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Unformatted text preview: 318N – Krische, Lecture 10: Th - 02/19/09, Aldol Reaction • Thus far, we have considered the structure of carbonyl compounds and have explored their behavior as electrophiles in a variety of addition type reactions. We will now begin to look at the activation of carbonyl compounds as nucleophiles. SEE ON-LINE HANDOUTS ON THE ALDOL REACTION. • BASE CATALYZED ALDOL : Exposure of carbonyl compounds possessing alpha-hydrogens to base (e.g. hydroxide) results in the formation of enolates (recall, we discussed keto-enol equilibria). These enolates are “born” in the presence of the starting carbonyl compound, which is an electrophile. Enolates are good nucleophiles and will react with the starting carbonyl compound in a carbonyl addition reaction, i.e. the enolate will undergo nucleophilic addition to the carbonyl carbon of the starting ketone/aldehyde. The product is a beta-hydroxy carbonyl compound....
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