Solvolysis 1653289 209895688 2008-05-03T13:00:33Z 78.84.156.127 /* Hydrolysis */ '''Solvolysis''' is a special type of [[nucleophilic substitution]] or [[elimination reaction|elimination]] where the [[nucleophile]] is a [[solvent]] molecule. For certain nucleophiles, there are specific terms for the type of solvolysis reaction. For [[water (molecule)|water]], the term is [[hydrolysis]]; for alcohols, it is alcoholysis; for [[ammonia]], it is [[ammonolysis]]. ==Hydrolysis== {{main|hydrolysis}} While solvolysis often refers to an [[organic chemistry]] context, hydrolysis is very common in [[inorganic chemistry]], where aqua [[complex (chemistry)|complexes]] of metal ions react with solvent molecules due to the [[Lewis acid]]ity of the metal center. For example, aqueous solutions of [[aluminium chloride]] are acidic due to the aqua-aluminium complex losing protons to water molecules, giving [[hydronium ions]] which lowers the [[pH]]. In organic chemistry, hydrolysis reactions often give two fragments from an initial substrate. For example, the hydrolysis of [[amide]]s give [[carboxylic acid]]s and [[amine]]s; the hydrolysis of [[ester]]s give alcohols and [[carboxylic acid]]s. ==Alcoholysis== An example of a solvolysis reaction is the reaction of a [[triglyceride]] with a simple [[alcohol]] such as [[methanol]] or [[ethanol]] to give the methyl or ethyl [[ester]]s of the fatty acid, as well as [[glycerol]]. This reaction is more commonly known as a [[transesterification]] reaction due to the exchange of the alcohol fragments. The [[reaction mechanism]] for this [[chemical reaction]] is an [[SN1 reaction|S<sub>N</sub>1 reaction]]. Solvolysis of a [[chirality (chemistry)|chiral]] [[reactant]] results in the [[racemate]] (as expected in S<sub>N</sub>1) but is often accompanied by [[Walden inversion]]. This is explained by postulating an [[intimate ion pair]] whereby the leaving [[anion]] is still in proximity to the [[carbocation]] and effectively shielding it from an attack by the nucleophile. ==References== {{Unreferenced|date=October 2007}}<references/> ==External links== * {{GoldBookRef | file = S05762 | title = solvolysis}} [[Category:Substitution reactions]] [[ru:Сольволиз]]