Depto. Química Orgánica

CARBONYL COMPOUNDS:
REACTIVITY

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15/07/2017
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Reactivity of aldehydes and ketones
One of the most common reactions of an aldehyde or ketone is the attack of a electron-rich species on the electron-defficient carbonyl carbon.
Image Formaldehyde's LUMO
Lowest Unoccupied Molecular Orbital (LUMO) of formaldehyde, ready to accept electrons from the Highest Occupied Molecular Orbital (HOMO) of an electron-rich species. The attack will take place on carbon which bears the orbital highest coefficient.
Image Water addition to formaldehyde
Formaldehyde's carbon, initially planar with sp2 hybridization, suffers the attack of the electron cloud of water's oxygen. The reaction proceeds through a TS where the carbon turns into a tetrahedron, swapping its hybridization from sp2 to sp3.
The nucleophiles able to add to a carbonyl are quite diverse, with different synthetic consequences.
Nucleophilic Addition to Carbonyl
Agua y Alcoholes Water and Alcohols
Amoníaco, Aminas y Derivados Ammonia, Amines and Derivatives
Nucleófilos de Carbono Carbon Nucleophiles
Hidrógeno, Hidruros, Borano Hydrogen, Hydrides, Boranes
Reactions of Enols and Enolates
Halogenación Halogenation
Alquilación de enolatos Alkylation
Condensación Aldólica Aldol Condensation
Other Reactions
Oxidación Oxidation
Aldehídos y cetonas insaturados Unsaturated Aldehydes and Ketones