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Hydrocarbon Review and Practice
Read p. 8 ² 18 of the textbook and answer these questions..
1. Butane exists in the form of two structural isomers. Draw the structural formula and
write the IUPAC name of each.
H H H H
H C
C
C
C
H
H
H H
H C C C H
H
H
H C H
H
H H H H
butane
(2-)methylpropane
2. Draw the condensed straight-chain structures for heptane and nonane.
CH3CH2CH2CH2CH2CH2CH3
CH3CH2CH2CH2CH2CH2CH2CH2CH3
3. Match each name in a-d with the correct structure in e-h.
D) 3-ethylhexane
A) 3-ethyl-2-methylhexane
H
a.
H
H
H
H
H
H
C
C
C
C
C
H
H H C H
H
H
H
f.
H
C
C
C
H
H
H
H
H
H
H
C
C
C
C
H
H
H
H
H
H
H C H
H
C
H
H
C
H
H C H
H
H
C) 2,2- dimethylhexane
B) 3-ethyl-4-methylhexane
g.
h.
H
H C H
H
H C
C
H
H C H
H
H
H
H
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
C
C
C
H
H
H
H
C
H
H
C
H
C
H
H
H
C
C
C
H
H
H
H
4. Write the names of the following alkanes:
a.
H
H
H
H
C
C
C
H
H
C
H
H
methylpropane
H
H
1
H
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H
b.
H
H
H
C
C
H
C
H
H
C
H
H
H
C
C
H
H
H
2,2-dimethylbutane
H
H
H
c.
H
H
H
H
C
C
H
H
C
C
H
C
3-ethyl-2-methylpentane
H
H
H
C
C
C
H
H
H
H
H
H
5. How many hydrogen atoms would be in a molecule of an alkane containing 15 carbon
atoms? 50 carbon atoms?
CnH2n+2 = C15H32
C50H102
6. Draw the condensed structural formulas of the following compounds:
a. 2-methylbutane
CH3
CH3 CH CH2 CH3
b. 3,3-dichlorohexane
Cl
CH3 CH2 C
CH2
CH2 CH3
Cl
c. 4-ethyl-2,3,4-trimethyldecane
CH3
CH3 CH2
CH3 CH CH C CH2 CH2 CH2 CH2 CH2 CH3
CH3
CH3
7. Write the correct name for each of the following structures:
H
a.
c
H
Br Br H
H
H
H
C
C
C
C
C
C
H
Br H C H H
H
H
H
H
H
2,2,3-tribromo-3-methylhexane
b.
Cl
H
H
H
C
C
C
C
C
H
H
Cl
H
H
H
2,3-dichloropentane
H
H
H
H H
H
C
C
C
C C
C
d
H
H
H
H
C
H
H
H H
C
H
C
H
4-ethyl-2-methylhexane
H
H
H
H
H
H
H
H
C
C
H
H
H
C
H
H
C
H
C
H
H
H
C
H
H
H
C
C
C
C
H
H
H
H
H
3,3,5-trimethylheptane
2
H
SCH4U
Alkanes, Alkenes, Alkynes and Cyclics
Name or draw the following compounds:
Chemical structure
1
IUPAC Name
2-chlorobutane
Cl
H3 C
CH2
CH CH3
CH3
2
CH2
H3 C
CH
CH2
HC
3,5-dimethylheptane
CH3
CH2
CH3
3
Br
H3C CH
Br
CH2
Cl
CH
CH
C
CH3
Cl
CH3
4,6-dibromo-2,2-dichloro-3-methylheptane
CH3
4
CH2
H3 C C
NO2
CH2
CH2
CH
CH2
CH2
3-amino-5-ethyl-5-methyl-1-nitroheptane
NH 2
CH3
5
CH3
H3C CH CH2 C CH2
CH3
CH3
2,4,4-trimethylhexane
