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class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>Polysaccharides</span> </div> </a> <ul id="toc-Polysaccharides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-DNA" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#DNA"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.5</span> <span>DNA</span> </div> </a> <ul id="toc-DNA-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metal_aqua_ions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metal_aqua_ions"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.6</span> <span>Metal aqua ions</span> </div> </a> <ul id="toc-Metal_aqua_ions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mechanism_strategies" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mechanism_strategies"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.7</span> <span>Mechanism strategies</span> </div> </a> <ul id="toc-Mechanism_strategies-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Catalysis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Catalysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Catalysis</span> </div> </a> <button aria-controls="toc-Catalysis-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Catalysis subsection</span> </button> <ul id="toc-Catalysis-sublist" class="vector-toc-list"> <li id="toc-Acidic_hydrolysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acidic_hydrolysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Acidic hydrolysis</span> </div> </a> <ul id="toc-Acidic_hydrolysis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Alkaline_hydrolysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Alkaline_hydrolysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Alkaline hydrolysis</span> </div> </a> <ul id="toc-Alkaline_hydrolysis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Hydrolysis</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 71 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-71" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">71 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AA%D8%AD%D9%84%D9%84_%D9%85%D8%A7%D8%A6%D9%8A" title="تحلل مائي – Arabic" lang="ar" hreflang="ar" data-title="تحلل مائي" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Hidr%C3%B3lisis" title="Hidrólisis – Asturian" lang="ast" hreflang="ast" data-title="Hidrólisis" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Hidroliz" title="Hidroliz – Azerbaijani" lang="az" hreflang="az" data-title="Hidroliz" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%86%E0%A6%B0%E0%A7%8D%E0%A6%A6%E0%A7%8D%E0%A6%B0_%E0%A6%AC%E0%A6%BF%E0%A6%B6%E0%A7%8D%E0%A6%B2%E0%A7%87%E0%A6%B7%E0%A6%A3" title="আর্দ্র বিশ্লেষণ – Bangla" lang="bn" hreflang="bn" data-title="আর্দ্র বিশ্লেষণ" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-ba mw-list-item"><a href="https://ba.wikipedia.org/wiki/%D0%93%D0%B8%D0%B4%D1%80%D0%BE%D0%BB%D0%B8%D0%B7" title="Гидролиз – Bashkir" lang="ba" hreflang="ba" data-title="Гидролиз" data-language-autonym="Башҡортса" data-language-local-name="Bashkir" class="interlanguage-link-target"><span>Башҡортса</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%93%D1%96%D0%B4%D1%80%D0%BE%D0%BB%D1%96%D0%B7" title="Гідроліз – Belarusian" lang="be" hreflang="be" data-title="Гідроліз" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A5%D0%B8%D0%B4%D1%80%D0%BE%D0%BB%D0%B8%D0%B7%D0%B0" title="Хидролиза – Bulgarian" lang="bg" hreflang="bg" data-title="Хидролиза" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Hidroliza" title="Hidroliza – Bosnian" lang="bs" hreflang="bs" data-title="Hidroliza" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Hidr%C3%B2lisi" title="Hidròlisi – Catalan" lang="ca" hreflang="ca" data-title="Hidròlisi" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Hydrol%C3%BDza" title="Hydrolýza – Czech" lang="cs" hreflang="cs" data-title="Hydrolýza" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Hydrolyse" title="Hydrolyse – Danish" lang="da" hreflang="da" data-title="Hydrolyse" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Hydrolyse" title="Hydrolyse – German" lang="de" hreflang="de" data-title="Hydrolyse" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/H%C3%BCdrol%C3%BC%C3%BCs" title="Hüdrolüüs – Estonian" lang="et" hreflang="et" data-title="Hüdrolüüs" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A5%CE%B4%CF%81%CF%8C%CE%BB%CF%85%CF%83%CE%B7" title="Υδρόλυση – Greek" lang="el" hreflang="el" data-title="Υδρόλυση" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Hidr%C3%B3lisis" title="Hidrólisis – Spanish" lang="es" hreflang="es" data-title="Hidrólisis" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Hidrolizo" title="Hidrolizo – Esperanto" lang="eo" hreflang="eo" data-title="Hidrolizo" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Hidrolisi" title="Hidrolisi – Basque" lang="eu" hreflang="eu" data-title="Hidrolisi" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A2%D8%A8%DA%A9%D8%A7%D9%81%D8%AA" title="آبکافت – Persian" lang="fa" hreflang="fa" data-title="آبکافت" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Hydrolyse" title="Hydrolyse – French" lang="fr" hreflang="fr" data-title="Hydrolyse" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Hidreal%C3%BA" title="Hidrealú – Irish" lang="ga" hreflang="ga" data-title="Hidrealú" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Hidr%C3%B3lise" title="Hidrólise – Galician" lang="gl" hreflang="gl" data-title="Hidrólise" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EA%B0%80%EC%88%98%EB%B6%84%ED%95%B4" title="가수분해 – Korean" lang="ko" hreflang="ko" data-title="가수분해" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%80%D5%AB%D5%A4%D6%80%D5%B8%D5%AC%D5%AB%D5%A6" title="Հիդրոլիզ – Armenian" lang="hy" hreflang="hy" data-title="Հիդրոլիզ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%9C%E0%A4%B2%E0%A5%80%E0%A4%AF_%E0%A4%B5%E0%A4%BF%E0%A4%B6%E0%A5%8D%E0%A4%B2%E0%A5%87%E0%A4%B7%E0%A4%A3" title="जलीय विश्लेषण – Hindi" lang="hi" hreflang="hi" data-title="जलीय विश्लेषण" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Hidroliza" title="Hidroliza – Croatian" lang="hr" hreflang="hr" data-title="Hidroliza" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Hidrolizo" title="Hidrolizo – Ido" lang="io" hreflang="io" data-title="Hidrolizo" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Hidrolisis" title="Hidrolisis – Indonesian" lang="id" hreflang="id" data-title="Hidrolisis" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Idrolisi" title="Idrolisi – Italian" lang="it" hreflang="it" data-title="Idrolisi" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%94%D7%99%D7%93%D7%A8%D7%95%D7%9C%D7%99%D7%96%D7%94" title="הידרוליזה – Hebrew" lang="he" hreflang="he" data-title="הידרוליזה" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%B0%E1%83%98%E1%83%93%E1%83%A0%E1%83%9D%E1%83%9A%E1%83%98%E1%83%96%E1%83%98" title="ჰიდროლიზი – Georgian" lang="ka" hreflang="ka" data-title="ჰიდროლიზი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%93%D0%B8%D0%B4%D1%80%D0%BE%D0%BB%D0%B8%D0%B7" title="Гидролиз – Kazakh" lang="kk" hreflang="kk" data-title="Гидролиз" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ht mw-list-item"><a href="https://ht.wikipedia.org/wiki/Idwoliz" title="Idwoliz – Haitian Creole" lang="ht" hreflang="ht" data-title="Idwoliz" data-language-autonym="Kreyòl ayisyen" data-language-local-name="Haitian Creole" class="interlanguage-link-target"><span>Kreyòl ayisyen</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%93%D0%B8%D0%B4%D1%80%D0%BE%D0%BB%D0%B8%D0%B7" title="Гидролиз – Kyrgyz" lang="ky" hreflang="ky" data-title="Гидролиз" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Hydrolysis" title="Hydrolysis – Latin" lang="la" hreflang="la" data-title="Hydrolysis" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Hidrol%C4%ABze" title="Hidrolīze – Latvian" lang="lv" hreflang="lv" data-title="Hidrolīze" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Hidroliz%C4%97" title="Hidrolizė – Lithuanian" lang="lt" hreflang="lt" data-title="Hidrolizė" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Hidrol%C3%ADzis" title="Hidrolízis – Hungarian" lang="hu" hreflang="hu" data-title="Hidrolízis" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A5%D0%B8%D0%B4%D1%80%D0%BE%D0%BB%D0%B8%D0%B7%D0%B0" title="Хидролиза – Macedonian" lang="mk" hreflang="mk" data-title="Хидролиза" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%9C%E0%B4%B2%E0%B4%B5%E0%B4%BF%E0%B4%B6%E0%B5%8D%E0%B4%B2%E0%B5%87%E0%B4%B7%E0%B4%A3%E0%B4%82" title="ജലവിശ്ലേഷണം – Malayalam" lang="ml" hreflang="ml" data-title="ജലവിശ്ലേഷണം" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Hidrolisis" title="Hidrolisis – Malay" lang="ms" hreflang="ms" data-title="Hidrolisis" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%93%D0%B8%D0%B4%D1%80%D0%BE%D0%BB%D0%B8%D0%B7" title="Гидролиз – Mongolian" lang="mn" hreflang="mn" data-title="Гидролиз" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Hydrolyse" title="Hydrolyse – Dutch" lang="nl" hreflang="nl" data-title="Hydrolyse" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E5%8A%A0%E6%B0%B4%E5%88%86%E8%A7%A3" title="加水分解 – Japanese" lang="ja" hreflang="ja" data-title="加水分解" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Hydrolyse" title="Hydrolyse – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Hydrolyse" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Idrolisi" title="Idrolisi – Occitan" lang="oc" hreflang="oc" data-title="Idrolisi" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Gidroliz" title="Gidroliz – Uzbek" lang="uz" hreflang="uz" data-title="Gidroliz" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-nds mw-list-item"><a href="https://nds.wikipedia.org/wiki/Hydrolyys" title="Hydrolyys – Low German" lang="nds" hreflang="nds" data-title="Hydrolyys" data-language-autonym="Plattdüütsch" data-language-local-name="Low German" class="interlanguage-link-target"><span>Plattdüütsch</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Hydroliza" title="Hydroliza – Polish" lang="pl" hreflang="pl" data-title="Hydroliza" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Hidr%C3%B3lise" title="Hidrólise – Portuguese" lang="pt" hreflang="pt" data-title="Hidrólise" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Reac%C8%9Bie_de_hidroliz%C4%83" title="Reacție de hidroliză – Romanian" lang="ro" hreflang="ro" data-title="Reacție de hidroliză" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%93%D0%B8%D0%B4%D1%80%D0%BE%D0%BB%D0%B8%D0%B7" title="Гидролиз – Russian" lang="ru" hreflang="ru" data-title="Гидролиз" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Hidroliza" title="Hidroliza – Albanian" lang="sq" hreflang="sq" data-title="Hidroliza" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Hydrolysis" title="Hydrolysis – Simple English" lang="en-simple" hreflang="en-simple" data-title="Hydrolysis" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Hydrol%C3%BDza" title="Hydrolýza – Slovak" lang="sk" hreflang="sk" data-title="Hydrolýza" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Hidroliza" title="Hidroliza – Slovenian" lang="sl" hreflang="sl" data-title="Hidroliza" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%A6%D8%A7%D9%88%DB%8E%D9%86" title="ئاوێن – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ئاوێن" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A5%D0%B8%D0%B4%D1%80%D0%BE%D0%BB%D0%B8%D0%B7%D0%B0" title="Хидролиза – Serbian" lang="sr" hreflang="sr" data-title="Хидролиза" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Hidroliza" title="Hidroliza – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Hidroliza" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Hidrolisis" title="Hidrolisis – Sundanese" lang="su" hreflang="su" data-title="Hidrolisis" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Hydrolyysi" title="Hydrolyysi – Finnish" lang="fi" hreflang="fi" data-title="Hydrolyysi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Hydrolys" title="Hydrolys – Swedish" lang="sv" hreflang="sv" data-title="Hydrolys" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%A8%E0%AF%80%E0%AE%B0%E0%AE%BE%E0%AE%B1%E0%AF%8D%E0%AE%AA%E0%AE%95%E0%AF%81%E0%AE%A4%E0%AF%8D%E0%AE%A4%E0%AE%B2%E0%AF%8D" title="நீராற்பகுத்தல் – Tamil" lang="ta" hreflang="ta" data-title="நீராற்பகுத்தல்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/%D0%93%D0%B8%D0%B4%D1%80%D0%BE%D0%BB%D0%B8%D0%B7" title="Гидролиз – Tatar" lang="tt" hreflang="tt" data-title="Гидролиз" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%9C%E0%B0%B2%E0%B0%B5%E0%B0%BF%E0%B0%B6%E0%B1%8D%E0%B0%B2%E0%B1%87%E0%B0%B7%E0%B0%A3" title="జలవిశ్లేషణ – Telugu" lang="te" hreflang="te" data-title="జలవిశ్లేషణ" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Hidroliz" title="Hidroliz – Turkish" lang="tr" hreflang="tr" data-title="Hidroliz" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%93%D1%96%D0%B4%D1%80%D0%BE%D0%BB%D1%96%D0%B7" title="Гідроліз – Ukrainian" lang="uk" hreflang="uk" data-title="Гідроліз" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%A2%D8%A8_%D9%BE%D8%A7%D8%B4%DB%8C%D8%AF%DA%AF%DB%8C" title="آب پاشیدگی – Urdu" lang="ur" hreflang="ur" data-title="آب پاشیدگی" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Th%E1%BB%A7y_ph%C3%A2n" title="Thủy phân – Vietnamese" lang="vi" hreflang="vi" data-title="Thủy phân" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E6%B0%B4%E8%A7%A3" title="水解 – Wu" lang="wuu" hreflang="wuu" data-title="水解" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E6%B0%B4%E8%A7%A3" title="水解 – Cantonese" lang="yue" hreflang="yue" data-title="水解" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E6%B0%B4%E8%A7%A3" title="水解 – Chinese" lang="zh" hreflang="zh" data-title="水解" data-language-autonym="中文" data-language-local-name="Chinese" 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class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"><span class="mw-redirectedfrom">(Redirected from <a href="/w/index.php?title=Hydrolyzed&redirect=no" class="mw-redirect" title="Hydrolyzed">Hydrolyzed</a>)</span></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Cleavage of chemical bonds by the addition of water</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Hydrogenolysis" title="Hydrogenolysis">Hydrogenolysis</a>, <a href="/wiki/Hydroxylation" title="Hydroxylation">Hydroxylation</a>, or <a href="/wiki/Water_splitting" title="Water splitting">Water splitting</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-More_citations_needed plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article <b>needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a></b>.<span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Hydrolysis" title="Special:EditPage/Hydrolysis">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a>. Unsourced material may be challenged and removed.<br /><small><span class="plainlinks"><i>Find sources:</i> <a rel="nofollow" class="external text" href="https://www.google.com/search?as_eq=wikipedia&q=%22Hydrolysis%22">"Hydrolysis"</a> – <a rel="nofollow" class="external text" href="https://www.google.com/search?tbm=nws&q=%22Hydrolysis%22+-wikipedia&tbs=ar:1">news</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?&q=%22Hydrolysis%22&tbs=bkt:s&tbm=bks">newspapers</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?tbs=bks:1&q=%22Hydrolysis%22+-wikipedia">books</a> <b>·</b> <a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?q=%22Hydrolysis%22">scholar</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.jstor.org/action/doBasicSearch?Query=%22Hydrolysis%22&acc=on&wc=on">JSTOR</a></span></small></span> <span class="date-container"><i>(<span class="date">January 2021</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Hydrolysis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Hydrolysis.png/370px-Hydrolysis.png" decoding="async" width="370" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Hydrolysis.png/555px-Hydrolysis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Hydrolysis.png/740px-Hydrolysis.png 2x" data-file-width="984" data-file-height="168" /></a><figcaption>Generic hydrolysis reaction. (The 2-way yield symbol indicates a <a href="/wiki/Chemical_equilibrium" title="Chemical equilibrium">chemical equilibrium</a> in which hydrolysis and <a href="/wiki/Condensation_reaction" title="Condensation reaction">condensation</a> are reversible.)</figcaption></figure> <p><b>Hydrolysis</b> (<span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="'h' in 'hi'">h</span><span title="/aɪ/: 'i' in 'tide'">aɪ</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'d' in 'dye'">d</span><span title="'r' in 'rye'">r</span><span title="/ɒ/: 'o' in 'body'">ɒ</span><span title="'l' in 'lie'">l</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'s' in 'sigh'">s</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'s' in 'sigh'">s</span></span>/</a></span></span>; from <a href="/wiki/Ancient_Greek_language" class="mw-redirect" title="Ancient Greek language">Ancient Greek</a> <i> hydro-</i> 'water' and <i> lysis</i> 'to unbind') is any chemical reaction in which a molecule of <a href="/wiki/Water" title="Water">water</a> breaks one or more chemical bonds. The term is used broadly for <a href="/wiki/Substitution_reaction" title="Substitution reaction">substitution</a>, <a href="/wiki/Elimination_reaction" title="Elimination reaction">elimination</a>, and <a href="/wiki/Solvation" title="Solvation">solvation</a> reactions in which water is the <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a>.