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Solvolysis
From Wikipedia, the free encyclopedia
Solvolysis is a special type of nucleophilic substitution or eliminiation 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.
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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 alcohols and amines; the hydrolysis of esters give alcohols and carboxylic acids.
An example of a solvolysis reaction would be the reaction with 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.
The reaction mechanism for this chemical reaction is an SN1 reaction.
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.
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- International Union of Pure and Applied Chemistry. "solvolysis". Compendium of Chemical Terminology Internet edition.