Experiment 3: POST-LAB REPORT 1
Experiment 3: Green Oxidation of Borneol to Camphor with Oxone
Claudia Zamora Cisnero
T.A. Ning Shen
University of South Florida: CHM2211L.903
January 27, 2021
POST-LAB REPORT 2
Introduction
The purpose of this experiment was to synthesize camphor from the reaction between
borneol and the green oxidation agent, Oxone. There are multiple oxidation reactions in organic
chemistry, many of which allow for the formation of aldehydes, ketones, and/or carboxylic acids.
Such oxidation reactions heavily depend on the structure of the alcohol substrate. However, the
oxidations agent employed also plays an essential role in the development of the reaction.
Oxidating compounds such as pyridinium chlorochromate (PCC) and chromic acid (H2CrO4) can
turn alcohols into carboxylic acids and ketones efficiently. PCC in particular is more selective
and can lead to the formation of an aldehyde from a primary alcohol. These compounds have
been utilized in oxidation chemistry traditionally, nonetheless, they are toxic and dangerous for
the environment. Common chromium-based agents are known to be corrosive, carcinogenic, and
harmful to mucous membranes. Moreover, the byproducts that form from oxidation reactions,
using these toxic compounds in specific, are hazardous and represent a disposal issue.1
Other similar agents have been employed to reduce these problems, but they have not
been entirely successful, as the resulting yield is significantly low. Oxone, on the other hand, is a
safe green alternative that is gaining popularity in the field, as the salts produced in the oxidation
process are benign and the environmental and health hazards/risks are very low. Oxone is a triple
salt (2KHSO5-KHSO4-K2SO4) that uses potassium peroxymonosulfate (KHSO5) as the main
oxidating agent. Under certain conditions, Oxone oxidizes chloride ions into molecular chlorine.
As such, hypochlorous acid (HOCl) already present in the reaction mixture is most likely the
compound that oxidizes the alcohol group un borneol.1
Mechanism
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Figure 1. Mechanism for the Green Oxidation of Borneol to Camphor Using Oxone
Side Reaction
Figure 2. Side Reaction for the Green Oxidation of Borneol to Camphor Using Oxone
Experiment Procedure
Part A:
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1) Round Bottom Vial 2) Reaction Mixture 3) Reaction
Complete
+ magnetic stir bar + take TLC
+ confirm reaction is
complete using TLC
+ 0.2 g borneol
+ use iodine chamber
+ add 30 mL deionized
+ 1.0 mL ethyl acetate water
+ stir for 30 minutes
+ use spatula to add
+ 0.5 g oxone sodium bisulfite to
+ use TLC reduce trace oxone
+ 50 mg NaCl
+ if there is still borneol, + test the aqueous layer
allow 15 minutes for using starch iodine
further reaction paper
+ 1.0 mL deionized water
+ add more sodium
bisulfite if paper turns blue
+ remove magnetic stir
bar
+ add 1 mL of ethyl acetate,
shake and let it stand for 2
minutes
Figure 3. Procedure for the Green Oxidation of Borneol to Camphor Using Oxone (Part A)
Part B:
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2) Final Product 3) Analysis of Camphor
1) Separation
Preparation Product
+ using pipet, remove + obtain mass
aqueous layer, transfer to + decant prganic layer
5 mL conical vial. into pre-weighed 25
mL erlenmeyer flask
with boiling stone
+ calculate percent yield
+ add 1 mL of ethyl acetate
to aqueous laye, shake
mixture and let it stand for 2 + wash magnesium
minutes sulfate using 1 mL
ethyl acetate + determine melting
point
+ extract aqueous layer and + steam bath the organic
combine the organic layers layer and add a gentle + obtain 1HNMR and
in the conical vial stream of compressed air 13
C NMR
+ add brine solution
ot the vial + camphor should form as + obtain IR spectrum
solid residue within flask
+ shake and let it stand
for 2 minutes
