Compound C has the molecular formula of C6H12O2 with the following IR data. The mass and NMR (1H and 13C NMR) spectra are shown below. IR (cm-1): 2800, 2950, 1710 and 1120 cm-1 зН (s)'H NMR6H (d)2H (d)1H (m)32ppm19.413C NMR21.170.428.2171.21901801601401201006020 ppmo8040100 -MS80 -604020 -1020304070801005060m/z90(i) Explain how the IR, 'H and 13C NMR spectra can be used to deduce the structure of C.(ii)Based on the mass spectrum, identify the base peak of compound C.(iii) Draw the possible cation for the base peak in (iv) and its resonance structure (if any).Relative Intensity

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Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

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Compound C has the molecular formula of C6H12O2 with the following IR data. The mass and NMR (1H and 13C NMR) spectra are shown below. IR (cm-1): 2800, 2950, 1710 and 1120 cm-1

зН (s)
'H NMR
6H (d)
2H (d)
1H (m)
3
2
ppm
19.4
13C NMR
21.1
70.4
28.2
171.2
190
180
160
140
120
100
60
20 ppmo
80
40
100 -
MS
80 -
60
40
20 -
10
20
30
40
70
80
100
50
60
m/z
90
(i) Explain how the IR, 'H and 13C NMR spectra can be used to deduce the structure of C.
(ii)
Based on the mass spectrum, identify the base peak of compound C.
(iii) Draw the possible cation for the base peak in (iv) and its resonance structure (if any).
Relative Intensity

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