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Chapter 19 669
Copyright © 2017 Pearson Education, Inc.
e.
In the first step, hydroxide ion removes the most acidic hydrogen from the compound. A hydrogen
bonded to the C-4 methyl group is the most acidic hydrogen because the electrons left behind when
the proton is removed can be delocalized onto the positively charged nitrogen of the pyridine ring.
N
CH
3
CH
3
+
HO
−
N
CH
2
CH
3
+
−
H
2
C O
N
CH
2
CH
2
O
CH
3
+
−
HCl
N
CH
2
CH
2
OH
CH
3
+
N
H
+
CH
3
CH
2
MgBr
N
−
+
CH
3
CH
3
+
Mg
2
+
+
Br
−
f.
41.
NHNH
2
+
O C C
6
H
5
CH
3
NHN C C
6
H
5
CH
3
NH NH C C
6
H
5
CH
2
NH
CH
2
NH
H
NH
2
CH
2
C
C
6
H
5
NH
NH
2
CH
2
C
C
6
H
5
NH
2
+
NH
H
NH
2
C
6
H
5
B
NH
NH
2
C
6
H
5
H B
+
NH
NH
3
C
6
H
5
+
NH
C
6
H
5
H
+
NH
C
6
H
5
H B
+
B
+
B
H B
+
C
C
6
H
5