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428 Chapter 12
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7.
a.
Draw the products that are obtained from the monochlorination of the following alkane at room
temperature. (Ignore stereoisomers.)
+
Cl
2
CH
3
CCH
2
CH
2
CHCH
3
CH
3
CH
3
CH
3
hv
b.
Which product is obtained in greatest yield?
c.
Which product would be obtained in greatest yield if the alkane is brominated instead of chlorinated?
8.
Calculate the yield of 2-chloro-2-methylbutane (as a percentage of all the monochlorinated products
obtained) when 2-methylbutane is chlorinated in the presence of light at room temperature.
9.
What is the major product of each of the following reactions? Ignore stereoisomers.
a.
CH
3
CH CCH
2
CH
3
CH
3
+
HBr
c.
CH
3
CH CCH
2
CH
3
CH
3
+
HCl
b.
CH
3
CH CCH
2
CH
3
CH
3
+
HBr
peroxide
d.
CH
3
CH CCH
2
CH
3
CH
3
+
HCl
peroxide
10.
Which of the above reactions forms more than one stereoisomer?