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566 Chapter 17
Copyright © 2017 Pearson Education, Inc.
30.
CH
3
CH
2
O
OCH
2
CH
3
CH
CH
3
a.
b.
H
OCH
3
CH
CH
2
CH
3
C
O
C
O
C
O
C
O
31.
a.
Only one carbonyl compound has
a
-hydrogens, so the one with
a
-hydrogens is added slowly to a
basic solution of the one without
a
-hydrogens.
1.
CH
3
O OCH
3
+
CH
3
O
−
C
O
CH
3
O
C
2. HCl
add slowly
CH
2
OCH
3
C
O
C
O
b.
Both carbonyl compounds have
a
-hydrogens, so LDA is used to form the enolate, and the other
carbonyl compound is added slowly.
1.
CH
3
OCH
3
C
O
add slowly
2. HCl
O
C
CH
3
O
C
CH
2
LDA
THF
−
CH
2
CH
3
C
O
C
O
c.
Only one carbonyl compound has
a
-hydrogens, so the one with
a
-hydrogens is added slowly to a
basic solution of the one without
a
-hydrogens.
1.
H OCH
3
+
CH
3
O
−
C
O
CH
3
O
C
2. HCl
add slowly
CH
2
H
C
O
C
O
32.
CH
3
O
−
+
CH
3
OH
COCH
3
OCH
3
O
−
O
COCH
3
O
O
CH
3
O
−
+
OCH
3
O
H
OCH
3
O
a 1,7-diester
_
OCH
3
O
OCH
3
O
33.
OH
CH
3
CCH
3
O
a.
b.
OH
CH
3
O