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Organic Chemistry (CH 238) Synthesis Of Dibenzalacetone

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Sandra Watson
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Aldol Condensation and Synthesis of Dibenzalacetone

Course

Organic Chemistry II Lab (CH 238)

University

University of Alabama at Birmingham

2
Introduction
Aldol condensations play a vital role in organic synthesis due to their ability to form
carbon-carbon bonds. Aldol condensation begins by forming an enolate anion, which is produced
from either an aldehyde or a ketone. Due to resonance stability, enolate anions are able to act as a
nucleophile. The nucleophilic enolate anion attacks the electrophilic carbonyl carbon of an
aldehyde or ketone, forming a α,β-unsaturated carbonyl compound.1
Aldol reactions may be acid-catalyzed or base-catalyzed, although base catalysis occurs
more often. In base-catalyzed mechanisms, the enolate anion attaches to the carbonyl group
through nucleophilic addition, creating the tetrahedral carbonyl intermediate.2
The present experiment utilizes base-catalyzed aldol condensation to produce
dibenzalacetone, shown as figure 1.

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Organic Chemistry (CH 238) Synthesis Of Dibenzalacetone

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