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Copyright © 2017 Pearson Education, Inc.
CHAPTER 17
Reactions at the
A
-Carbon
Important Terms
acetoacetic ester synthesis
synthesis of a methyl ketone using ethyl acetoacetate as the starting material.
aldol addition
a reaction between two molecules of an aldehyde (or two molecules of a ketone)
that connects the
a
-carbon of one with the carbonyl carbon of the other.
aldol condensation
an aldol addition followed by elimination of water.
annulation reaction
a ring-forming reaction.
A
-carbon
a carbon adjacent to a carbonyl carbon.
carbon acid
a compound that contains a carbon bonded to a relatively acidic hydrogen.
Claisen condensation
a reaction between two molecules of an ester that connects the
a
-carbon of one
with the carbonyl carbon of the other and eliminates an alkoxide ion.
condensation reaction
a reaction combining two molecules while removing a small molecule (usually
water or an alcohol).
crossed aldol addition
an aldol addition using two different aldehydes or ketones.
crossed Claisen
a Claisen condensation using two different esters.
condensation
decarboxylation
loss of carbon dioxide.
Dieckmann condensation
an intramolecular Claisen condensation.
B
-diketone
a ketone with a second ketone carbonyl group at the
b
-position.
E1cB
a two-step elimination reaction that proceeds via a delocalized carbanion
intermediate.
enolization
keto–enol interconversion.
gluconeogenesis
the synthesis of d-glucose from pyruvate.
glycolysis
the breakdown of d-glucose into two molecules of pyruvate.
haloform reaction
the conversion of a methyl ketone to a carboxylic acid and haloform using Cl
2
(or Br
2
or I
2
) and HO
-
.
Hell–Volhard–Zelinski
the conversion of a carboxylic acid into an
a
-bromocarboxylic acid using
(HVZ) reaction
PBr
3
+
Br
2
.