Oxidation of Borneol to Camphor

Student Guidelines for Green Oxidation of Borneol to Camphor
Spring 2017 – 150 pts
Title, Name, TA Name, Section, Date.
A reminder that all chemical structures should either be hand drawn or generated in ChemBioDraw (or similar
software) in original form. Graphics copied from the manual, the internet, or any other source will result in a zero
for the report.
15 pts Quality of Writing and Mechanics of Report (15 pts)
Spelling and Grammar ___/5 pts
Scientific style (3rd person past tense) throughout ____/5 pts
Results/Discussion/Conclusion: Well organized, clear and concise ____/5 pts
13 pts Purpose and Reaction Scheme – follow directions in Appendix A. Include labels on all chiral carbons as
R or S for starting material and product. For students using ChemDraw note it is very helpful to know
there is a templete for bicyclics
12 pts Mechanism: Mechanism from page 80 of the manual and lecture powerpoint should be redrawn using
borneol as the starting material and camphor as the product. Discussion should include which atoms are
oxidized and which are reduced and discussion of the catalyst.
5 pts Procedure: Reference the procedure followed and state any significant deviations or experimental details
that would impact the outcome of the experiment. Describe the sublimation apparatus used.
5 pts Reagents Table – Include MW, grams used, and associated mmols for 1S-borneol, Oxone, potassium
peroxymonosulfate (amount in Oxone used), NaCl, and theoretical amount of camphor expected.
50 pts Results and Observations: Use table format where appropriate. Include observations for the reaction
AND sublimation. Present mass of crude product before and after desiccator drying, masses associated
with the sublimation and corresponding % yields. Document what material was used for characterizations:
melting point (compared to literature), IR (attach and label all significant peaks including methylene
chloride) prepare of table of key stretches for the camphor product (and starting material if present)
H NMR – Refer to the NMRs and discussions given on p. 81 of the manual where it states “it is not
necessary to identify chemical shift, splitting patterns, or coupling constants for every single proton”. On
the spectrum identify all peaks that distinguish between borneol (Ha, Hb…)and camphor (Hb’, using
primes). Label any solvent peaks remaining. Calculate the purity of camphor based on the integration of
the methyl singlets. Show your calculations. Summarize the results in a table giving ONLY the chemical
shifts and integrations used for determining the % purity. Include any solvent peak also. The assigned
structures below will be helpful in using your OWN spectrum.
40 pts Conclusion and Discussion. The conclusion should summarize the success of the reaction performed
based on yield, purity, and percent conversion. Explain how each characterization (mpt, IR, and NMR)
supported structure and purity. Discuss whether sublimation was an effective way to purify the product.
And finally address three Green Chemistry Principles exemplified in the reaction. Which green chemistry
principle was not meet with respect to Oxone as a reagent?
Additional Questions
7 pts Terpenes – Find a terpene natural product of interest to you with 15 carbons (sesquiterpene, diterpenes,
etc..) or more. Draw its structure and circle EACH isoprene unit present. Identify where it can be found in
nature and any interesting biological properties known. Reference your source(s)
3 pts: Calculate the three J values for the ddd for the methine of borneol given on page 82 of the manual.