Mass Spectrum (not shown): 162 m/z (100%) IR Spectrum (not shown): 3031, 2972, 2934, 1712, 1604, 1495 cm³¹ (all listed are strong (s) unless otherwise indicated) 1H NMR Spectrum (400MHz, CDCl3, 25 °C) m S d m 8 6 5 5H 4 PPM 3 2 2H 1H 6H 13C NMR Spectrum (with DEPT), proton-decoupled (125 MHz, CDCl3, 25°C) 2 x (CH) (C) (C) (CH) (CH2) (CH) (CH3) 220 200 180 160 140 120 100 80 60 40 8- 20 PPM 20 0

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 details. 

Mass Spectrum (not shown): 162 m/z (100%)
IR Spectrum (not shown): 3031, 2972, 2934, 1712, 1604, 1495 cm³¹ (all listed are strong (s) unless otherwise
indicated)
1H NMR Spectrum (400MHz, CDCl3, 25 °C)
m
S
d
m
8
6
5
5H
4
PPM
3
2
2H
1H
6H
13C NMR Spectrum (with DEPT), proton-decoupled (125 MHz, CDCl3, 25°C)
2 x (CH)
(C)
(C) (CH)
(CH2) (CH)
(CH3)
220
200
180
160 140
120
100
80
60
40
8-
20
PPM
20
0
Transcribed Image Text:Mass Spectrum (not shown): 162 m/z (100%) IR Spectrum (not shown): 3031, 2972, 2934, 1712, 1604, 1495 cm³¹ (all listed are strong (s) unless otherwise indicated) 1H NMR Spectrum (400MHz, CDCl3, 25 °C) m S d m 8 6 5 5H 4 PPM 3 2 2H 1H 6H 13C NMR Spectrum (with DEPT), proton-decoupled (125 MHz, CDCl3, 25°C) 2 x (CH) (C) (C) (CH) (CH2) (CH) (CH3) 220 200 180 160 140 120 100 80 60 40 8- 20 PPM 20 0
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