CH3
CH3
6
CH2
Cl
HC CH2
CH
CH2
CH
CH3
2,3,7-trichloro-5-ethyloctane
Cl
Cl CH
CH3
7
NH2
NH2
H3C C CH2
NO2
8
Cl
Cl C CH2
Cl
2,4-diamino-2,3-dinitropentane
C CH3
NO2
Cl
Cl
C CH2
C CH3
Cl
Cl
1,1,1,3,3,5,5-heptachlorohexane
CH3
9
CH2
H3 C
C
Br
CH2
CH
CH3
2-bromo-4,4-dimethylhexane
CH3
10
Br
H3C CH2
C CH2
CH3
3-bromo-3-chloropentane
Cl
11
NO2
H3C CH
Br
CH2
1-bromo-3-nitrobutane
CH2
3
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Cl
12
CH3
2,3-dichloropentane
CH CH CH2 CH3
Cl
CH3
13
3-bromo-2-methylheptane
CH3 CH CH CH2 CH2 CH2 CH3
Br
CH3
Cl
14
1,2-dichloropropene
C C
H
Cl
(trans geometric isomer)
4,4-diamino-2,3,6-trichlorooctane
15
Cl Cl
16
CH3 C
C
2,2,3,3,4-pentachloropentane
CH CH3
Cl Cl Cl
17
H3C CH2
CH
CH2
CH3
CH2
18
H3C CH2
19
CH
2-ethyl-1-pentene
C CH2
CH2
CH3
Cl
H3C CH
CH
3-hexene
CH
4-chloro-5-nitro-2-hexene
CH
CH3
CH
CH3
2,3,4-trichlorohexane
CH3
2,3-dibromo-5,5-dimethyl-2-hexene
NO2
Cl
20
H3C CH2
CH
CH
Cl
21
CH3
H3C C
CH2
Cl
Br
Br
C
C
CH3
CH3
22
Cl
HC CH2
CH
C CH3
5-chloro-3-methyl-2-hexene
CH3
4
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23
H3C
CH3
CH3
C
C
CH3
CH3
CH2
Cl
Cl
C
C
CH2
Cl
24
CH3
3,4-dichloro-6,6,7,7-tetramethyl-3-octene
5-amino-3-chloro-1-pentene
CH2 CH CH CH2 CH2
NO2
NO2
26
Cl
CH3 C CH C CH2 CH2 CH3
4-chloro-2,2-dinitro-3-heptene
NO2
27
28
CH3 CH2
H
C C
H
CH2 CH CH2 CH3
Cl
H3C
C
C
C
trans-3-octene
4,4-dichloro-2-pentyne
CH3
Cl
29
HC
30
C
H3C
3,4-dibromo-1-hexyne
Br
Br
CH
CH
C
CH2
C
CH3
CH3
CH3
31
CH3 C C CH2 C CH3
2-butyne
5,5-dimethyl-2-hexyne
CH3
32
CH3
CH2 C C
CH CH2 CH3
NH2
CH3CH2CH2CH2CH3
33
5-amino-3-heptyne
CH3CH CHCH2CH3
a. pentane
b. 2-pentene
c. 1-pentyne
CH CCH2CH2CH3
34
H2C
H3C CH
CH
CH3
35
CH3
1,3-dimethylcyclobutane
CH2
1-methylcyclopropene
C2 H5
36
1,2-diethylcyclopentane
C2 H5
5
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H
H
H
C
37
H
C
H
C
H
C
C
H
H
H
2-methyl-2-butene
H
H
38
39
40
H
C
H
H
H
C
H
H
H
H
C
C
H
H
C
propene
C
H
H
C
C
C
H
2-pentyne
H
C
ethyne
H
41
cyclohexane
H
H
C
H
42
1,2-dimethylcylohexane
H
C
H
H
5-isopropyl-2-methyloctane
44
(C12H26)
45
(recall that in line diagrams, lines represent
carbon-carbon bonds; this contains
isopropyl)
trans-5-ethyl-4,6-dimethyl-2-octene
(C12H24)
46
(C9H16)
47
H2N
1,3-diaminopropane
(line diagram)
NH2
trans-5-ethyl-4,5-dimethyl-2-heptene
(line diagram)
48
49
4-nonyne
H3C
H
C
H
trans-2-hexene
C
CH2 CH2
CH3
6