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Oxida&on of Borneol Experiment
Chem 336: Experimental Organic Chemistry II
Experiment #3 [followup discussion]
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NMR analysis in the oxida&on of borneol to camphor
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NMR of SM: comparison with authen6c borneol
chem377_borneol_sm_001001r.esp
4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
Nor
mal
ized
Inte
nsity
11.142.241.321.232.981.131.060.311.00
which proton in borneol is expected
to be far downfield, i.e. at 4.0?
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NMR analysis of SM: small contaminant at 3.6 ppm
chem377_borneol_sm_001001r.esp
4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
Nor
mal
ized
Inte
nsity
11.142.241.321.232.981.131.060.311.00
which proton in isoborneol is expected
to be far downfield, i.e. at 3.6?
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NMR data for your class sec&on
(please print and aCach to your informal report)
not much NMR assignment this experiment for your lab report
(given how complicated the NMR is)
things to discuss in your report: a) assignment of the downeld
diastereotopic CH2 group
b)does the integra&on of the signals add up? c) presence of
upeld 3 x 3H in the upeld region
d)purity? presence of SM in product? e)Trace of solvent (from aq
workup), what is it??
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1H-NMR: Sec6on 4: Dr. Amagata
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1H-NMR: Sec6on 5: Vi-Anh Vu
? ?
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1H-NMR: Sec6on 6: Michel Lau
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1H-NMR: Thursday Sec6on: Jason Ji
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chem377_expt3_camphor_lisas_section_001001r.esp
4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)
0
0.25
0.50
0.75
No
rma
liz
ed
In
ten
sit
y
2.952.972.101.491.021.071.121.00
ques&ons: [1] what parts of spectrum are expected to be
downeld? (to the leU) upeld ? (to the right) [2] any trace
contamina&on with borneol SM?
NMR analysis of product (comparison with Aldrich)
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