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NaOH ? 2 eq 2 eq Ph Ph Ph Rh Ph Ph Ph. 0 A B. D

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empty.gifempty.gifAldol condensation of benzaldehyde and acetone : The reaction of an aldehyde with a ketone employing sodium hydroxide as the base is an example of a mixed aldol condensation reaction.

Acetone has α-hydrogens (on both
sides) and thus can be deprotonated to give a nucleophilic enolate anion. The aldehyde carbonyl
is much more electrophilic than that of a ketone, and therefore reacts rapidly with the enolate.
The alkoxide produced is protonated by solvent, giving a β-hydroxyketone, which undergoes
base-catalyzed dehydration. The elimination process is particularly fast in this case because the
alkene is stabilized by conjugation to not only the carbonyl but also the benzene.

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