Chemistry Reference
In-Depth Information
O
-
K
+
(
CH
3
)
3
C
CH
2
Br
+
(
CH
3
)
3
C
O
H
+
KBr
Dehydrohalogenation of 1-bromo-1-methylcyclohexane with a strong base (NaOH or
potassium
tert
-butoxide) would also provide the desired alkene. This reaction,
however, would be complicated by the formation of methylcyclohexene as the major
product.
6.28
This type of reaction sequence is a useful method for constructing C
−
C bonds.
a.
NH
3
Na
+
2
-
Na
+
H
3
C
C
CH
+
H
3
C
C
C
+
S
N
2
CH
2
C
C
CH
3
CH
2
Br
b.
NaNH
2
CH
3
Br
-
Na
+
H
C
CH
+
H
C
C
HC
3
C
CH
NH
3
NaNH
2
NH
3
CH
3
CH
2
Br
C
-
Na
+
C
H
3
C
CC
2
C
C
H
3
C
3
The order in which the alkyl halides were used could be reversed, with the
same overall result.
CH
3
CH
2
CH
2
Br
6.29
a.
NaNH
2
NH
3
_
Na
+
CH
3
CH
2
CC
CH
3
CH
2
CC
CH
2
CH
2
CH
3
H
2
Lindlar's catalyst
CH
3
CH
2
CCH
H
H
CH
3
CH
2
CH
2
CH
2
CH
3
b.
Na
+
-
H
2
Pt
OH
H
2
C
CHCH
2
Br
H
2
C
CHCH
2
OH
CH
3
CH
2
CH
2
OH
6.30
This base-induced elimination would proceed by an anti-periplanar E2 elimination, so
a H would be attacked by the base and then a leaving group would be lost.
HCFC-123
F
Cl
_
F
H
_
B
F
+ -H+F
Cl
F
Cl
F
Cl
HFC-134a
F
H
_
F
_
H
F
B
+ -H+F
F
F
F
F
H
