From the IR, MS, UV, 13C NMR and 1H NMR data shown below, identify the unknown organic molecule. Indicate any partial structures that you are able to deduce from these spectra and explain how you identify these. 400010080203284% of base peak300043401013C NMR Spectrum(50.0 MHz, CDCI, solution)IR Spectrum(KBr disc)106MMM.13780120 160m/eDEPT CH₂ CH₂ CHproton decoupled9200¹H NMR Spectrum(200 MHz, CDCI, solution)exchangeswith D₂O on warming200081658V (cm¹)16016007M**1792006120expansion12007.6800Mass SpectrumC10H13 NO2240 2805solvent807.04ppm3UV Spectrummax 250 nm (log, 3.1)Amax 287 nm (log₁0€ 2.2)solvent: chloroform402018 (ppm)TMS08 (ppm)

4000 100 80 20 3284 % of base peak IR Spectrum (KBr disc) 3000 Japan 13C NMR Spectrum 2000 1658 1600 43 106 WAIT 137 40 80 120 160 m/e V (cm¹) M** 179 200 1200 800 Mass Spectrum C10H13 NO2 240 280 UV Spectrum max 250 nm (log, 3.1) Amax 287 nm (log₁0€ 2.2) solvent: chloroform

4000 100 80 20 3284 % of base peak IR Spectrum (KBr disc) 3000 Japan 13C NMR Spectrum 2000 1658 1600 43 106 WAIT 137 40 80 120 160 m/e V (cm¹) M** 179 200 1200 800 Mass Spectrum C10H13 NO2 240 280 UV Spectrum max 250 nm (log, 3.1) Amax 287 nm (log₁0€ 2.2) solvent: chloroform

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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Question

100%

From the IR, MS, UV, ¹³C NMR and ¹H NMR data shown below, identify the unknown organic molecule. Indicate any partial structures that you are able to deduce from these spectra and explain how you identify these.

4000
100
80
20
3284
% of base peak
3000
43
40
10
13C NMR Spectrum
(50.0 MHz, CDCI, solution)
IR Spectrum
(KBr disc)
106
MMM.
137
80
120 160
m/e
DEPT CH₂ CH₂ CH
proton decoupled
9
200
¹H NMR Spectrum
(200 MHz, CDCI, solution)
exchanges
with D₂O on warming
2000
8
1658
V (cm¹)
160
1600
7
M**
179
200
6
120
expansion
1200
7.6
800
Mass Spectrum
C10H13 NO2
240 280
5
solvent
80
7.0
4
ppm
3
UV Spectrum
max 250 nm (log, 3.1)
Amax 287 nm (log₁0€ 2.2)
solvent: chloroform
40
2
0
1
8 (ppm)
TMS
0
8 (ppm)

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