+ remove brine layer
+ dry organic layer with
magnesium sulfate, 2-3
spatula scoops
+ let it rest for 5
minutes
Figure 4. Procedure for the Green Oxidation of Borneol to Camphor Using Oxone (Part B)
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Chemicals Used
BORNEOL
Physical and Chemical Properties
Structure formula molar mass boiling point
C 10 H 18 O 154.3 g/mol 210 °C
melting point density Hazards
Flammable
209 °C 0.99 g/mL Irritant
ETHYL ACETATE
Physical and Chemical Properties
Structure formula molar mass boiling point
C 4 H 8 O2 88.1 g/mol 77 °C
melting point density Hazards
Highly flammable
-83.6 °C 0.902 g/mL Causes eye irritation
May cause dizziness
or drowsiness
CAMPHOR
Physical and Chemical Properties
Structure formula molar mass boiling point
C 10 H 16 O 152.2 g/mol 175 °C
melting point density Hazards
179-182 °C 0.992 g/mL Flammable
Harmful if
swallowed
Harmful if inhaled
May cause damage
to organs
OXONE
Physical and Chemical Properties
Structure formula molar mass boiling point
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KH SO 5 152.2 g/mol N/A
melting point density Hazards
- Hazardous if inhaled
1.5 g/mL Toxic if ingested
Skin and eye irritant
SODIUM CHLORIDE
Physical and Chemical Properties
Structure formula molar mass boiling point
NaCl 58.4 g/mol 1465 °C
melting point density Hazards
-95.3 °C 2.16 g/mL Irritant
HEXANE
Physical and Chemical Properties
Structure formula molar mass boiling point
C 6 H 14 86.2 g/mol 68.7 °C
melting point density Hazards
0.66 g/mL
-95.3 °C Highly flammable
Fatal if swallowed
Skin irritant
SODIUM BISULFATE
Physical and Chemical Properties
Structure formula molar mass boiling point
NaHS O 3 104.1 g/mol 104 °C
melting point density Hazards
Decomposes 1.34 g/mL Harmful if swallowed
MAGNESIUM SULFATE
Physical and Chemical Properties
Structure formula molar mass boiling point
MgS O 4 120.4 g/mol -
melting point density Hazards
1124 °C 2.66g/mL Harmful if swallowed
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Irritant
Hazardous if inhaled
Table 1. Compounds Used During the Green Oxidation of Borneol to Camphor Using Oxone
Experiment Results
TLC: Distance travelled by the solvent 3.5cm
TLC: Distance travelled by the Borneol 1.5 cm
TLC: Distance travelled by the product 2.2cm
Melting point of the desired product 172 °C
Mass of the final desired product 0.095 g
Percent Yield 94%
Table 2. Results of the Green Oxidation of Borneol to Camphor Using Oxone
Percent Yield Calculations:
Limiting reagent is C 10 H 18 O (borneol)
1 mol C 10 H 18 O 1 mol C 10 H 16 O 152.2 g/mol
0.2 gC 10 H 18 O× × × =0.197 g C 10 H 16 O
154.3 g /mol 1 mol C 10 H 18 O 1mol C 10 H 16 O
Theoretical Yield for the product is 0.21 g
Actual Yield 0.197 g
× 100 %= ×100 %=94 %
Theoretical Yield 0.0 21 g
Figure 5. 1H NMR spectrum of the final desired product
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Figure 6. 1H NMR spectrum of the final desired product
Figure 7. 1H NMR spectrum of camphor.
Discussion
In this experiment, the final product can be accurately identified using melting point. The
literature value for the melting point of camphor is 175 °C, while the obtained value for the
collected product is 172 °C. Both melting point values are very close, demonstrating that the
final product is indeed camphor. Nonetheless, it is important to acknowledge that the small
difference (3 °C) between the two values might account for impurities in the final product,
POST-LAB REPORT 10
according to the melting point depression theory. Random and/or systematic errors throughout
the procedure or the melting point analysis could have also lowed the melting point of the final
product. The percent yield of the product was determined to be 94%, which indicates that the
overall procedure was performed efficiently and 94% of reagents (borneol and Oxone) turned
into the final product (camphor).
