# 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 (${\rm{C{=}O}}$) bound to one alkyl (${-}{\rm {R}}$) fragment and one hydrogen atom, with ${\rm{RC({=}O)H}}$ or ${\rm{R{-}CHO}}$ 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 (${-}{\rm{COOH}}$)

### deprotonate

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

### enol

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