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184 Chapter 4
Copyright © 2017 Pearson Education, Inc.
Chapter 4 Practice Test
1.
Are the following pairs of compounds identical or a pair of enantiomers?
a.
H
CH
3
CH
2
OH
CH
3
CH
2
CH
3
CH
2
OH
CH
2
CH
3
H
and
b.
CH
2
CH
3
C
H
Cl
CH
3
C
CH
2
CH
3
Cl
H
and
CH
3
2.
Label the following substituents in order from highest priority to lowest priority in the
E
,
Z
system of
nomenclature.
CCH
3
O
CH CH
2
Cl
C N
3.
100 mL of a solution containing 0.80 g of a compound rotates the plane of polarization of plane-polarized
light
-
4.8
°
in a polarimeter with a 2 dm sample tube. What is the specific rotation of the compound?
4.
Which are meso compounds?
CH
3
H Cl
Cl
H
CH
2
CH
3
CH
3
H Cl
H
Cl
CH
2
CH
3
CH
3
Br
Cl
Cl
Br
CH
2
Cl
CH
3
H Cl
Cl
H
CH
3
CH
3
Cl
H
Cl
H
CH
3
5.
Draw all the constitutional isomers with molecular formula
C
4
H
9
Cl.
6.
Do the following compounds have the
E
or the
Z
configuration?
a.
CH
3
CH
CH
3
CHCH
2
C C
CH
2
OH
CH
2
CH
2
CH
2
Br
CH
3
CH
3
b.
C C
CH
2
OH
C
O
CH
3
CH
Cl
CH
3
CH
CH
3
CH
3
7.
Draw all the possible stereoisomers for each compound that has them.
a.
OH
HO
d.
CH
3
CH
2
CHCH
2
CH
2
Cl
Cl
b.
CH
3
CHCHCH
2
CH
3
Br Br
e.
OH Br
c.
CH
3
CH
2
CHCH
2
CH
3
Cl
f.
HO
CH
3