Solvolysis

Solvolysis

Solvolysis is a special type of nucleophilic substitution or elimination where the nucleophile is a solvent molecule. For certain nucleophiles, there are specific terms for the type of solvolysis reaction. For water, the term is hydrolysis; for alcohols, it is alcoholysis; for ammonia, it is ammonolysis.

Hydrolysis

While solvolysis often refers to an organic chemistry context, hydrolysis is very common in inorganic chemistry, where aqua complexes of metal ions react with solvent molecules due to the Lewis acidity 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 amides give carboxylic acids and amines; the hydrolysis of esters give alcohols and carboxylic acids.

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 esters 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.

Solvolysis of a chiral reactant results in the racemate (as expected in SN1) 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

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  • solvolysis — [säl väl′ə sis, sôlväl′ə sis] n. [< SOLVENT + O + LYSIS] a chemical interaction, as hydrolysis, between a solute and solvent, with the production of new compounds …   English World dictionary

  • solvolysis — solvolytic /sol veuh lit ik/, adj. /sol vol euh sis/, n. Chem. a chemical reaction in which the solvent and solute interact; lyolysis. [1920 25; < NL; see SOLVE, O , LYSIS] * * * ▪ chemistry       a chemical reaction in which the solvent, such as …   Universalium

  • solvolysis — solvolizė statusas T sritis chemija apibrėžtis Tirpinamos medžiagos ir tirpiklio reakcija bei susidariusio produkto skilimas. atitikmenys: angl. lyolysis; solvolysis rus. сольволиз …   Chemijos terminų aiškinamasis žodynas

  • solvolysis — noun Etymology: New Latin, from English solvent + New Latin o + lysis Date: 1916 a chemical reaction (as hydrolysis) of a solvent and solute that results in the formation of new compounds • solvolytic adjective …   New Collegiate Dictionary

  • solvolysis — noun any reaction, between a solute and its solvent, in which one or more bonds of the solute are broken; specifically a substitution, elimination or fragmentation reaction in which the solvent is the nucleophile See Also …   Wiktionary

  • solvolysis — The reaction of a dissolved salt with the solvent to form an acid and a base; the (partial) reverse of neutralization. If the solvent is water, an amphiprotic solvent, s. is called hydrolysis. * * * sol·vol·y·sis …   Medical dictionary

  • solvolysis — n. chemical process by which a solute and solvent form a new compound …   English contemporary dictionary

  • solvolysis — sol·vol·y·sis …   English syllables

  • solvolysis — sälˈväləsə̇s, sȯl noun Etymology: solvent + o + lysis : a chemical reaction of a solvent and a dissolved substance with the formation typically of one or two or more new compounds : either hydrolysis or an analogous reaction (as alcoholysis or… …   Useful english dictionary

  • SN1 reaction — The SN1 reaction is a substitution reaction in organic chemistry. SN stands for nucleophilic substitution and the 1 represents the fact that the rate determining step is unimolecular [ L. G. Wade, Jr., Organic Chemistry , 6th ed.,… …   Wikipedia

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