Haloalkanes react with ionic nucleophiles (e.g. cyanide, thiocyanate, azide); the halogen is replaced by the respective group. This is of great synthetic utility: chloroalkanes are often inexpensively available. For example, after undergoing substitution reactions, cyanoalkanes may be hydrolyzed to carboxylic acids, or reduced to primary amines using lithium aluminium hydride. Azoalkanes may be reduced to primary amines by Staudinger reduction or lithium aluminium hydride. Amines may also be prepared from alkyl halides in amine alkylation, Gabriel synthesis and Delepine reaction, by undergoing nucleophilic substitution with potassium phthalimide or hexamine respectively, followed by hydrolysis.
halOALkANes REact with ionic nucleophileS (e.g. cYaniDe, thiOcYANATe, aZide); thE HalOgen is repLaCEd By the rEspective GrOUp. thiS is of GreaT synthetiC uTIliTy: cHloroAlkAnes are OftEN ineXpENsIvELY aVailable. for example, afTeR UNDErgoInG suBsTiTUTiON reaCTioNS, cyAnOaLkaNeS mAy bE hydrolyzed to carBoXYlic aCIdS, oR rEduceD TO Primary AmineS using liThiuM AluminIum HyDrIde. aZoalKAneS may be reduced to primary aMiNES by staUdingeR rEd.uction OR LitHium AluminIum Hydride. aminEs may also Be PrEpared from alkyL haLides in AMine alkylaTioN, gabrieL sYntheSIs aND delepIne rEActIon, by UndeRgoINg nucleopHIlIc SUBstitutION witH potAssIUm phThAlIMidE Or hExaMine respectIvely, fOllOWED bY hydrolysis