Mass Spectrum (not shown): 189 m/z (100%) IR Spectrum (not shown): 3042, 2982, 2932, 2246 (m), 1601, 1498 cm¹ (all listed are strong (s) unless otherwise indicated) ¹H NMR Spectrum (400MHz, CDCl3, 25 °C) m m 8 2H 3H PPM 2H S 2H 6H 13C NMR Spectrum (with DEPT), proton-decoupled (125 MHz, CDCl3, 25°C) (CH) (CH) (C) (CH)(C) (CH2) (CH2)(C) T T 160 140 120 100 80 60 PPM T S (CH3) 40 20

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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Provide the unknown for the given data

Mass Spectrum (not shown): 189 m/z (100%)
IR Spectrum (not shown): 3042, 2982, 2932, 2246 (m), 1601, 1498 cm¹ (all listed are strong (s) unless
otherwise indicated)
¹H NMR Spectrum (400MHz, CDCl3, 25 °C)
m m
8
2H 3H
PPM 2H
S
2H
6H
13C NMR Spectrum (with DEPT), proton-decoupled (125 MHz, CDCl3, 25°C)
(CH)
(CH)
(C)
(CH)(C)
(CH2)
(CH2)(C)
T
T
160
140
120
100
80
60
PPM
T
S
(CH3)
40
20
Transcribed Image Text:Mass Spectrum (not shown): 189 m/z (100%) IR Spectrum (not shown): 3042, 2982, 2932, 2246 (m), 1601, 1498 cm¹ (all listed are strong (s) unless otherwise indicated) ¹H NMR Spectrum (400MHz, CDCl3, 25 °C) m m 8 2H 3H PPM 2H S 2H 6H 13C NMR Spectrum (with DEPT), proton-decoupled (125 MHz, CDCl3, 25°C) (CH) (CH) (C) (CH)(C) (CH2) (CH2)(C) T T 160 140 120 100 80 60 PPM T S (CH3) 40 20
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