Aim: To synthesize dibenzalacetone from benzaldehyde and acetone (Aldol condensation)

Theory:
The purpose of this experiment is to synthesis dibenzalacetone (trans, trans-1,5-diphenyl-
1,4-pentadien-3-one) through the aldol condensation of acetone with benzaldehyde. The
synthesis begins by using strong base to generate the acetone enolate ion. Water (not shown) is
formed as a byproduct. The equilbrium position of this reaction strongly favors the starting
acetone, and the amount of acetone enolate formed is quite small; however the enolate is
extremely nucleophilic

Being a very strong nucleophile, this enolate attacks the carbonyl of benzaldehyde and forms
a B-carbonyl alkoxide ion. This alkoxide ion abstracts a proton from water to form a beta
hydroxy ketone. Sodium hydroxide abstracts another acidic alpha H to form a stabilized
carbanion. The electron pair on carbon is used to eliminate the hyroxide ion, forming a alpha-
beta unsaturated ketone in an irreversible step. This is an example of an E1CB mechanism. Note
that in this reaction, the intermediate alcohol is dehydrated under basic conditions, unlike most
alcohol dehydrations, which are generally E1 mechanisms under acid conditions. The
E1CB mechanism is made possible by the presence of the carbonyl, which stabilizes the
intermediate carbanion.
Since this newly formed ketone still posses alpha hydrogens, it too can undergo the same enolate
condensation reaction with a second mole of benzaldehyde to form the final product:

Procedure:

Before you come into lab, make sure you have filled in your table of reagents and products. You
will need these values (particularly the molecular formula and molecular weight) to determine
the identify of your products and to calculate your final yield. Take care to determine the
coefficients of the balance chemical reaction when determining the theoretical yield. Finally, it
is important that you know exactly what you are going to be doing so you can work more
efficiently:
Pocedure:
1. Pipet into a 250mL Erlenmeyer flask the following quantities: 1.43g acetone and 5.25g
benzaldehyde (densities will be needed to determine the proper volumes). Note: it is
important to maintain a 1:2 molar ratio of acetone to benzaldehyde. You may have to
adjust your volumes accordingly.
2. Add a magnetic stirring bar to the Erlenmeyer flask and set the motor for the faster
stirring possible WITHOUT splatter.
 3. In a 100 mL beaker, thoroughly mix 20 mL of 6 M sodium hydroxide and 20 mL of 95%
ethanol.
4. Pour this mixture into the Erlenmeyer flask and adjust the stirrer motor to maintain
maximum stirring.
5. Continue to stir for an additional 15 minutes. Note any color changes that may occur.
6. Isolate the product by suction filtration and wash with COLD ethanol (remember: it
takes a while to cool the ethanol so plan ahead).
7. Continue the suction filtration for an additional 5-10 minutes to allow the product to air
dry.
8. Weigh the crude product and determine its melting point.
9. Recrystalize your product by dissolving it in 15 mL of ethyl acetate. Use low heat on
your hot plate and stir until all of the product dissolves. Stir in 15 mL of 95% ethanol
and remove from heat. Continue to stir constantly until crystals begin to form.
10. Collect the crystals by suction filtration and allow to air dry for 5-10 minutes.
11. Estimate the purity of your product using IR and melting point data

Conclusions:
Why does the acetone enolate preferentially attack the benzaldehyde rather than another
acetone molecule?
How does your IR compare to the literature IR?
How pure is your material? Is there any evidence that the purification steps were
effective?

Calculations
Density of acetone is 0.79 g/ml
So, 0.79 g will measure 1 ml
So, 1.43 g measures ??
1.43 X 1
=1.81 ml 2 ml
0.79

Density of benzaldehyde is 1.04 g/ml

So, 1.04 g will measure 1 ml
So, 5.25 g measures ???

5.25 X 1
=5.04 ml 5 m l
1.04