Name: Hasmaye Marie M.

Pinto Date performed:

Section: 3L Date finished:
Group No. 3

Exercise 9B
SYNTHESIS OF DIBENZALACTONE BY ALDOL CONDENSATION

I. INTRODUCTION
Dibenzalacetone and its importance
Dibenzylideneacetone or dibenzalacetone (abbreviated dba) is an organic
compound that is important in making suncreens. It has a chemical formula of C17H14O with
chemical structure

Dibenzalacetone
Pure dibenzalacetone is a pale-yellow solid that does not dissolve in water, but dissolves
in ethanol. This is because it’s a symmetrical, non-polar molecule. It is often used in organic
chemistry classes to show the reaction of a benzaldehyde and a ketone.

Aldol condensation and synthesis of dibenzalacetone

Aldol reactions or aldol condensation are one of the most important reactions in organic
chemistry (Perrin & Chang, 2016). Aldol reactions are fundamental in organic synthesis and
employed by synthetic chemists in carbon-carbon bond formation reactions of aldehydes and
ketones by creating a path for carbon-carbon bonds (Wang, 2010).
It occurs when aldehydes having α-hydrogen reacts with a dilute base and produces β-
hydroxy aldehydes called aldols. The general reaction for aldol condensation is:

Figure 1. General reaction of aldol condensation

 It is a nucleophilic addition where common bases such as NaOH or KOH are used. It
involves an aldehyde enolate acting as nucleophiles reacting with another molecule of the aldehyde
to form β-hydroxy aldehydes or aldehyde-alcohols (aldols).

Figure 2. Base-catalyzed aldol reaction

In the synthesis of dibenzalacetone, the reaction of an aldehyde with a ketone employing

sodium hydroxide as the base is an example of a mixed aldol condensation reaction.

Figure 3. Chemical equation for the synthesis of dibenzalacetone

Acetone having α-hydrogen on both sides is deprotonated and gives a nucleophilic enolate
anion. The alkoxide produced is protonated by the solvent producing β-hydroxyketone that
undergoes base-catalyzed dehydration. The full mechanism of the reaction is as follows:
 Figure 4. Mechanism for the synthesis of dibenzalacetone

The first step involves the deprotonation of the acetone to make an nucleophilic enolate.
The nucleophile attacks the electrophilic carbon of the benzaldehyde and forms and alkoxide. The
alkoxide will undergo protonation when it reacts with the solvent H2O and a neutral hydroxy-
ketone is produced in step three. The hydroxy-ketone deprotonates and another enolate is formed
(hydroxyenolate). When hydroxide is eliminated, an alkene pi bond is formed producing
benzalacetone. The benzalacetone attacks another benzaldehyde and forms a second β-
hydroxyketone. After the hydroxide leaves the second time forming another double bond, the final
product, dibenzalacetone, is generated.
OBJECTIVES:
In this laboratory exercise, the students are expected:
1. To synthesize dibenzalacetone from benzaldehyde and acetone;
2. To purify the synthesized dibenzalacetone using recrystallization;
3. To determine and compare the melting point of the crude and
recrystallized dibenzalacetone; and
4. To compare the product from the starting materials using simple
chemical test
 II. MATERIALS AND METHODS

A. Schematic Diagram of the Procedure

A.1 SYNTHESIS OF DIBENZALACETONE

Benzaldehyde

Put 1.25 ml into test tube

1.25ml
benzaldehyde

Add 0.40ml of acetone

Benzaldehyde + acetone in
a test tube

Add half of the

benzaldehyde + 10 ml of 95% ethanol in
acetone mixture (BA Erlenmeyer flask
mixture)
Add 12.50 ml water

Add 0.40ml 1.25 g NaOH

Ethanoic hydroxide solution in

Erlenmeyer flask

Half BA + Ethanoic
hydroxide solution
 Half BA + Ethanoic hydroxide solution in
Erlenmeyer flask

Add remaining BA mix after 10 mins

Rinse with small amount of 95% ethanol to transfer BA mix

Swirl the solution for 20 minutes

Suction filtration

Residue (solids) Filtrate

Wash three times with 10ml H2O followed by small amounts of ice-
cold ethanol

Crystals (products) in filter

paper

Press between two sheets of filter paper

Transfer in pre-weighed container

Crude dibenzalacetone in
pre-weighed container

Air dry

Weigh and determine

mass of yield
 A.1 RECRYSTALLIZATION OF DIBENZALACETONE AND MELTING POINT
DETERMINATION
A.2 CHARACTERIZATION OF DIBENZALACETONE
B. Setup (s)

Figure 1. Hot gravity filtration setup

Figure 2. Suction filtration setu

C. List of Necessary Chemicals
Chemical Structure Molar mass g.mol-1 Melting point °C Hazards Precautions Functions in the exercise

Sodium 40 318 Corrosive,

hydroxide alkaline

Ethanol 46 -114 Flammable

Benzaldehyde 106 -26 Irritant

Acetone 58 -95 Flammable,

harmful

Dibenzalacetone 234 110 Irritant

D. DATA

Table 1. Benzaldehyde-acetone mixture (BA mixture)

SAMPLE DESCRIPTION
Benzaldehyde

Mixture after
adding acetone

Table 2. Making of ethanoic hydroxide

SAMPLE DESCRIPTION
95% ethanol

Mixture after
adding water and
sodium
hydroxide

Table 3. Benzaldehyde-acetone mixture and ethanoic hydoxide

SAMPLE DESCRIPTION
Ethanoic
hydroxide + half
BA mixture
Mixture after 10
minutes with
remaining BA
mixture
Mixture after 20
minutes of
continuous
swirling
Table 4. Suction filtration of mixture
SAMPLE DESCRIPTION
Ethanoic
hydroxide + BA
Residue from the
mixture
Filtrate from the
mixture
Air dried crystals

Table 5. Data on the yield and percent recovery

weight of container + crystals, g ________________________

weight of container, g ________________________

weight of crystals, g ________________________

weight of container + recrystallize isolate, g ________________________

weight of container, g ________________________

weight of recrystallize isolate, g ________________________

percent recovery based, % ________________________

Table 6. Hot gravity filtration for recrystallization
SAMPLE DESCRIPTION
Dibenzacetone
crystals
Residue
Filtrate

Table 7. Suction filtration for recrystallization

SAMPLE DESCRIPTION
Sample after hot
gravity filtration
Residue from the
mixture
Filtrate from the
mixture
Recrystallized
air dried crystals

Table 8. Suction filtration of mixture

SAMPLE Temperature of Temperature of Temperature
initial melting initial melting range
Crude dibenzalacetone

Recrystallized
dibenzalacetone
Pure dibenzalacetone

Melting point of
dibenzalacetone in
literature
E. SAMPLE CALCULATION
F. REFERENCES

Perrin, C. L. & Chang, K. (2016). The Complete Mechanism of an Aldol

Condensation. The Journal of Organic Chemistry 81 (13) , 5631-5635. DOI:
10.1021/acs.joc.6b00959.

Wang, Z. (2010). Aldol Reaction and Aldol Condensation. In Comprehensive

Organic Name Reactions and Reagents, Z. Wang (Ed.).
doi:10.1002/9780470638859.conrr012
Swagata Mandal, Sangita Mandal, Sumanta K. Ghosh, Aniruddha Ghosh, Rumpa
Saha, Soujanya Banerjee & Bidyut Saha (2016). Review of the aldol reaction, Synthetic
Communications, 46:16,1327-1342, DOI: 10.1080/00397911.2016.1206938