Chemistry Reference
In-Depth Information
10.60
O
O
O
O
CH
3
CH
2
OCCH
(
CH
2
)
3
COCH
2
CH
3
CH
3
CH
2
OCCH
(
CH
2
)
3
COCH
2
CH
3
-
+
H
-
O
CH
3
CH
2
-
O
CH
3
CH
2
O
O
-
OCH
2
CH
3
O
H
+
C
CH
3
CH
2
O C
2
CH
3
CH
2
O
O
O
O
O
H
C
-
C
CH
3
CH
2
O
+
CH
3
CH
2
OH
CH
3
CH
2
O
H
Deprotonation of the
β
-ketoester drives the equilibrium to the right. Neutralization of
the reaction mixture gives ethyl 2-oxocyclopentanecarboxylate.
10.61
The enolate of ethyl acetate behaves as a nucleophile and the nonenolizable ester,
ethyl benzoate, behaves as an electrophile.
O
O
CO
2
CH
2
CH
3
+CH
3
CH
2
OCCH
3
O
1.
NaOCH
2
CH
3
OCH
2
CH
3
+
2.
H O
3
10.62
Review Sec. 10.20.
The six atoms that lie in one plane are
_
O
C
H
+
N
C
H
