Chemistry Reference
In-Depth Information
6.3
Use Figure 6.1 as a guide:
H
H
_
_
δ
δ
NC
C
Br
CH
2
CH
3
transition state
ENERGY
E
a
CH
3
CH
2
CH
2
Br + NaCN
ΔΗ
CH
3
CH
2
CH
2
CN + NaBr
REACTION COORDINATE
6.4
a.
-
C
N
+ r
-
CH
3
Br
H
3
C
CN
Note:
trans
cis
b.
C
H
3
C
H
3
-
C
Note: inversion
N
+ r
-
CH
3
CH
2
C
C
CH
2
CH
3
Br
H
NC
H
c.
6.5
CH
3
CH
2
CH
2
CH
2
Br > (CH
3
)
2
CHCH
2
Br > CH
3
CH
2
CH(CH
3
)Br
The more crowded the carbon where displacement occurs, the slower the reaction
rate.
6.6
The reaction takes place via an S
N
1 mechanism because the substrate is a tertiary
halide. The expected product is
tert
-butyl methyl ether. The reaction energy diagram
resembles that for the S
N
1 reaction shown in Figure 6.2:
