Date performed:

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.

Figure 1. formation of enolate ion

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

1. What is the role of sodium hydroxide in the reaction?

2. What are the structure structure requirements for aldol condensation?

3. What side products do you expect in the reation? How is the formation of these products
avoided?

Table 1. Melting point determination

Melting point
Crude dibenzalacetone
Recrystallized dibenzalacetone

Table 2. Yield of product

Mass of watch Mass of watch
Theoretical Mass
glass and filter glass, filter paper Mass of product % Yield
of product
paper and product

Molar Ratio: __________________________________________________________________________

Benzaldehyde Acetone
Mass
No. of moles
Molar Ratio
Limiting Reagent :_____________________________________________________________________
Theoretical Mass : _____________________________________________________________________

Table 3. Percent recovery after recrystallization

Mass of recrystallized sample

Theoretical mass

% Recovery

Table 4. Observation recorded for reaction steps

Steps Observations
Mixture of Reactants
Collection of crude product
by suction filtration
Collection of pure product
after recrystallization

Table 5. Characterization of Dibenzaldehyde

Iodoform Test -/+ Tollen’s Test -/+

Acetone
Benzaldehyde
Dibenzalacetone

IV. Sample Calculations

Mass = density X volume
No. of moles = Mass X Molar Mass
Theoretical yield = Molar Ratio of Limiting reagent X Molar Mass of Benzalacetone
%Yield = actual yield/theoretical yield x 100%
% recovery = (pure/impure) x 100