Mass Spectrum (not shown): [M] = 208 (100%) m/z IR Spectrum (not shown): 3098, 2981, 1331 cm³¹ (all listed are strong (s) unless otherwise indicated) ¹H NMR Spectrum (400 MHz, CDCI3, 25 °C) 8 t (J= 8 Hz) Q1.R 1H 7 160 dd (J= 8, 2 Hz) t (J= 2 Hz) 2H 1H 6 140 1³C NMR Spectrum, proton-decoupled (125 MHz, CDCI3, 25 °C) (C) (CH) 5 120 (CH) (CH) m 100 4 PPM 4H PPM 3 (CH₂) (CH₂) 80 60 2 m 4H 2H (CH₂) 40 m 6H (CH₂)(CH₂) (CH3) \/ 20 0 (CH3) O 1/1

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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Given the Mass Spectrum, IR spectrum, and C/H NMR spectrum, what is the spectroscopy unknown or a molecule that matches this data.
Mass Spectrum (not shown): [M] = 208 (100%) m/z
IR Spectrum (not shown): 3098, 2981, 1331 cm³¹ (all listed are strong (s) unless otherwise indicated)
¹H NMR Spectrum (400 MHz, CDCI3, 25 °C)
8
t (J= 8 Hz)
Q1.R
1H
7
160
dd (J= 8, 2 Hz)
t (J= 2 Hz)
2H 1H
6
140
1³C NMR Spectrum, proton-decoupled (125 MHz, CDCI3, 25 °C)
(C)
(CH)
5
120
(CH)
(CH)
m
100
4
PPM
4H
PPM
3
(CH₂) (CH₂)
80
60
2
m
4H 2H
(CH₂)
40
m
6H
(CH₂) (CH₂) (CH3)
\/
20
0
(CH3)
O
1/1
Transcribed Image Text:Mass Spectrum (not shown): [M] = 208 (100%) m/z IR Spectrum (not shown): 3098, 2981, 1331 cm³¹ (all listed are strong (s) unless otherwise indicated) ¹H NMR Spectrum (400 MHz, CDCI3, 25 °C) 8 t (J= 8 Hz) Q1.R 1H 7 160 dd (J= 8, 2 Hz) t (J= 2 Hz) 2H 1H 6 140 1³C NMR Spectrum, proton-decoupled (125 MHz, CDCI3, 25 °C) (C) (CH) 5 120 (CH) (CH) m 100 4 PPM 4H PPM 3 (CH₂) (CH₂) 80 60 2 m 4H 2H (CH₂) 40 m 6H (CH₂) (CH₂) (CH3) \/ 20 0 (CH3) O 1/1
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