Illustrated Glossary of Organic Chemistry
Retro-
aldol reaction
:
A reaction in which a
β
-
hydroxy
carbonyl
compound decomposes into an
aldehyde
or
ketone
, plus another
carbonyl
compound. The formal reverse of the
aldol reaction
.
+
HO
-
or
H
3
O
+
Aldol reaction
HO
-
or
H
3
O
+
Retro-
aldol reaction
Acetone
Acetophenone
β-Hydroxy ketone
In the presence of
acid catalysis
or
base catalysis
,
acetophenone
undergoes an
aldol reaction
with
acetone
, to give a
β-hydroxy ketone
product
. This
β-hydroxy ketone
can be decomposed back into
acetone
and
acetophenone
in a
base-catalyzed
(or
acid-catalyzed
) retro-
aldol reaction
.
Related terms:
Enolate
,
enol
,
tautomerization
,
Ph
,
arrows
,
aldol condensation
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