Integrated SequencePhysics Chemistry Organic Biology

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Nucleophiles and Electrophiles

Reactions of Alcohols and Ethers

Reactions of Aldehydes and Ketones

In aldol condensation, the enolate serves as a nucleophile, with its α carbon attacking the electrophilic carbonyl carbon of the aldehyde or ketone form also present in solution. Aldol condensation straddles both of the big categories of reactions of aldehydes and ketones. It involves both nucleophilic attack at the carbonyl carbon and electrophilic attack at the α-carbon.

The product of aldol addition is a β-hydroxy aldehyde or ketone, which readily undergoes dehydration to yield an αβ-unsaturated aldehyde or ketone.

Reactions of Aldehydes and Ketones



Bioenergetics and Cellular Respiration

Aldol condensation is a very important reaction type for biochemistry. For example, in energy metabolism, the cleavage of the 1,6 phosphate diester of fructose in glycolysis is a retro-aldol reaction (aldol condensation in reverse). As another example from energy metabolism, the addition of oxaloacetate to acetyl CoA, which begins the citric acid cycle, is an aldol condensation. As an example from the wider biochemical context, the intramolecular covalent cross-links stabilizing collagen fibers are formed by an aldol condensation between aldehyde derivatives of lysine side chains. As you can imagine, aldol condensation is an MCAT favorite.

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