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502 Chapter 15
Copyright © 2017 Pearson Education, Inc.
so formation of the new ester by reaction of the alcohol with the charged amide will be faster than forma-
tion of the ester by reaction of the alcohol with the starting ester would have been.
In other words, both reactions that occur in the presence of the tertiary amine are faster than the single
reaction that occurs in the absence of the tertiary amine.
N N
O
C
CH
3
OCH
3
+
O
C
CH
3
N N
+
CH
3
OH
+
ROH
O
C
CH
3
OR
+
N N
66.
a.
eq
=
K
CH
3
COOH + CH
3
CH
2
OH
CH
3
CO
2
CH
2
CH
3
+
H
2
O
[CH
3
CO
2
CH
2
CH
3
] [H
2
O]
[CH
3
COOH] [CH
3
CH
2
OH]
4 02
1
2 00
1
2 2
2
2
.
(
)
.
(
)
=
−
=
−
−
x
x
x
x
x
take the square root of both sides :
=
=
=
x
x
x
2 3
0 667 .
[ethyl acetate] = 0.667 times the concentration of acetic acid used
b.
4 02
10 1
4 02
11 10
4 02 11 10
3.02
2
2
2
2
2
2
.
(
(
.
. (
)
=
− −
=
− +
− + =
x
x
x
x
x
x
x
x
x
x
)
)
−
− =
44 22 4 02 0
.
.
x
x
x
solving for using the quadratic formula:
=
0 974 .
[ethyl acetate] = 0.974 tim
c.
4 02
100 1
0 997
2
.
(
(
.
=
− −
=
x
x
x
x
)
)
[ethyl acetate] = 0.997 times the concentration of acetic acid used