Mass spectrometry of an unknown compound revealed a molecular ion at m/z 100.09. The IR spectrum, the ¹³C NMR spectrum, and the ¹H NMR spectrum are shown below. Draw the structure of this compound. 4000 3000 2000 TM 1500 Wavenumbers (cm-¹) 140 REM 100 1H A 1000 500

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter12: Structure Determination: Mass Spectrometry And Infrared Spectroscopy
Section12.SE: Something Extra
Problem 15AP: Write molecular formulas for compounds that show the following molecular ions in their...
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Mass spectrometry of an unknown compound revealed a
molecular ion at m/z 100.09. The IR spectrum, the ¹³C NMR
spectrum, and the ¹H NMR spectrum are shown below. Draw
the structure of this compound.
4000
220
3000
200 180
160
2000
M
1500
Wavenumbers (cm-¹)
140 120 100
1H
80
6H
1000
40
3H
20
ppm
500
Transcribed Image Text:Mass spectrometry of an unknown compound revealed a molecular ion at m/z 100.09. The IR spectrum, the ¹³C NMR spectrum, and the ¹H NMR spectrum are shown below. Draw the structure of this compound. 4000 220 3000 200 180 160 2000 M 1500 Wavenumbers (cm-¹) 140 120 100 1H 80 6H 1000 40 3H 20 ppm 500
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