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Chapter 4 185
Copyright © 2017 Pearson Education, Inc.
8.
Which of the following three perspective formulas are the same as the Fischer projection shown here?
C
HOOC
H C
H
CH
3
OH
HO
C
HOOC
HO C
OH
CH
3
H
H
C
HOOC
H C
OH
CH
3
H
HO
COOH
HO
H
OH
H
CH
3
9.
1
R
2
-
1
-
2
-2-methyl-1-butanol can be oxidized to
1
+
2
-2-methylbutanoic acid without breaking any of the
bonds to the asymmetric center. What is the configuration of
1
-
2
-2-methylbutanoic acid?
COOH
C
CH
3
oxidation
CH
2
OH
C
H
CH
2
CH
3
CH
3
H
CH
2
CH
3
(
R
)-(
−
)-2-methyl-1-butanol
(
+
)-2-methylbutanoic acid
10.
1
-
2
-Cholesterol has a specific rotation of
-
32.
What would be the observed specific rotation of a solution
that contains
25
,
1
+
2
-cholesterol and
75
,
1
-
2
-cholesterol?
11.
Draw and label the
E
and
Z
stereoisomers of:
a.
1-bromo-2,3-dimethyl-2-pentene
b.
2,3,4-trimethyl-3-hexene
12.
Which of the following have the
R
configuration?
H
Br
CH
3
CH
3
CH
2
CH
3
OH
H
CH
3
CH
2
CH
2
CH
2
Br
Br
CH
3
CH
3
CH
2
OH
H
CH
3
CH
3
CH
2
CH
3
C
CH
2
CH
3
H
HO
CH
3
C
CH
2
CH
3
CH
3
O
H
CH
2
CH
2
CH
3
C
CH
Cl
H
CH
2
CH
2
Br
C
H
Br
CH
3
13.
Answer the following:
a.
Are the following compounds identical or a pair of enantiomers?
H
CH
2
OH
CH
3
CH
3
CH
2
CH
2
OH
CH
3
H CH
2
CH
3