172 / 912
164 Chapter 4
Copyright © 2017 Pearson Education, Inc.
18.
Draw the first enantiomer with the groups in any order you want. Then draw the second enantiomer by
drawing the mirror image of the first enantiomer. Your answer might not look like the ones shown below
because the first enantiomer can be drawn with the four groups on any of the four bonds. The next one is
the mirror image of the first one.
a. 1.
C
CH
3
CH
2
OH
Br
H
C
CH
3
Br
HOCH
2
H
3.
C
OH
CH
3
H
C
OH
CH(CH
3
)
2
H
(CH
3
CH
3
)
2
CH
2.
C
CH
2
CH
2
Cl
CH
2
CH
3
H
C
CH
2
CH
2
Cl
CH
3
H
CH
3
CH
3
CH
2
b. 1.
CH
3
H
CH
2
OH
Br
CH
3
Br
CH
2
OH
H
3.
CH
3
H
CH(CH
3
)
2
HO
CH
3
OH
CH(CH
3
)
2
H
2.
CH
2
CH
2
Cl
CH
3
CH
2
CH
3
H
CH
2
CH
2
Cl
H
CH
2
CH
3
CH
3
19.
Solved in the text.
20.
a.
CH
2
OH
CH
3
CH
2
CH
2
OH
H
1
3
2
4
b.
OH
CH
3
CH
2
OH
CH
2
Br
2
1
4
3
c.
CH(CH
3
)
2
CH
2
CH
2
Br
Cl
CH
2
CH
2
CH
2
Br
2
3
1
4
d.
CH
2
CH
2
forms 2 bonds to
C, so considered
to be attached
to 2 Cs
CH
2
CH
3
3
attached to
1 C
CH
3
4
attached only
to Hs
1
forms 3 bonds to
C, so considered
to be attached
to 3 Cs
21.
Solved in the text.