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Trondheim
Institutt for kjemi
KJ 2022/TKJ 4115
chemistry
KJ 2022/ TKJ 4115 Spectroscopic methods in organic chemistry, Examination June 2. 2006 1
Exercise 1 ( 50 points)
• Find the structure of the compound who´s spectra are shown i Figure 1.
Figure 1
KJ 2022/ TKJ 4115 Spectroscopic methods in organic chemistry, Examination June 2. 2006 2
Exercise 2 (20 points)
• The IR and 1H NMR spectra for an unknown compound with the formula
C9H10O are given in Figure 2. Find the structure.
Figure 2
KJ 2022/ TKJ 4115 Spectroscopic methods in organic chemistry, Examination June 2. 2006 3
Exercise 3 (20 points)
a)
• Interpret the COSY (1H-1H correlated) and HSQC (1H-13C correlated) spectra
for 5-bromo-2-methyl-1-pentene which are shown in Figures 3a and 3b,
respectively. (A peak at 143 ppm in the 13C spectrum is omitted).
Br
Figure 3a
KJ 2022/ TKJ 4115 Spectroscopic methods in organic chemistry, Examination June 2. 2006 4
HSQC
Figure 3b
b)
• Figure 4 shows the mass spectrum of a secondary amine. Explain the peaks
with m/z-values.
Figure 4
KJ 2022/ TKJ 4115 Spectroscopic methods in organic chemistry, Examination June 2. 2006 5
c)
• Draw the ionic structures and annotate the five possible fragmentations a-e.
• The unsaturated ketones below have the following lmaks values: 254, 239, 324,
249, 244 og 407 nm. Assign the right lmaks value to the respective ketone by
using Table 1.6 fra Williamson & Fleming (attached).
O O
a b c
O O
d e f
• How would the lmaks values be affected when the solvent is changed from
ethanol to hexane?
KJ 2022/ TKJ 4115 Spectroscopic methods in organic chemistry, Examination June 2. 2006 6
KJ 2022/ TKJ 4115 Spectroscopic methods in organic chemistry, Examination June 2. 2006 7