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Chapter 3 135
Copyright © 2017 Pearson Education, Inc.
Solutions to Problems
1.
a.
C
n
H
2
n
+
2
If there are 17 carbons, then there are 36 hydrogens.
b.
C
n
H
2
n
+
2
If there are 74 hydrogens, then there are 36 carbons.
2.
3 2 2 2 2 2 2 3
CH CH CH CH CH CH CH CH
octane
isooctane
CH
3
CHCH
2
CH
2
CH
2
CH
2
CH
3
CH
3
3.
a.
propyl alcohol
b.
butyl methyl ether
c.
propylamine
4.
a.
CH
3
CHCH
2
CH
3
CH
3
b.
CH
3
CCH
3
CH
3
CH
3
2-methylbutane
2,2-dimethylpropane
5.
Notice that each carbon forms four bonds and each hydrogen and bromine forms one bond.
3 2 2 2
CH CH CH CH Br
CH
3
CHCH
2
CH
3
Br
CH
3
CHCH
2
Br
CH
3
CH
3
CCH
3
Br
CH
3
n
-butyl bromide
sec
-butyl bromide isobutyl bromide
tert
-butyl bromide
or
butyl bromide
6.
“Dibromomethane does not have constitutional isomers” proves that carbon is tetrahedral.
If carbon were flat, rather than tetrahedral, dibromomethane would have constitutional isomers because
the two structures shown below would be different since the bromines would be 90° apart in one
compound and 180° apart in the other compound. Only because carbon is tetrahedral are the two structures
identical.
C
H
Br
Br
H
C
Br
H
Br
H
7.
a.
CH
3
CHOH
CH
3
c.
CH
3
CH
2
CHI
CH
3
e.
CH
3
CNH
2
CH
3
CH
3
b.
CH
3
CHCH
2
CH
2
F
CH
3
d.
CH
3
COH
CH
2
CH
3
CH
3
f.
3 2 2 2 2 2 2 2
CH CH CH CH CH CH CH CH Br