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Biological hydrolysis is the cleavage of <a href="/wiki/Biomolecule" title="Biomolecule">biomolecules</a> where a water molecule is consumed to effect the separation of a larger molecule into component parts. When a <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrate</a> is broken into its component sugar molecules by hydrolysis (e.g., <a href="/wiki/Sucrose" title="Sucrose">sucrose</a> being broken down into <a href="/wiki/Glucose" title="Glucose">glucose</a> and <a href="/wiki/Fructose" title="Fructose">fructose</a>), this is recognized as <a href="/wiki/Saccharification" title="Saccharification">saccharification</a>.<sup id="cite_ref-saccharification_2-0" class="reference"><a href="#cite_note-saccharification-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Hydrolysis reactions can be the reverse of a <a href="/wiki/Condensation_reaction" title="Condensation reaction">condensation reaction</a> in which two molecules join into a larger one and eject a water molecule. Thus hydrolysis adds water to break down, whereas condensation builds up by removing water.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Types">Types</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrolysis&action=edit&section=1" title="Edit section: Types"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Usually hydrolysis is a chemical process in which a molecule of water is added to a substance. Sometimes this addition causes both the substance and water molecule to split into two parts. In such reactions, one fragment of the target molecule (or parent molecule) gains a <a href="/wiki/Hydrogen_ion" title="Hydrogen ion">hydrogen ion</a>. It breaks a chemical bond in the compound. </p> <div class="mw-heading mw-heading3"><h3 id="Salts">Salts</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrolysis&action=edit&section=2" title="Edit section: Salts"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A common kind of hydrolysis occurs when a <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a> of a <a href="/wiki/Weak_acid" class="mw-redirect" title="Weak acid">weak acid</a> or <a href="/wiki/Weak_base" title="Weak base">weak base</a> (or both) is dissolved in water. <a href="/wiki/Self-ionization_of_water" title="Self-ionization of water">Water spontaneously ionizes</a> into <a href="/wiki/Hydroxide" title="Hydroxide">hydroxide anions</a> and <a href="/wiki/Hydronium" title="Hydronium">hydronium cations</a>. The salt also dissociates into its constituent anions and cations. For example, <a href="/wiki/Sodium_acetate" title="Sodium acetate">sodium acetate</a> dissociates in water into <a href="/wiki/Sodium" title="Sodium">sodium</a> and <a href="/wiki/Acetate" title="Acetate">acetate</a> ions. Sodium ions react very little with the hydroxide ions whereas the acetate ions combine with hydronium ions to produce <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>. In this case the net result is a relative excess of hydroxide ions, yielding a basic <a href="/wiki/Solution_(chemistry)" title="Solution (chemistry)">solution</a>. </p><p><a href="/wiki/Strong_acids" class="mw-redirect" title="Strong acids">Strong acids</a> also undergo hydrolysis. For example, dissolving <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> (<style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>SO<sub class="template-chem2-sub">4</sub></span>) in water is accompanied by hydrolysis to give <a href="/wiki/Hydronium" title="Hydronium">hydronium</a> and <a href="/wiki/Bisulfate" class="mw-redirect" title="Bisulfate">bisulfate</a>, the sulfuric acid's <a href="/wiki/Conjugate_acid" class="mw-redirect" title="Conjugate acid">conjugate base</a>. For a more technical discussion of what occurs during such a hydrolysis, see <a