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Chapter 3 151
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d.
Three of the carbon–carbon bonds have staggered conformers that are equally stable, because each is
bonded to a carbon with three identical substituents.
CH
3
CH
CH
3
CH
2
CH
2
CH
2
CH
3
72.
3 2 2 2 2
CH CH CH CH CH Br
a.
1-bromopentane
b.
pentyl bromide
primary alkyl halide
CH
3
CH
2
CH
2
CHCH
3
Br
a.
2-bromopentane
b.
no common name
secondary alkyl halide
CH
3
CH
2
CHCH
2
CH
3
Br
a.
3-bromopentane
b.
no common name
secondary alkyl halide
CH
3
CHCH
2
CH
2
Br
CH
3
a.
1-bromo-3-methylbutane
b.
isopentyl bromide
primary alkyl halide
CH
3
CH
2
CHCH
2
Br
CH
3
a.
1-bromo-2-methylbutane
b.
no common name
primary alkyl halide
CH
3
CH
2
CCH
3
CH
3
Br
a.
2-bromo-2-methylbutane
b.
tert
-pentyl bromide
tertiary alkyl halide
CH
3
CHCHCH
3
CH
3
Br
a.
2-bromo-3-methylbutane
b.
no common name
secondary alkyl halide
CH
3
CCH
2
Br
CH
3
CH
3
a.
1-bromo-2,2-dimethylpropane
b.
no common name, but in older
literature, the common name
neopentyl bromide can be found.
primary alkyl halide
c.
Four isomers are primary alkyl halides.
d.
Three isomers are secondary alkyl halides.
e.
One isomer is a tertiary alkyl halide.
73.
a.
butane
b.
1-propanol
c.
5-propyldecane
d.
4-propyl-1-nonanol
e.
2-methyl-5-(1-methylethyl)octane or
5-isopropyl-2-methyloctane
f.
6-chloro-4-ethyl-3-methyloctane
g.
1-methoxy-5-methyl-3-propylhexane
h.
2,3-dimethyl-6-(2-methylpropyl)decane or
6-isobutyl-2,3-dimethyldecane
i.
8-methyl-4-decanamine
j.
1-methyl-2-(2-methylpropyl)cyclohexane
or 1-isobutyl-2-methylcyclohexane
74.
a.
CH
3
CH
2
CH
3
more stable
CH
3
CH
2
CH
3