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Chapter 14 473
Copyright © 2017 Pearson Education, Inc.
57.
CH
3
CCH
3
Cl
CH
3
CH
3
CHCH
2
CH
3
Cl
tert
-butyl chloride
Compound
A
sec
-butyl chloride
Compound
B
58.
CH
3
CH
2
CH CH
2
C C
H
3
C
CH
3
H
H
CH
3
C CH
2
CH
3
cis
-2-butene
1-butene
2-methylpropene
It would be better to use
13
C
NMR because you would have to look only at the number of signals in
each spectrum: 1-butene will show four signals,
cis
-2-butene will show two signals, and 2-methylpropene
will show three signals. (In the
1
H
NMR spectrum, 1-butene will show five signals, and
cis
-2-butene and
2-methylpropene will both show two signals.)
59.
D
B
A
C
OCH
2
CH
3
2
CH
3
OCHCH
3
CH
3
2
O
O
C
CH
3
CH OCH
3
3
O
C
CH
OCH
2
CH
O
C
H
C
H
three signals
singlet, quartet, triplet
(singlet farthest downfield)
three signals
singlet, quartet, triplet
(quartet farthest downfield)
four signals
singlet, triplet
multiplet, triplet
three signals
singlet, septet
doublet
C
can be distinguished from
A, B,
and
D
because
C
has four signals and the others have three signals.
D
can be distinguished from
A
and
B
because the three signals of
D
are a singlet, a septet, and a doublet,
whereas the three signals of
A
and
B
are a singlet, a quartet, and a triplet.
A
and
B
can be distinguished because the highest frequency signal in
A
is a singlet, whereas the highest
frequency signal in
B
is a quartet.
60.
It is the
1
H NMR spectrum of 2,3-dimethylbutane.
CH
3
CHCHCH
3
CH
3
CH
61.
It is the
1
H
NMR spectrum of
tert
-butyl methyl ether.
+
CH
3
C O
−
CH
3
CH
3
CH
3
C OCH
3
CH
3
CH
3
CH
3
Br
tert
-butyl methyl ether