href="/wiki/Br%C3%B8nsted%E2%80%93Lowry_acid%E2%80%93base_theory" title="Brønsted–Lowry acid–base theory">Brønsted–Lowry acid–base theory</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Esters_and_amides">Esters and amides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrolysis&action=edit&section=3" title="Edit section: Esters and amides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Ester_hydrolysis" title="Ester hydrolysis">Ester hydrolysis</a></div> <p>Acid–base-catalysed hydrolyses are very common; one example is the hydrolysis of <a href="/wiki/Amide" title="Amide">amides</a> or <a href="/wiki/Ester" title="Ester">esters</a>. Their hydrolysis occurs when the <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a> (a nucleus-seeking agent, e.g., water or hydroxyl ion) attacks the carbon of the <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl group</a> of the <a href="/wiki/Ester" title="Ester">ester</a> or <a href="/wiki/Amide" title="Amide">amide</a>. In an aqueous base, hydroxyl ions are better nucleophiles than polar molecules such as water. In acids, the carbonyl group becomes protonated, and this leads to a much easier nucleophilic attack. The products for both hydrolyses are compounds with <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> groups. </p><p>Perhaps the oldest commercially practiced example of ester hydrolysis is <a href="/wiki/Saponification" title="Saponification">saponification</a> (formation of soap). It is the hydrolysis of a <a href="/wiki/Triglyceride" title="Triglyceride">triglyceride</a> (fat) with an aqueous base such as <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> (NaOH). During the process, <a href="/wiki/Glycerol" title="Glycerol">glycerol</a> is formed, and the <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a> react with the base, converting them to salts. These salts are called soaps, commonly used in households. </p><p>In addition, in living systems, most biochemical reactions (including ATP hydrolysis) take place during the catalysis of <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>. The catalytic action of enzymes allows the hydrolysis of <a href="/wiki/Protein" title="Protein">proteins</a>, fats, oils, and <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a>. As an example, one may consider <a href="/wiki/Protease" title="Protease">proteases</a> (enzymes that aid <a href="/wiki/Digestion" title="Digestion">digestion</a> by causing hydrolysis of <a href="/wiki/Peptide_bond" title="Peptide bond">peptide bonds</a> in <a href="/wiki/Protein" title="Protein">proteins</a>). They catalyze the hydrolysis of interior peptide bonds in peptide chains, as opposed to <a href="/wiki/Exopeptidase" title="Exopeptidase">exopeptidases</a> (another class of enzymes, that catalyze the hydrolysis of terminal peptide bonds, liberating one free amino acid at a time). </p><p>However, proteases do not catalyze the hydrolysis of all kinds of proteins. Their action is stereo-selective: Only proteins with a certain tertiary structure are targeted as some kind of orienting force is needed to place the amide group in the proper position for catalysis. The necessary contacts between an enzyme and its substrates (proteins) are created because the enzyme folds in such a way as to form a crevice into which the substrate fits; the crevice also contains the catalytic groups. Therefore, proteins that do not fit into the crevice will not undergo hydrolysis. This specificity preserves the integrity of other proteins such as <a href="/wiki/Hormone" title="Hormone">hormones</a>, and therefore the biological system continues to function normally. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Acid-CatAmideHydrolMarch.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Acid-CatAmideHydrolMarch.png/370px-Acid-CatAmideHydrolMarch.png" decoding="async" width="370" height="238" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Acid-CatAmideHydrolMarch.png/555px-Acid-CatAmideHydrolMarch.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Acid-CatAmideHydrolMarch.png/740px-Acid-CatAmideHydrolMarch.png 2x" data-file-width="1430" data-file-height="920" /></a><figcaption>Mechanism for acid-catalyzed hydrolysis of an amide.