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 (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

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 CC {\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 C=CN{ \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 RMgX{\rm{R{-}MgX}}, where the halogen may be Cl{-}{\rm{Cl}} , Br{-}{\rm{Br}} , or I{-}{\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 C=NNHR{-}{\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 C=NH {\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 (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

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 π \pi bond (pi bond) while generating two new σ\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, SH{-}{\rm{SH}} , through CS {\rm{C{-}S}} bonds, with RSH {\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