Imaan Hussain

Bence Zakota and Christian Ward

George Pappas

Green Oxidation of Borneol to Camphor with Oxone

Introduction/ Background

A general oxidation-reduction reaction involves the transfer of electrons. Oxidation, is the

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

reactions that took place during the experiment.

 Mechanism

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

Take out magnetic

Test aqueous layer stir bar with forceps Take aqueous
Rinse with 1ml
with starch iodine layer out using
of ethyl acetate
paper pipet
backand
intotransfer
the
tomixture.
5ml vial

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

Ketone (Camphor) C10H17O

MM: 152.23g/mol
MP: 175C
BP: 209C

Oxone KHSO4
MM: 152.2g/mol
MP: Decomposes
BP: Decomposes

Sodium Bisulfate NaHSO4

MM: 120.06g/mol
MP: 58.5C
BP: 315C

Ethyl Acetate C4H8O2

MM: 88.11 g/mol
MP: -83.6C
BP: 77.1C

Hexane C6H14
MM: 86.18g/mol
BP: 68C
Magnesium Sulfate MgSO4
MM: 120.366g/mol
MP:1124C

Results

Physical properties of Camphor

Melting Point 180 - 184C

Appearance White/clear film with a strong odor
Weight 0.2g

Calculation for percent Yield

Preweighed Flask: 85.6g

Flask with Camphor: 85.8g

Mass of Camphor: 85.8g - 85.6g = 0.2g

.2g of Borneol (1 mol Borneol/ 154g Borneol) = .0013 moles

0013 moles (152.23g Camphor/ 1 mol Camphor) = .1979g

Percent Yield: (19g/.1979g) x 100 = 101%

Calculation of Rf Value:

Distance traveled by compound = Rf

Distance traveled by solvent

0.9cm/5.3cm = Rf value for Borneol = 0.17

2.1cm/5.3cm = Rf value for Camphor = 0.40

Figure 1: IR spectrum for Camphor

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

molecular structure. In comparison, Borneols IR spectrum would have included a peak

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

is a mixture of Borneol and camphor.

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

between carbon and oxygen.

 The trouble with the scale, causing inaccurate measurements and further leading to a

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

oxidation reaction, pertaining to a tough stain or a dirty floor.

References

Weldegirma, Solomon. Experimental Organic Chemistry. Tampa, Fl, Department of

Chemistry, 2016. Print.

Applications of Redox Reactions in Real Life | Oxidation Number. Chemistry. Byjus

Classes, 22 Aug. 2016. Web. 08 Feb. 2017.

Libretexts. "16.1: Oxidation and Reduction of Organic Compounds - an Overview.

"Chemistry LibreTexts. Libretexts, 21 July 2016. Web. 08 Feb. 2017.