Chemistry Reference
In-Depth Information
15.
Write the steps in the mechanism for cleavage of an ether.
16.
Write an equation for the preparation of an epoxide from the corresponding alkene.
17.
Write equations for the reaction of ethylene oxide or other epoxides with
nucleophiles such as H
+
, and H
2
O, H
+
and alcohols, or a Grignard reagent.
18.
Write the steps in the mechanism for ring-opening reactions of ethylene oxide and
other epoxides.
ANSWERS TO PROBLEMS
Problems Within the Chapter
8.1
a.
ethyl isobutyl methyl ether or 1-ethoxy-2-methyl-propane
b.
phenyl
n
-propyl ether or 1-propoxybenzene or 1-phenoxypropane
c.
1-ethoxy-1-methylcyclohexane
8.2
a.
b.
O
c.
8.3
HOCH
2
CH
2
CH
2
CH
2
OH
1,4-butanediol
3-methoxy-1-propanol
CH
3
OCH
2
CH
2
CH
2
OH
CH
3
OCH
2
CH
2
OC H
3
1,2-dimethoxyethane
The compounds are listed in order of decreasing boiling point. The fewer the
hydroxyl groups, the fewer the possibilities there are for intermolecular hydrogen
bonding, and the lower the boiling point.
8.4
a.
b.
8.5
Yes. There are no acidic protons in the starting alkyl bromide.
8.6
We must first convert the alcohol to an alkyl halide before we can make the Grignard
reagent.
HBr or PBr
3
(CH
3
)
2
CHOH
(CH
3
)
2
CHBr
ether (dry)
Mg
D
2
O
(CH
3
)
2
CHMgBr
(CH
3
)
2
CHD
