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Chapter 17 583
Copyright © 2017 Pearson Education, Inc.
b.
The reaction involves two successive aldol condensations.
O O
O
CH
O O
O
O
O
+
HO
−
HO
−
H
2
O
+
H
2
O
C
O
H
H
C
c.
The base removes a proton from the carbon that is flanked by two carbonyl groups; this is followed by
an intramolecular S
N
2 reaction.
O O
Br H
HO
−
O O
Br H
−
O O
+
Br
−
d.
A proton is removed from the
a
-carbon that is flanked by a carbonyl group and a nitrile; then an intra-
molecular S
N
2 reaction occurs.
O
C
N
Br
−
HO
−
O
C
N
O
O
C
N
Br
O
O
73.
−
O
LDA/THF
add slowly
O
O
_
O
O
O
how the reagents become connected
HCl
tautomerization
O
O
O
−
74.
a.
CH
3
CH
2
OH
1. Br
2
, PBr
3
2. H
2
O
CH
3
CH OH
Br
NH
3
CH
3
NH
4
CH O
+
− +
NH
3
excess
C
O
C
O
C
O
alanine