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Chapter 19 655
Copyright © 2017 Pearson Education, Inc.
5.
a.
C NCH
2
CH
2
CH
3
CH
3
c.
OH
b.
+
N
+
H H
N H
3
C
C
O
d.
C N
CH
2
CH
2
CH
3
CH
2
CH
3
6.
N
H
N
H
+
N
H
+
N
H
+
N
H
−
−
−
+
−
7.
Pyrrole and its conjugate base are both aromatic. Cyclopentadiene does not become aromatic until it loses
a proton. It is the drive for the nonaromatic compound to become a stable aromatic compound that causes
cyclopentadiene to be a stronger acid than pyrrole.
N
H
aromatic
N
aromatic
+
H
+
nonaromatic
aromatic
+
H
+
−
−
8.
N
H
D
N
H
N
H
D
+
H
D
2-deuteriopyrrole
OD
2
D
2
O
+
9.
Solved in the text.
10.
Pyridine will act as an amine with the alkyl bromide, forming a quaternary ammonium salt.
N
+
CH
3
CH
2
N
CH
2
CH
3
Br
−
+
Br