Illustrated Glossary of Organic Chemistry
Bi
sulfate
:
(1) The
conjugate base
of
sulfuric acid
.
Sulfuric acid
is a strong
acid
(
p
K
a
= -9), so bi
sulfate
ion
is a weak
base
.
Deprotonation
of
sulfuric acid (H
2
SO
4
)
with
water (H
2
O)
produces
bi
sulfate
ion
(HOSO
3
-
; shown in red) and
hydronium ion (H
3
O
+
)
.
Protonation
of
sulfate ion (SO
4
2-
)
with
hydronium ion (H
3
O
+
)
produces
bi
sulfate
ion
(HOSO
3
-
; shown in red) and
water (H
2
O)
.
(2) An
ester
of
sulfuric acid
in which only one
sulfuric acid
hydroxyl group
has been
esterified
. The
product
of
esterification
of both
sulfuric acid
hydroxyl groups
is a
sulfate
ester
.
Methyl
bi
sulfate
(CH
3
OSO
3
H) can be
produced
by
esterification
of one
hydroxyl group
of
sulfuric acid (H
2
SO
4
)
with
methanol (CH
3
OH)
.
Esterification
of the second
hydroxyl group
produces
methyl
sulfate
, (CH
3
O)
2
SO
2
.
Related terms:
Resonance
,
conjugate acid
,
Bronsted acid
,
Bronsted-Lowry acid
,
Bronsted base
,
Bronsted-Lowry base
,
curved arrow
,
arrows
,
oxyanion
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