You have mixed up the bottles of the two structural isomers drawn below and decide to use mass spectrometry to distinguish them. Determine which isomer is likely represented by the spectrum below. In addition, draw at least one arrow-pushing fragmentation mechanism that led you to that conclusion. 100- 80- 60- 40- 20- 0- 20 25 31.0 36.1% 29.0 11.1% 1.1 30 HO 2-methylpropan-1-ol 35 41.0 28.7% 39.0 9.4% 40 45 OH to 2-methylpropan-2-ol 50 m/z (Da) 59.0 100.0% 57.0 13.2% 55 I 60 65 70 75 8

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Chapter1: Chemical Foundations
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You have mixed up the bottles of the two structural isomers drawn below and decide to use mass
spectrometry to distinguish them. Determine which isomer is likely represented by the spectrum
below. In addition, draw at least one arrow-pushing fragmentation mechanism that led you to that
conclusion.
100-
80-
60-
40-
20-
0-
20
25
31.0
36.1%
29.0
11.1%
30
HO
2-methylpropan-1-ol
35
41.0
28.7%
39.0
9.4%
40
L.
45
OH
to
2-methylpropan-2-ol
50
m/z (Da)
59.0
100.0%
I
57.0
13.2%
55
I
60
65
70
T
75
8
Transcribed Image Text:You have mixed up the bottles of the two structural isomers drawn below and decide to use mass spectrometry to distinguish them. Determine which isomer is likely represented by the spectrum below. In addition, draw at least one arrow-pushing fragmentation mechanism that led you to that conclusion. 100- 80- 60- 40- 20- 0- 20 25 31.0 36.1% 29.0 11.1% 30 HO 2-methylpropan-1-ol 35 41.0 28.7% 39.0 9.4% 40 L. 45 OH to 2-methylpropan-2-ol 50 m/z (Da) 59.0 100.0% I 57.0 13.2% 55 I 60 65 70 T 75 8
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