Keto-enol tautomerization enolization “normal” aldehydes and ketones K eq = ~ 10 -8.

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Presentation transcript:

Keto-enol tautomerization enolization “normal” aldehydes and ketones K eq = ~ 10 -8

Stabilized aldehydes and ketones  -diketones K eq = ~ 10

Mechanism for acid-catalyzed enolization

Reactions of enols:  -halogenation

An example

Mechanism of  -halogenation

 -Bromination of Acids: the HVZ Reaction

The HVZ Reaction

Acidity of carbonyl compounds enolate ion formation pK a = ~ 16-20

Base-catalyzed enolization

Ester Enolates pK a = ~22

Alkylation of ester enolates

Reactions of enolates: The Aldol Condensation

Aldol Condensation

More Aldol Condensation

Formation of  -unsaturated carbonyls

An example

Claisen-Schmidt condensation

Examples

Nucleophilic Addition to  -Unsaturated Carbonyls

Michael Addition

Robinson Annulation

Michael Addition

Robinson Annulation

The Claisen condensation

An example

The product

Another example

Another product

The Dieckmann condensation

Decarboxylation of Malonic Acids and b-Ketoacids Malonic acidAcetoacetic acid

Decarboxylation of Malonic Acids and b-Ketoacids

Ketone acylation using esters

Acetoacetic ester synthesis of ketones ethyl acetoacetate

Acetoacetic ester synthesis of ketones

Malonic ester synthesis of acids

diethyl malonate

Malonic ester synthesis of acids

Malonic ester synthesis examples

Michael addition

Wait! There’s more!

Th-th-that’s all, folks.

I lied - some cool biochemistry acetyl CoAmalonyl CoA

More cool stuff

Even more

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