Aldol condensation

What is the purpose of the Aldol condensation reaction?

A base-induced aldol reaction between an aromatic aldehyde with NO alpha H’s and a ketone with a single equivalent set of alpha H’s.

Draw the reaction of the Aldol condensation reaction

→Self-aldol product (highlight) means the same compound acts as nucleophile and electrophile

How are α-H’s exchangeable

→The high acidity of alpha H’s implies theyre replaceable with H’s or D’s from solvent

Describe O and C in carbonyl

O and C are basic and nucleophilic

→ O is more basic/electrophilic than C

→C is more nucleophilic than O

What makes carbonyls electrophiles (e^- acceptors)

→The polarization of C=O bond makes C (δ+) attractive to nucleophiles and the EN of O makes it easily accept neg charge.

→Nucleophilic addition is generally reversible

What is Enolate addition to Carbonyls?

-Intermolecular addition of an enolate to an aldehyde/ketone favors formation of the adduct with the nucleophilic carbon

What does enolizable mean?

→Enolizable means that the carbonyl has alpha H’s.

Explain mixed aldols, how do the carbonyls acts

How does aldehyde compare to ketones?

→Mixed aldol reaction: Where 2 different carbonyl compounds are used simultaneously in the reaction. If both have alpha H’s, then multiple products may be produced.

→Usually only one carbonyl will have alpha H’s so one acts as the enolate (nucleophile) and the other as an electrophile.

→Aldehydes are more electrophilic & react faster than ketones

Draw the mechanism of Benzalacetone reaction

-Dehydrated aldol products of benzaldehyde and acetone

Draw the mechanism of Benzalacetophenone reaction

-Dehydrated aldol products of benzaldehyde and acetophenone

Draw the flowchart of the benzalacetone reaction

Draw the flowchart of the benzalacetophenones reaction

Draw the 7 reagents