Chemistry Reference
In-Depth Information
13.3
Methoxide adds to C-4 followed by elimination of chloride ion.
-
CH
3
O
Cl
Cl
OCH
3
OCH
3
+Cl
-
N
N
-
N
13.4
The configuration of (+)-coniine is
R
(review Sec. 5.3).
13.5
(
S
-(-)-nicotine
N
H
C
H
3
N
The first equivalent of HCl reacts with the more basic,
sp
3
-hybridized nitrogen to give:
13.6
+
Cl
-
H
C
H
3
N
The second equivalent of HCl reacts with the
sp
2
-hybridized pyridine nitrogen:
Cl
-
+
2
H
C
H
3
+
N
H
13.7
The cation derived from protonation of pyrrole at C-2 is a hybrid of the following
resonance structures.
+
H
H
H
+
2
2
2
N
N
N
+
H
H
H
H
H
H
