Mohammad Bazrouk

9/21/16
Professor Qi Li

Adol Condensation of Dibenzalacetone

Purpose: The objective of the experiment is to synthesize and recrystallize Dibenzalacetone with
the use of sodium hydroxide as a base in reaction with the ketone group of benzaldehyde.
Condensation is prepared by acetone along with two equal moles of Benzaldehyde.
Observation and Explanation:
Adol condensation is a process in which two carbonyl groups are joined together with a loss of a
water molecule to form a hydroxyketone. The product is called an Adol because it possess an aldehyde
group and an alcohol group. In the first step, the sodium hydroxide was mixed with ethanol and gives a
noticeably exothermic reaction. The sodium hydroxide was used as a catalyst and a base in the reaction.
The ethanol serves as a solvent that allows the benzaldehyde and acetone to dissolve in solution and react
with one another. After mixing the solution color turns from clear liquid to yellow. After agitating the
mixture yellow solid precipitate form and color of solution is, egg yolk colored. The reaction mixture had
a noticeably fruity smell. At this point, the mixture contains side products and impurities. Use of
recrystallization can remove the impurities. The benzaldehyde and acetone mixture were added at
separate 15 minute intervals to prevent mono substitution of benzalacetone.

Discussion and Conclusion:

The final crude product weight was higher than expected with a mass of 5.2g. This could have
been caused by using slightly more benzaldehyde than the experiment called for with and +0.5ml
error analysis. On final analysis with the melting point as expected the crude product had a lower
melting point temperature with a range of 102-103C than the compared recrystallized product at
105-108C. The slightly lower melting temperature in my products tells me that there could still
be possible impurities or reaction was not taken completion due to inconsistent stirring during
the 15-minute interval. Some things that could have been better is adding a stirring rod so that
the reactants are being mixed consistently. Other possible ideas is keeping the reaction in ice to
lower temperature of overall reaction. After recrystallization a loss of about 1.4 grams was
observed. This may be due to some of the reaction being boiled away during the heating process
or being dissolved and lost in the ethanol.
Post Lab Questions:
1. Why is it important to maintain equivalent proportions of reagents in
this reaction?
2. What side products do you expect in this reaction? How are they
removed?

3. What evidence do you have that tells you the product is of a single geometric isomer or a
mixture of isomers? Does the melting point give you such information?
5. How would you change the procedures in this chapter if you wished to synthesize
benzalacetone? Benzalacetophenone?
1. The importance of keeping equivalent proportions of reagents is to get the desired di
substituted product. Stereo chemistry must be maintained to avoid by product formation of
benzalacetone. If too much benzaladehyde is added or too much acetone by product could form
because of imbalance in stereochemistry and could be difficult to remove despite
recrystallization.
2. Some side products of this reaction is benzalacetone from incomplete reaction of reagents.
Another side product is diacetone alcohol from acetone reacting with itself and then dehydration
of the hydroxyketone. Finally benzyl alcohol and benzoic acid from reaction with just sodium
hydroxide. These can all be removed from the mixture by recrystallization with ethanol.
3. A very sharp melting point and information about the final product tell me that my I should
have one pure geometric isomer which is trans conformation.
5. To create benzalacetone, one would repeat the same procedure but would decrease the amount
of benzaldehyde in the mixture so that acetone and benzaldehyde are present at a 1:1 mixture
instead of 2:1. This way there will only be one mole of benzaldehyde to react instead of two
which give the di substituted product. To create benzalacetophenone one would want to react
benzaldehyde with acetophenone instead of acetone and similarly to the above procedure use a
1:1 mixture with the same procedure.