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Answers
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4.
a.
Increasing the concentration of the nucleophile favors an
S
N
1
reaction over an
S
N
2
reaction.
F
b.
Ethyl iodide is more reactive than ethyl chloride in an
S
N
2
reaction.
T
c.
In an
S
N
1
reaction, the product with the retained configuration is obtained in greater yield.
F
d.
The rate of a substitution reaction in which none of the reactants is charged will increase
if the polarity of the solvent is increased.
T
e.
An
S
N
2
reaction is a two-step reaction.
F
f.
The
p
K
a
of a carboxylic acid is greater in water than it is in a less polar solvent.
F
g.
4-Bromo-1-butanol forms a cyclic ether faster than does 3-bromo-1-propanol.
T
5.
a.
CH
3
O
-
b.
CH
3
S
-
6.
a.
CH
3
CH
2
CH
2
Cl
+
HO
-
c.
CH
3
CH
2
CH
2
Br
+
HO
-
e.
BrCH
2
CH
2
CH
2
CH
2
NHCH
3
b.
CH
3
CH
2
CH
2
I
+
HO
-
d.
CH
3
CHCH
3
Br
CH
3
O
−
CH
3
OH
7.
All are aprotic solvents except ethanol.
8.
a.
The rate of the reaction would increase.
d.
The
p
K
a
would decrease.
b.
The rate of the reaction would increase.
e.
The
p
K
a
would decrease.
c.
The rate of the reaction would decrease.
9.
a.
CH
2
CHCH
3
Br
b.
CHCH
2
CHCH
3
Br
CH
2
10.
CH
3
CHBr
CH
3
11.
C C
major
H
H
3
C
H
CH
3
C C
minor
CH
3
H
3
C
H
H
CH
3
CH
2
H
OCH
3
CH
3
12.
a.
CH
3
CH
2
CO
−
CH
3
CH
3
+
CH
3
CH
2
CH
2
Br
b.
Br
+
O
−
c.
−
+
CH
3
Br
CH
3
CH
2
CH O
2
13.
a.
CH
3
CHCH
3
+
HO
−
Cl
c.
CH
3
CH
2
CH
2
Br
+
HO
-
e.
CH
3
CCH
3
CH
3
Br
+
HO
−
b.
CH
3
CH
2
CH
2
I
+
HO
-
d.
CH
3
CHCH
3
Br
CH
3
O
−
CH
3
OH