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Unsaturated Aldehydes and Ketones

A carbonyl group C=O and a conjugated C=C double bond influence each other, giving rise to different bonding and chemical properties.

Unsaturated carbonyl compounds

Electrostatic potential maps of ethylene, 1,3-butadiene and propenal: the C=C double bond of propenal has a low electron density

Bond Properties

Mechanism of 1,4 addition: nucleophilic attack on the β carbon, prototropy giving the enol and keto-enol equilibrium

Conjugate (Michael) Addition (1,4)

Robinson annulation: Michael addition of an enolate to an α,β-unsaturated ketone and intramolecular aldol condensation

Robinson Annulation