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436 Chapter 13
Copyright © 2017 Pearson Education, Inc.
16.
All three ketones have a molecular ion with
m
>
z
=
86.
O
86 – 29
=
57
O
86 – 43
=
45
O
86 – 43
=
45
The first one will have a base peak at
m
>
z
=
57, whereas the other two ketones will have base peaks
at
m
>
z
=
43.
The second one will have a peak at
m
>
z
=
58 due to a McLafferty rearrangement.
The third one does not have any
g
-hydrogens. Therefore, it cannot undergo a McLafferty rearrangement,
so it will not have a peak at
m
>
z
=
58.
17.
a.
CH
3
CH
2
CH
2
CH
2
CH
2
OH
−
e
−
CH
3
CH
2
CH
2
CH
2
CH
2
OH
-cleavage
CH
3
CH
2
CH
2
CH
2
+
CH
2
OH
m
/
z
=
31
m
/
z
=
88
CH
3
CH
2
CHCH
2
CH
2
OH
H
CH
3
CH
2
CHCH
2
CH
2
+
m
/
z
=
70
+
H
2
O
+
+
+
•
•
•
•
b.
CH
3
CH
2
CHCH
2
CH
2
CH
2
CH
3
−
e
−
-cleavage
CH
3
CH
2
+
m
/
z
=
87
CH
3
CH
2
CH
2
CH
2
CH OH
CH
3
CH
2
CH
2
CH
2
CH
3
CH
2
CHCH
2
CH
2
CH
2
CH
3
m
/
z
=
116
+
-cleavage
+
m
/
z
=
59
CH
3
CH
2
CH OH
+
OH
OH
+
CH
3
CH
2
CH CH
2
CH
2
CH
2
CH
3
OH
+
CH
2
CH
2
CHCH
2
CH
2
CH
2
CH
3
OH
CH
2
CH
2
CHCH
2
CH
2
CH
2
CH
3
H
2
O
+
H
+
+
m
/
z
=
98
CH
3
CH
2
CHCH
2
CHCH
2
CH
3
OH
+
H
CH
3
CH
2
CHCH
2
CHCH
2
CH
3
H
2
O
+
+
m
/
z
=
98
•
•
•
•
•
•
•