C5H12O MW = 88.

15
C5H12O MW = 88.15
OH
 C5H12O MW = 88.15
OH

+ +
OH OH
H CH3
H3C CH3 H3C H
m/z = 88 m/z = 73
 C5H12O MW = 88.15
OH

+ +
OH OH
H CH3
H3C CH3 H3C H
m/z = 88 m/z = 73
+ +
OH OH
H H3C CH2
H3C CH3
H CH3
m/z = 88 m/z = 45
 C5H12O MW = 88.15
OH

+ +
OH OH
H CH3
H3C CH3 H3C H
m/z = 88 m/z = 73
+ +
OH OH
H H3C CH2
H3C CH3
H CH3
m/z = 88 m/z = 45

+ +
OH +

H3C CH3
m/z = 70 m/z = 70
Solve the structure with no further information
Solve the structure with no further information

Two equally sized peaks

That differ by 2 units:
Bromine
Solve the structure with no further information

Two equally sized peaks

That differ by 2 units:
Bromine

M81
M79
Solve the structure with no further information

+ Two equally sized peaks

CH2 That differ by 2 units:
Bromine

M81
M79
Solve the structure with no further information

+ Two equally sized peaks

CH2 That differ by 2 units:
Bromine

M81
M79

+ +
CH2
Br Br
C9H10O IHD=5
+
CH2
C9H10O IHD=5
+
CH2
C9H10O IHD=5
MCH3
 +
CH2
C9H10O IHD=5
MCH3

The above fragments account for C8H10

 +
CH2
C9H10O IHD=5
MCH3

The above fragments account for C8H10

CH3
CH3
+O
+
O O
+
m/z = 119
 +
CH2
C9H10O IHD=5
MCH3

The above fragments account for C8H10

CH3
CH3 +
+O H2C
+
O m/z = 91
+ O
m/z = 119
 +
CH2
C9H10O IHD=5
MCH3

The above fragments account for C8H10

CH3
CH3 +
+O H2C
+
O m/z = 91
+ O
m/z = 119

CH3
CH3 CH3
O+ +
O O
+
m/z = 43
O O

OEt
 O O

OEt

+O O+
O
O
OEt
OEt

m/z = 105
 O O

OEt

+O O+
O
O
OEt
OEt

m/z = 105

+
O O O O+
OEt
OEt
m/z = 73
 O O

OEt

+O O+
O
O +
OEt
OEt CO

m/z = 105 m/z = 77

+
O O O O+
OEt
OEt
m/z = 73
 43
57 A
72

29 113
85

142

O
43 B 1
71

58 99
2 O
86
match the
142 compound to
it's spectrum
 43 A 43 B
57
72
71

29 113
58 99
85
86
142
142
 43 A 43 B
57
72
71

29 113
58 99
85
86
142
142

O+
+ +
O

m/z = 85
m/z = 113
 43 A 43 B
57
72
71

29 113
58 99
85
86
142
142

O+
+ +
O

m/z = 85
m/z = 113

O+ O+
+

m/z = 29
m/z = 57
 43 A 43 B
57
72
71

29 113
58 99
85
86
142
142

O+
+ +
O

m/z = 85
m/z = 113

O+ O+
+

m/z = 29
m/z = 57
McLafferty H +
O+
OH
rearrangement
m/z = 72
 43 A 43 B
57
72
71

29 113
58 99
85
86
142
142

O+
+ +
O

m/z = 85
m/z = 113

O+ O+
+

m/z = 29
m/z = 57
H +O O+
McLafferty O+
+
OH
rearrangement
m/z = 72 m/z = 43
 43 O
A 43 B
57
72 1
71

29 113
58 99
85
86
142
142

O+
+ +
O

m/z = 85
m/z = 113

O+ O+
+

m/z = 29
m/z = 57
H +O O+
McLafferty O+
+
OH
rearrangement
m/z = 72 m/z = 43
 43
43
57
72
71

29 113
58 99
85
86
142
142

O+
+O +

m/z = 71
m/z = 99
 43
43
57
72
71

29 113
58 99
85
86
142
142

O+ O+

O+
+O + +

m/z = 71 m/z = 43
m/z = 71
m/z = 99
 43
43
57
72
71

29 113
58 99
85
86
142
142

O+ O+

O+
+O + +

m/z = 71 m/z = 43
m/z = 71
m/z = 99

H +OH
McLafferty O+

rearrangement
m/z = 86

+ H +
O OH

m/z = 114
NOT OBSERVED
 43
43
57
72
71

29 113
58 99
85
86
142
142

O+ O+

O+
+O + +

m/z = 71 m/z = 43
m/z = 71
m/z = 99

H +OH
McLafferty O+

rearrangement
m/z = 86

+ H + H + +
Double O OH O OH
McLafferty
m/z = 114 m/z = 58
rearrangement NOT OBSERVED
 43 O O
43
57
72
71

29 113
58 99
85
86
142
142

O+ O+

O+
+O + +

m/z = 71 m/z = 43
m/z = 71
m/z = 99

H +OH
McLafferty O+

rearrangement
m/z = 86

+ H + H + +
Double O OH O OH
McLafferty
m/z = 114 m/z = 58
rearrangement NOT OBSERVED
Trans-2-butenal
3-butyn-2-ol
o-nitrotolueno