Mass Spectrum (not shown): 182 m/z (100%), 184 m/z (32.2%) IR Spectrum (not shown): 3029, 2961, 2825 (m), 2726 (m), 1726, 1604, 1497 cm-1 (all listed are strong (s) unless otherwise indicated) ¹H NMR Spectrum (400MHz, CDCl3, 25 °C) 10 1H d d 8 2H 2H S PPM 2H t q -2 2 2H 2H 13C NMR Spectrum (with DEPT), proton-decoupled (125 MHz, CDCl 3, 25°C) (CH) (C) (C) 2 x (CH) (CH2 CH2) (CH2) 220 200 180 160 140 120 PPM 100 80 60 - 40 46 20 0

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter14: Mass Spectrometry
Section: Chapter Questions
Problem 14.29P
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Provide the unknown for the given data. 

Mass Spectrum (not shown): 182 m/z (100%), 184 m/z (32.2%)
IR Spectrum (not shown): 3029, 2961, 2825 (m), 2726 (m), 1726, 1604, 1497 cm-1 (all listed are strong (s)
unless otherwise indicated)
¹H NMR Spectrum (400MHz, CDCl3, 25 °C)
10
1H
d
d
8
2H 2H
S
PPM 2H
t q
-2
2
2H 2H
13C NMR Spectrum (with DEPT), proton-decoupled (125 MHz, CDCl 3, 25°C)
(CH)
(C) (C)
2 x (CH)
(CH2 CH2) (CH2)
220
200
180
160
140
120
PPM
100
80
60
-
40
46
20
0
Transcribed Image Text:Mass Spectrum (not shown): 182 m/z (100%), 184 m/z (32.2%) IR Spectrum (not shown): 3029, 2961, 2825 (m), 2726 (m), 1726, 1604, 1497 cm-1 (all listed are strong (s) unless otherwise indicated) ¹H NMR Spectrum (400MHz, CDCl3, 25 °C) 10 1H d d 8 2H 2H S PPM 2H t q -2 2 2H 2H 13C NMR Spectrum (with DEPT), proton-decoupled (125 MHz, CDCl 3, 25°C) (CH) (C) (C) 2 x (CH) (CH2 CH2) (CH2) 220 200 180 160 140 120 PPM 100 80 60 - 40 46 20 0
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