The obtained substance was analyzed using IR and 1HNMR spectroscopy also. The IR
spectrum displayed a prominent peak around 1750 cm-1, which indicates the presence of a
carbonyl group. This peak certainly accounts for the ketone functional group found in the
structure of camphor. Furthermore, the IR spectrum reveals a sharp peak around 3000 cm-1,
which is characteristic of sp3 C-H bonds in a compound, and in this case, it could represent the
three methyl groups and other bonds observed in camphor. As excepted, the IR spectrum does
not display any other significant peaks that could represent other functional groups. Meanwhile,
the 1HNMR spectrum shows two peaks around 0.9 ppm, a usual chemical shift for methyl
groups. As previously discussed, camphor contains three methyl groups in its structure, but two
of these are chemically equivalent, resulting in only two signals. TLC played an essential role in
this experiment, as it ensured that borneol was not present throughout the synthesis of camphor.
As such, the use of TLC reduced error and allowed for an efficient reaction.
Conclusion
The main objective of this experiment was to synthesize camphor using borneol and the
green oxidating agent Oxone. After performing the reaction, four indicators were employed to
identify the final product. First, the compound’s melting point was obtained and compared to the
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literature value. The product’s melting point was determined to be 172 °C, while the literature
value for camphor is 175 °C. It was concluded that such a similarity must indicate that the final
product was indeed camphor and that the 3°C difference was most likely caused by impurities. In
addition, the percent yield of the product was calculated to be 94%, which suggests that the
overall synthesis was efficient. Finally, IR and 1HNMR spectroscopy were utilized for further
analysis of the product. The IR spectrum showed peaks that demonstrated the presence of a
carbonyl and sp3 C-H bonds, which accounts for the ketone functional group and the methyl
groups in the structure of camphor. The 1HNMR spectrum, as excepted, displayed two peaks that
indicated the presence of one unique methyl group and two equivalent methyl groups. The
utilization of TLC ensured a quality synthesis and a successful reaction.
Oxone is widely utilized as a greener alternative to other oxidating agents. For example,
Oxone can be used to sanitize swimming pools and minimize the amount of chlorine that is
utilized. This is because Oxone can maintain the water clear while the chlorine purifies the water,
so a lesser amount of chlorine is needed. However, in certain conditions, toxic byproducts can
result from this treatment.2 Overall, this experiment accomplished what it set out to do. The
synthesis proceeded efficiently and the final product was identified using different methods. As
such, it is fair to conclude that the synthesis of camphor via green oxidation was successful.
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References
[1] Weldegirma, S. (2020) Experiment 3: Green Oxidation of Borneol to Camphor with Oxone.
Experimental Organic Chemistry. pg. 88-91.
[2] Wikipedia contributors. (2021, January 14). Potassium peroxymonosulfate. In Wikipedia, The
Free Encyclopedia. Retrieved 03:31, January 28, 2021,
from https://en.wikipedia.org/w/index.php?
title=Potassium_peroxymonosulfate&oldid=1000224881
[3] Borneol. National Center for Biotechnology Information. PubChem Compound Database.
U.S. National Library of Medicine.
[4] Ethyl Acetate. National Center for Biotechnology Information. PubChem Compound
Database. U.S. National Library of Medicine.
[5] Camphor. National Center for Biotechnology Information. PubChem Compound Database.
U.S. National Library of Medicine.
[6] Oxone. National Center for Biotechnology Information. PubChem Compound Database. U.S.
National Library of Medicine.
[7] Sodium Chloride. National Center for Biotechnology Information. PubChem Compound
Database. U.S. National Library of Medicine.
[8] Hexane. National Center for Biotechnology Information. PubChem Compound Database.
U.S. National Library of Medicine.
[9] Sodium Bisulfite. National Center for Biotechnology Information. PubChem Compound
Database. U.S. National Library of Medicine.
[10] Magnesium Sulfate. National Center for Biotechnology Information. PubChem Compound
Database. U.S. National Library of Medicine.
