What side products are formed in the aldol condensation of dibenzalacetone?

1 Answer
Dec 14, 2015

Dibenzalacetone does not undergo the aldol condensation.


However, dibenzalacetone is formed by a crossed aldol condensation between benzaldehyde and acetone.


Some of the side products expected in this reaction could be:

1. Benzalacetone

From incomplete condensation of the benzaldehyde.

2. Diacetone alcohol (4-hydroxy-4-methylpentan-2-one) and mesityl oxide (4-methylpent-3-en-2-one)

From the aldol condensation of acetone with itself, followed by dehydration of the β-hydroxyketone.

#2"CH"_3"COCH"_3 → underbrace(("CH"_3)_2"C(OH)CH"_2"COCH"_3)_color(red)("diacetone alcohol") → underbrace(("CH"_3)_2"C=CHCOCH"_3)_color(red)("mesityl oxide") #

3. Benzyl alcohol and benzoic acid from the Cannizzaro reaction of benzaldehyde.