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Chapter 15 489
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c.
H
3
O
+
d.
H
3
O
+
if excess water is used; CH OH
3
+
2
if excess water is not used.
22.
The mechanism for the acid-catalyzed reaction of acetic acid and methanol is the exact reverse of the
mechanism for the acid-catalyzed hydrolysis of methyl acetate.
O
C
CH
3
OH
H B
+
O
C
CH
3
OH
+
H
+
CH
3
OH
OH
C
OCH
3
OH
CH
3
H
+
OH
C
OCH
3
OH
CH
3
H B
+
B
OH
C
OCH
3
OH
CH
3
+
O
C
CH
3
OCH
3
+
H
2
O
H B
O
C
CH
3
OCH
3
HB
+
+
H
23.
a.
+
b.
+
c.
HOCH
2
CH
2
CH
2
CH
2
OH
C
O
The mechanism for the hydrolysis of a cyclic ester
is the same as that for an acyclic ester.
24.
O
OH
OH
HO
OH
OH
HO
HO
+
+
O H
H B
+
H
2
O +
HB
+
+
B
OH
O H
B
H
HO
+
+
+
O
O
OH
HO
O
O
O
H B
+