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Adol Condensation of Dibenzalacetone
Adol Condensation of Dibenzalacetone
9/21/16
Professor Qi Li
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.