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Chapter 17 589
Copyright © 2017 Pearson Education, Inc.
82.
The middle carbonyl group is hydrated, because the hydrate is stabilized by the electron-withdrawing
carbonyl groups on either side of it.
O
O
O
O
O
N
H
2
NCHCO
O
R
+
imine
formation
CH C O
R
O
O
O
N CHR
+
CO
2
H O
H
O
O
N CHR
+
_
_
HO
O
O
NH
2
O
O
N
O
O
HO
H
O
O
N
O
−
O
O
O
O
imine
formation
+
H
3
O
+
−
−
O
O
+
H
2
O
OH
OH
imine
hydrolysis H
2
O
+
O
RCH
−
trace acid
trace acid
83.
C H
O H
O
C H
C H
O
CH
CH
2
OH
HO
−
O
−
−
O
H
2
O
CH
2
O
−
O
−
+
CO
−
O
HO
−
CO
−
O
+