Editing Hydrolysis (section)

===Alkaline hydrolysis===
Alkaline hydrolysis usually refers to types of [[nucleophilic substitution]] reactions in which the attacking [[nucleophile]] is a [[hydroxide ion]]. The best known type is [[saponification]]: cleaving [[ester]]s into [[carboxylate]] salts and [[Alcohol (chemistry)|alcohols]]. In [[ester hydrolysis]], the hydroxide ion nucleophile attacks the [[carbonyl]] carbon. This mechanism is supported by [[isotope labeling]] experiments. For example, when [[ethyl propionate]] with an [[oxygen-18]] labeled ethoxy group is treated with [[sodium hydroxide]] (NaOH), the oxygen-18 is completely absent from the [[sodium propionate]] product and is found exclusively in the [[ethanol]] formed.<ref name=mcmurry>{{cite book|last=McMurry|first=John|title=Organic Chemistry|year=1996|publisher=Brooks/Cole Publishing Company|location=Pacific Grove, CA|isbn=0534238327|pages=[https://archive.org/details/organicchemistry00mcmu/page/820 820–821]|edition=4th|url-access=registration|url=https://archive.org/details/organicchemistry00mcmu/page/820}}</ref>

:[[File:Nucleophilic Acyl Substitution with a Labeled Oxygen.png|Reacting isotopically labeled ethyl propionate with sodium hydroxide proves the proposed mechanism for nucleophilic acyl substitution.|563px]]

The reaction is often used to solubilize solid organic matter. [[Chemical drain cleaner]]s take advantage of this method to dissolve hair and fat in pipes. The reaction is also used to [[Alkaline hydrolysis (body disposal)|dispose of human and other animal remains]] as an alternative to traditional burial or cremation.