Chemistry Reference
In-Depth Information
8.42
a.
Add each compound to a small amount of 10% aqueous sodium hydroxide.
The phenol dissolves, whereas the ether is inert toward the base.
Na
+
-
-
Na
+
OH
+
OH
O
+H
2
Na
+
-
OCH
3
+
OH
no reaction
b.
Add a small piece of sodium to each compound. The alcohol liberates a gas
(hydrogen), whereas no gas bubbles are apparent in the ether.
2 CH
3
CH
2
CH
2
CH
2
O
_
Na
+
H
2
2 Na
+
2 CH
3
CH
2
CH
2
CH
2
OH
+
no reaction
Na
CH
3
OCH
2
CH
2
CH
3
+
c.
In separate test tubes, add a little of each compound to concentrated sulfuric
acid. The ether is protonated and dissolves, whereas the hydrocarbon, being
inert and less dense than sulfuric acid, simply floats on top.
d.
Add a little bromine in carbon tetrachloride to each ether. The allyl phenyl
ether, being unsaturated, quickly decolorizes the bromine, but the ethyl
phenyl ether does not.
H
2
C
CHC H
2
OC
6
H
5
+
Br
2
H
2
C
Br
CHCH
2
OC
6
H
5
Br
no reaction
CH
3
CH
2
OC
6
H
5
+ r
2
