Chapter12: Structure Determination: Mass Spectrometry And Infrared Spectroscopy
Section12.SE: Something Extra
Problem 46AP: Ketones undergo a reduction when treated with sodium borohydride, NaBH4. What is the structure of...
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Analyze the spectral data for 4-cyclohexene-cis-1,2-dicarboxylic acid
1. Assign the peaks in the region above 1600 cm-1 of the IR.
2. In the 1H NMR spectrum, assign the various resonances to the hydrogen nuclei responsible for them.
3. What should the integral be for the peak at 12.25 ppm?
4. Write the 1H NMR spectral information in ACS format.
5. For the 13C NMR data, assign the resonances to the carbon nuclei responsible for them.
6. Can you tell whether you have the cis or trans 4-cyclohexene-1,2-dicarboxylic acid based on the number of signals seen on 13C NMR? Why or why not?
Transcribed Image Text:anhydride (CDCI3).
(b) 13C NMR data: 8 47.6, 53.5, 136.1, 171.9.
100
80
60 -
40
CO2H
20 -
"CO2H
Figure 12.11
IR spectrum of 4-cyclohexene-
cis-1,2-dicarboxylic acid (IR card).
T
4000
3600
3200
2800
2400
2000
1800
1600
1400
1200
1000
800
600
Wavenumber (cm-1)
CO2H
|に
"CO2H
CD3SOCD,H
IIT
12.4 ppm
2.94 ppm
2.40
ppm
22
10
9.
8
7
6
4
3
2
1
Figure 12.12
NMR data for 4-cyclohexene-
cis-1,2-dicarboxylic acid
(DMSO-d,).
8, ppm
пе-
(a) 'H NMR spectrum (300 MHz).
(b) 13C NMR data: 8 25.9, 39.2, 125.2, 174.9.
Transmittance (%)
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