509 / 912
Chapter 15 501
Copyright © 2017 Pearson Education, Inc.
If the reaction formed a tetrahedral intermediate, some of the ester would not be isotopically labeled
because some of the label would have been transferred to hydroxide ion.
C
OCH
2
CH
3
18
18
18
18
18
18
18
HO
HO
H 2 O
H 2 O
–
OH
C OCH
2
CH
3
+
C
+ CH
3
CH
2
O
OH
OH
OH
O
–
O
C OCH
2
CH
3
OH
C OCH
2
CH
3
O
–
OH
18
O
C
OH +
O
C
CH
3
CH
2
O
–
O + CH
3
CH
2
OH
δ
–
δ
–
O
–
OH
C
OCH
2
CH
3
unlabeled ester
+
O
–
–
–
63.
a.
1, 3, 4, 6, 7, 9 will not form the indicated products under the given conditions.
b.
9 will form the product shown in the presence of an acid catalyst.
64.
Notice that in order to maximize the substitution product, a poor nucelophile is used for the substitution
reaction of the alkyl halide.
Br
Br
2
CH
3
CH
3
2
h
v
OCCH
3
H
O
OH
HCl
O
NaOCl
COO
–
COOH
O
O ºC
65.
The tertiary amine is a better nucleophile than the alcohol,
so formation of the amide with a positively charged nitrogen will be faster than formation of the new ester
would have been.
The positively charged amide is more reactive than an ester,