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Borneol Oxidation Followup Style 1
Citation preview
Oxida&on of Borneol Experiment
Chem 336: Experimental Organic Chemistry II
Experiment #3 [followup discussion]
NMR analysis in the oxida&on of borneol to camphor
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?
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?
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??
1H-NMR: Sec6on 4: Dr. Amagata
1H-NMR: Sec6on 5: Vi-Anh Vu
? ?
1H-NMR: Sec6on 6: Michel Lau
1H-NMR: Thursday Sec6on: Jason Ji
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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