2. The following spectra for A and B correspond to two structural isomers with a molecular formula of C.H,N. The NMR singlet at 81.16 in spectrum A disappears when the sample is shaken with Dr0. The singlet at 80.60 ppm in the spectrum of B disappears on shaking with D20. Propose structures for these isomers, and explain how it is consistent with the observed absorptions. wavelength (pum) 25 100 3.5 4,5 9 10 U 12 13 14 15 16 5.5 6. 80 60 40 20 4000 3500 3000 2500 2000 I800 1400 1000 S00 waverumber icm 200 180 160 140 120 60 40

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy
Section13.SE: Something Extra
Problem 59GP: The mass spectrum and 13C NMR spectrum of a hydrocarbon are shown. Propose a structure for this...
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1.1.1
2.1 3
1.4.1
5 1·6·1 7.1 8 9.1. 10.1 11. 12. 1 1B
The following spectra for A and B correspond to two structural isomers with a molecular
formula of C.HnN. The NMR singlet at 81.16 in spectrum A disappears when the sample is
shaken with Dr0. The singlet at 80.60 ppm in the spectrum of B disappears on shaking with
D20. Propose structures for these isomers, and explain how it is consistent with the observed
absorptions.
2.
1.
wavelengih (am)
3.5 6
100
25
3.5
4
4.5
$ 9 10
12 13 14 1S 16
m
80
60
40
AW
20
4000
3500
3000
2500
IKI
SIKI
wanenumber icm
200
180
160
140
120
60
40
在
%3D
Transcribed Image Text:1.1.1 2.1 3 1.4.1 5 1·6·1 7.1 8 9.1. 10.1 11. 12. 1 1B The following spectra for A and B correspond to two structural isomers with a molecular formula of C.HnN. The NMR singlet at 81.16 in spectrum A disappears when the sample is shaken with Dr0. The singlet at 80.60 ppm in the spectrum of B disappears on shaking with D20. Propose structures for these isomers, and explain how it is consistent with the observed absorptions. 2. 1. wavelengih (am) 3.5 6 100 25 3.5 4 4.5 $ 9 10 12 13 14 1S 16 m 80 60 40 AW 20 4000 3500 3000 2500 IKI SIKI wanenumber icm 200 180 160 140 120 60 40 在 %3D
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15. 1
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%3D
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wavelength (um)
5.5 6
8 9 10
25
35
4.5
11
12 13 14 15 16
100
80
60
40
20
4000
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3000
2500
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1600
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10
ppm
Transcribed Image Text:HEADINC Effects imding Heading 1 Colors Fonts kaed Set as Default Document Formatting * . 1 I 2. 1 . 4.1 5. 1 9.1 10 1: 1 12. 13 14. I 15. 1 16 18 %3D %3D wavelength (um) 5.5 6 8 9 10 25 35 4.5 11 12 13 14 15 16 100 80 60 40 20 4000 3500 3000 2500 2000 1800 1600 1400 1200 1000 800 60 wavenumber (em 10 ppm
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