Illustrated Glossary of Organic Chemistry
MTBE:
Methyl
tert
-butyl
ether
.
IUPAC
name
2-
methoxy
-2-
methyl
propane
. A simple
aliphatic
ether
. Used until recently in California as a
gasoline
oxygenate to increase
octane rating
, until it was discovered that MTBE -- a suspect
carcinogen
at high concentrations -- was accumulating in municipal wells and other
water
sources. In the United States,
ethanol
has replaced MTBE as a fuel oxygenate.
Lewis structure
Ball and spoke
Space filling model
Molecular structure
of MTBE.
CH
3
OH
Acid catalyst
Industrial scale
synthesis
of MTBE involves
acid-catalyzed
electrophilic addition
of
methanol
to
isobutylene
(2-
methyl
propene
). This
addition reaction
obeys
Markovnikov's rule
.
Related terms:
Tetrahydrofuran
,
THF
,
tetrahydropyran
,
epoxide
,
oxirane
,
oxetane
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