# Reactions of Aldehydes and Ketones

## Vocabulary

### acetal

organic compound characterized by the grouping C(OR)2, where R is an alkyl and is obtained by heating an aldehyde or a ketone with an alcohol

### 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

### alkoxide

conjugate base of an alcohol that consists of an organic group bonded to a negatively charged oxygen atom

### Baeyer-Villiger oxidation

reaction using peroxy acids or peroxides as the oxidant that cleaves the ${\rm{C{-}C}}$ bond next to a carbonyl, converting aldehydes to carboxylic acids and ketones to esters

### carbonyl

functional group in which carbon atoms are double bonded to oxygen atoms

### cyanohydrin

functional group containing both cyano and hydroxyl groups

### desulfurization

removal of sulfur from sulfur-containing compounds

### electronic effect

influence on the reactivity of a group based on movement or location of electrons in a bond

### electrophile

molecule or ion that accepts electrons to form a covalent bond

### enamine

amino group containing the double-bond linkage ${ \rm{C{=}C{-}N}}$

### Grignard reaction

reaction of a Grignard reagent with a carbonyl-containing compound to yield either an alcohol or another (different) carbonyl

### Grignard reagent

reagent that has the formula ${\rm{R{-}MgX}}$, where the halogen may be ${-}{\rm{Cl}}$, ${-}{\rm{Br}}$, or ${-}{\rm {I}}$

### hemiacetal

organic compound characterized by the grouping C(OH)(OR), where R is an alkyl group and is usually formed as an intermediate in the preparation of an acetal from an aldehyde or ketone

### hydrate

compound formed by the union of water with some other substance

### hydrazone

compound containing the group ${-}{\rm {C{=}NNHR}}$ formed by the action of hydrazine or a substituted hydrazine (such as phenylhydrazine) on a carbonyl-containing compound

### imine

organic compound containing the ${\rm {C{=}NH}}$ group or its substituted form NR that is derived from ammonia by replacement of two hydrogen atoms by a hydrocarbon group or other nonacid organic group

### 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

### nucleophile

molecule or ion rich in electrons that donates a pair of electrons that forms a covalent bond

### nucleophilic addition reaction

reaction where an electron-rich reactant (a nucleophile) reacts with an electron-deficient part of a compound. This reaction breaks one $\pi$ bond (pi bond) while generating two new $\sigma$ bonds (sigma bonds).

### protecting group

modified functional group that is unaffected by some reagents but easily removed by other reagents

### Raney nickel

catalyst for the hydrogenation of organic compounds that consists of an alloy of equal parts nickel and aluminum in the form of a pyrophoric powder or crystals or a suspension in alcohol

### steric effect

nonbonding interaction that occurs through 3-D space and changes the reactivity of an ion or molecule because of size, arrangement, and spatial factors

### thioacetal

sulfur analog of an acetal; an organic compound characterized by the grouping C(SR)2, where R is an alkyl and is obtained by heating an aldehyde or a ketone with a thiol

### thiol

organic compound that is derived from H2S. It contains an alkyl or aryl group covalently linked to a sulfhydryl group, ${-}{\rm{SH}}$, through ${\rm{C{-}S}}$ bonds, with ${\rm{R{-}SH}}$ stoichiometry.

### Wolff-Kishner reduction

reduction of a ketone or aldehyde to an alkane by conversion to a hydrazone followed by the addition of a strong base

### ylide

species with opposite formal charges on adjacent atoms