Alpha Carbonyl Chemistry

Vocabulary

acid-catalyzed reaction

reaction that occurs under acidic conditions with a proton donor

aldehyde

organic compound that contains a carbonyl group (C=O{\rm{C{=}O}}) bound to one alkyl (R{-}{\rm {R}}) fragment and one hydrogen atom, with RC(=O)H{\rm{RC({=}O)H}} or RCHO{\rm{R{-}CHO}} stoichiometry

alpha carbon

carbon that is directly attached to the carbonyl group (on either side)

alpha proton

any proton (H+) joined to an alpha carbon

base-catalyzed reaction

reaction that occurs under basic conditions with a proton acceptor

carbonyl

functional group in which a carbon atom is double-bonded to an oxygen atom

carboxylic acid

compound that contains an alkyl or aryl group (R) attached to a carboxyl group (COOH{-}{\rm{COOH}})

deprotonate

to remove a hydrogen ion (H+) to form the conjugate base of a compound

enol

compound that has a C=C{\rm{C{=}C}} (-ene) bond as well as a hydroxyl (OH) group (-ol)

enol form

compound that has an alcohol in the equilibrium between a carbonyl and an enol

enolate

anion formed when an alpha hydrogen in the molecule of an aldehyde or a ketone is removed as a hydrogen ion

intramolecular proton transfer

single-step mechanistic process that moves a hydrogen atom from one atom within a molecule to another atom within the same molecule

keto form

compound that has a carbonyl in the equilibrium between a carbonyl and an enol

keto-enol tautomerism

chemical equilibrium between a ketone or aldehyde and an enol

ketone

organic compound that contains a carbonyl group (C=O{\rm{C{=}O}}) bound to two alkyl (R{-}{\rm {R}}) fragments, which can be the same (R and R) or different (R and R′) with RC(=O)R {\rm{RC({=}O)R'}} or RCOR′ stoichiometry

protonate

to add a hydrogen ion (H+) to form the conjugate acid of a compound

tautomer

one of two or more constitutional isomers that differ only in the placement of a single proton