaining to the actual procedure. The salts in the solution are
harmless to the human body. This particular agent is also cheaper and accessible in comparison
to bleach.
In this experiment, Borneol, standing as a secondary alcohol, will be oxidized by the new
and improved reagent Oxone, to further become Camphor a ketone. Other than the aqueous
layer that is eventually removed/separated from the organic layer, there were no other side
Figure 1:
Experimental Section
Set up steam Add 200 mg of Add 1ml of Weigh .5g Oxone and
bath for later Bornoel to 10ml ethyl acetate, 50mg of NaCl and add
removal of vial stir. to mixture along with
solvent 1 ml deionized water
Add 3ml of Preform another TLC Perform TLC with
Meanwhile,
with organic layer.organic stir
layer using
deionized water reaction for 30
and a tip full of 9ml of hexane and
(stir for another 15min
min using
1mlethyl
if the reaction is still stir as
acetate
Sodium Bisulfate plate.
using a spatula not complete solvent
Decant organic
layer to a
Wash drying Extract
previously weight Washaqueous
organiclayer
agent off with withlayer
Erlenmeyer flask ethylwith
acetate and
brine
1ml ethyl acetate combine
with boiling stone with
and dry organic
with
in it layers into 4vial
MgSO
Remove (5min)
flask
Place flask in Find percent
from steam when yield
steam bath Use compressed and melting
completely point.
(OVER hot air to evaporate Get an IR
evaporated
water) solvent spectrum
Table of Chemicals
Borneol C10H18O
MM: 154g/mol
MP: 208C
BP: 213C
Oxone KHSO4
MM: 152.2g/mol
MP: Decomposes
BP: Decomposes
Hexane C6H14
MM: 86.18g/mol
BP: 68C
Magnesium Sulfate MgSO4
MM: 120.366g/mol
MP:1124C
Results
Calculation of Rf Value:
Discussion
The theoretical melting point for Camphor stands at 175C. The actual melting point was
180C. This result magnifies that the overall procedure was performed successfully, providing
satisfying values. There might have been a slight amount of impurities in the final product
causing the melting point to be slightly higher. Otherwise the experimental melting point was
very close to the desired value. The experiment concluded with a percent yield of 101%. This
value illustrates that there must have been an error that occurred somewhere during the
experiment. The inaccuracy with the scale most likely caused the high percent yield. Inaccurate
measurements during the beginning of the lab acts as a possible error causing such a high yield.
The IR spectrum in Figure 1 above illustrates a peak near 1700cm-1. A ketone lies within
the range of 1750-1680cm-1. This information further clarifies that a ketone is present in the IR
spectrum. There are two other peaks that lie between 3000cm-1 and 3500cm-1. These peaks
signify that alkanes are also present one more downfield than the other due to its position in the
downfield near 3500cm-1 to signify its alcohol. Its other peaks would have lied in between
3000cm-1 and 3400cm-1 to clarify the methyl groups present in the compound.
Thin layer chromatography acts as a significant factor in the oxidation of Borneol. The
procedure allows one to determine whether or not borneol has successfully reacted into camphor.
After performing a TLC, if two dots are present on the TLC plate, then that means that he
reaction is not completed and both Borneol and Camphor are showing up. In effort to obtain a
completed reaction, one must achieve a TLC plate with only one dot on it. This further indicates
that the reaction is completed. The IR spectrum also acts as a significant factor as it concludes
that the final product obtained is the desired camphor. By interpreting the IR spectrum one can
find the functional groups present in Camphor to further determine whether or not Camphor is
the final product obtained. If functional groups from Borneol are still present in the IR spectrum,
then it is understood that the reaction was not complete, further concluding that the final product
Conclusion
With the help of a less hazardous, more environment-friendly oxidizing agent Oxone,
the oxidation of Borneol was a success as the experiment concluded with a ketone Camphor.
This reflects the theory of organic oxidation as it signifies oxidation by gaining more bonds
higher percent yield, does not support that the methods used in the experiment were
unsuccessful. However, with the experimental melting point at 180C similar to the literature
melting point, the overall procedure exhibited success. This theory goes beyond the laboratory,
as well. Any cleaning product used in todays time acts as an oxidizing agent ready for its
References