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8L Date finished:
Group No. 5
EXERCISE 9B
Synthesis of Dibenzalacetone by Aldol Condensation
I. Introduction
Aldol condensations are important in organic synthesis, providing a good way to form
carbon–carbon bonds. According to Mahrwald in 2004 An aldol condensation is an organic
reaction in which an enol or an enolate ion reacts with a carbonyl compound to form a β-
hydroxyaldehyde or β-hydroxyketone, followed by a dehydration to give a conjugated
enone. In its usual form, it involves the nucleophilic addition of a ketone enolate to an
aldehyde to form a β-hydroxy ketone, or "aldol" (aldehyde and alcohol), a structural unit
found in many naturally occurring molecules and pharmaceuticals (Wade, 2005). The
fundamental transformation in this reaction is a dimerization of an aldehyde (or ketone) to a
beta-hydroxy aldehyde (or ketone) by alpha C–H addition of one reactant molecule to the
carbonyl group of a second reactant molecule.
The reaction of an aldehyde with a ketone employing sodium hydroxide as the base
is an example of a mixed aldol condensation reaction. You will do a double mixed-aldol
condensation reaction between acetone and benzaldehyde. Acetone has α-hydrogens (on
both sides) and thus can be deprotonated to give a nucleophilic enolate anion. The aldehyde
carbonyl is much more electrophilic than that of a ketone, and therefore reacts rapidly with
the enolate producing a benzolacetone. To synthesize dibenzolacetone, another mole of
benzaldehyde will be used to undergo another aldol condensation.
Figure 2. BOOK
II.
III. Data
3. What side products do you expect in the reation? How is the formation of these products
avoided?
Benzaldehyde Acetone
Mass
No. of moles
Molar Ratio
Limiting Reagent :_____________________________________________________________________
Theoretical Mass : _____________________________________________________________________
Theoretical mass
% Recovery
Acetone
Benzaldehyde
Dibenzalacetone