An unknown compound has the formula C8H9BrO. Determine the structure of this compound through the data from the figures provided. absorbance10.89'00.40.20.80.6arbitrary0.2350030002500602000cm 1Figure 1. IR spectrum (absorbance mode) of the unknown compound80 1001201500140m/zFigure 4. Full MS spectrum of the unknown compound1601000180500 0.8900.4zo1407.60 7.56 7.50 7.45 7.401098120T7.35 7.30 7.252.00100ppmFigure 2. Full ¹3C NMR of the unknown compound in CDCI32.9130 20 1007.20 7.166Hzumu8057.10 7.05 7.00IMPRIPE3.90 3.85460313ANAME__IMINTAMANI3.05 3.00 2.96113ppmFigure 7. ¹H NMR spectrum (in CDCI) of the unknown compound4021.65 1.60200

140 M www 7.60 7.56 7.50 10 9 120 8 T 745 7.40 7.35 7.30 7.25 0.81 100 ppm Figure 2. Full ¹3C NMR of the unknown compound in CDCI, 7 s Hz 30 20 10 0 6 80 5 M 74 7.20 7.16 7.10 7.06 7.00 3.90 ppm 3.85 4 60 $13 Mi r 1.65 1.60 € 11 3 40 3.06 3.00 2.96 2 20 0

140 M www 7.60 7.56 7.50 10 9 120 8 T 745 7.40 7.35 7.30 7.25 0.81 100 ppm Figure 2. Full ¹3C NMR of the unknown compound in CDCI, 7 s Hz 30 20 10 0 6 80 5 M 74 7.20 7.16 7.10 7.06 7.00 3.90 ppm 3.85 4 60 $13 Mi r 1.65 1.60 € 11 3 40 3.06 3.00 2.96 2 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

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.25P

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Question

An unknown compound has the formula C8H9BrO. Determine the structure of this compound through the data from the figures provided.

absorbance
1
0.8
9'0
0.4
0.2
0.8
0.6
arbitrary
0.2
3500
3000
2500
60
2000
cm 1
Figure 1. IR spectrum (absorbance mode) of the unknown compound
80 100
120
1500
140
m/z
Figure 4. Full MS spectrum of the unknown compound
160
1000
180
500

0.8
90
0.4
zo
140
7.60 7.56 7.50 7.45 7.40
10
9
8
120
T
7.35 7.30 7.25
2.00
100
ppm
Figure 2. Full ¹3C NMR of the unknown compound in CDCI3
2.91
30 20 100
7.20 7.16
6
Hz
umu
80
5
7.10 7.05 7.00
IMPRIPE
3.90 3.85
4
60
313
ANAME__IMINTAMANI
3.05 3.00 2.96
11
3
ppm
Figure 7. ¹H NMR spectrum (in CDCI) of the unknown compound
40
2
1.65 1.60
20
0

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