MCAT Organic Chemistry Review 2018-2019

(singke) #1

Aldol Condensation


In  the aldol   condensation,   the aldehyde    or  ketone  acts    as  both    nucleophile and electrophile,
resulting in the formation of a carbon–carbon bond in a new molecule called an aldol.

An  aldol   contains    both    aldehyde    and alcohol functional  groups.
The nucleophile is the enolate formed from the deprotonation of the α-carbon.
The electrophile is the aldehyde or ketone in the form of the keto tautomer.
First, a condensation reaction occurs in which the two molecules come together.
After the aldol is formed, a dehydration reaction (loss of a water molecule) occurs. This results
in an α,β-unsaturated carbonyl.

Retro-aldol reactions   are the reverse of  aldol   condensations.

Retro-aldol reactions   are catalyzed   by  heat    and base.
In these reactions, the bond between an α- and β-carbon is cleaved.
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