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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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

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter14: Mass Spectrometry

Section: Chapter Questions

Problem 14.37P

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Concept explainers

NMR Spectroscopy

NMR stands for Nuclear Magnetic Resonance in which the study of different molecules is done based on the interaction of radiofrequency electromagnetic radiations with the nuclei of molecules placed in a strong magnetic field. A precise study of spectra of visible light and all bands of electromagnetic radiation is called spectroscopy.

Question

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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