Complete the spectroscopy data tables for a compound with molecular formula C5H13N.  Determine the structure of the compound. Any labile protons, if they exist, will not be present in this particular 1H NMR spectrum.

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 14.27P: Following is the mass spectrum of an unknown compound. The two highest peaks are at m/z 120 and 122....
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Complete the spectroscopy data tables for a compound with molecular formula C5H13N. 
Determine the structure of the compound. Any labile protons, if they exist, will not be
present in this particular 1H NMR spectrum.

8) Complete the spectroscopy data tables for a compound with molecular formula C5H13N.
Determine the structure of the compound. Any labile protons, if they exist, will not be
present in this particular 1H NMR spectrum.
100
D
4000
3000
2000
ISDO
1000
S00
HAVENUMB ERI 1
1.90
f1 (ppm)
1.95
1.85
3.0 2.9
2.8
2.7
2.6
2.5
2.4
2.3
2.2
2.1 2.0
1.9 1.8 1.7
1.6 1.5 1.4
1.3 1.2 1.1 1.0
0.9
130 120 110 100
f1 (ppm)
90
80 70
60 50
40
30
20
10 0
TRANSHITTANCEI%I
Fooz
1.01.
5.98-
Transcribed Image Text:8) Complete the spectroscopy data tables for a compound with molecular formula C5H13N. Determine the structure of the compound. Any labile protons, if they exist, will not be present in this particular 1H NMR spectrum. 100 D 4000 3000 2000 ISDO 1000 S00 HAVENUMB ERI 1 1.90 f1 (ppm) 1.95 1.85 3.0 2.9 2.8 2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 1.0 0.9 130 120 110 100 f1 (ppm) 90 80 70 60 50 40 30 20 10 0 TRANSHITTANCEI%I Fooz 1.01. 5.98-
8 Degrees of Unsaturation (show work):
DOU = 0
%3D
[2 (5) +2-13+1-0]
2.
1°C NMR Data Table
IR Data Table
Stretch (cm)
Bond
BC Signal Chemical Shift (ppm) PC Signal
> 3000 cm
H-N
44
C-H sp3
2
42ppam
~3000 cm'
26 ppm
4
23
'H NMR Data Table
'H Signal Chemical Shift (ppm) Integration
Multiplicity
to
A
2.75ppm
2H
Proposed Structure
1.90ppm
1.54ppm
2H
CH3
0.95ppm
6 H
H, N-C-C-CH3
CH3
Transcribed Image Text:8 Degrees of Unsaturation (show work): DOU = 0 %3D [2 (5) +2-13+1-0] 2. 1°C NMR Data Table IR Data Table Stretch (cm) Bond BC Signal Chemical Shift (ppm) PC Signal > 3000 cm H-N 44 C-H sp3 2 42ppam ~3000 cm' 26 ppm 4 23 'H NMR Data Table 'H Signal Chemical Shift (ppm) Integration Multiplicity to A 2.75ppm 2H Proposed Structure 1.90ppm 1.54ppm 2H CH3 0.95ppm 6 H H, N-C-C-CH3 CH3
Expert Solution
Step 1

 

Degree of unsaturation is 0 

IR 

3000 cm-1 due to Some C-H bond .

3300 cm-1  due to N-H bond .

NMR 

0.9 6 H doublet 

 

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