</figcaption></figure> <p>Upon hydrolysis, an <a href="/wiki/Amide" title="Amide">amide</a> converts into a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> and an <a href="/wiki/Amine" title="Amine">amine</a> or <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> (which in the presence of acid are immediately converted to ammonium salts). One of the two oxygen groups on the carboxylic acid are derived from a water molecule and the amine (or ammonia) gains the hydrogen ion. The hydrolysis of <a href="/wiki/Peptide_bond" title="Peptide bond">peptides</a> gives <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a>. </p><p>Many <a href="/wiki/Polyamide" title="Polyamide">polyamide</a> polymers such as <a href="/wiki/Nylon_6,6" class="mw-redirect" title="Nylon 6,6">nylon 6,6</a> hydrolyze in the presence of strong acids. The process leads to <a href="/wiki/Depolymerization" title="Depolymerization">depolymerization</a>. For this reason nylon products fail by fracturing when exposed to small amounts of acidic water. Polyesters are also susceptible to similar <a href="/wiki/Polymer_degradation" title="Polymer degradation">polymer degradation</a> reactions. The problem is known as <a href="/wiki/Environmental_stress_cracking" title="Environmental stress cracking">environmental stress cracking</a>. </p> <div class="mw-heading mw-heading3"><h3 id="ATP">ATP</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrolysis&action=edit&section=4" title="Edit section: ATP"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydrolysis is related to <a href="/wiki/Energy_metabolism" class="mw-redirect" title="Energy metabolism">energy metabolism</a> and storage. All living cells require a continual supply of energy for two main purposes: the <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a> of micro and macromolecules, and the active transport of ions and molecules across cell membranes. The energy derived from the <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> of nutrients is not used directly but, by means of a complex and long sequence of reactions, it is channeled into a special energy-storage molecule, <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">adenosine triphosphate</a> (ATP). The ATP molecule contains <a href="/wiki/Pyrophosphate" title="Pyrophosphate">pyrophosphate</a> linkages (bonds formed when two phosphate units are combined) that release energy when needed. ATP can undergo hydrolysis in two ways: Firstly, the removal of terminal phosphate to form <a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">adenosine diphosphate</a> (ADP) and inorganic phosphate, with the reaction: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {ATP + H2O -> ADP + P_{i}}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>ATP</mtext> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> <mo stretchy="false">⟶</mo> <mtext>ADP</mtext> <mo>+</mo> <msubsup> <mtext>P</mtext> <mrow class="MJX-TeXAtom-ORD"> <mtext>i</mtext> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {ATP + H2O -> ADP + P_{i}}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/74d01c19458519bcf6df7afe397902b490bf2bae" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:27.76ex; height:2.843ex;" alt="{\displaystyle {\ce {ATP + H2O -> ADP + P_{i}}}}"></span></dd></dl> <p>Secondly, the removal of a terminal diphosphate to yield <a href="/wiki/Adenosine_monophosphate" title="Adenosine monophosphate">adenosine monophosphate</a> (AMP) and <a href="/wiki/Pyrophosphate" title="Pyrophosphate">pyrophosphate</a>. The latter usually undergoes further cleavage into its two constituent phosphates. This results in biosynthesis reactions, which usually occur in chains, that can be driven in the direction of synthesis when the phosphate bonds have undergone hydrolysis. </p> <div class="mw-heading mw-heading3"><h3 id="Polysaccharides">Polysaccharides<span class="anchor" id="saccharification"></span></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrolysis&action=edit&section=5" title="Edit section: Polysaccharides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Sucrose-inkscape.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Sucrose-inkscape.svg/220px-Sucrose-inkscape.svg.png" decoding="async" width="220" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Sucrose-inkscape.svg/330px-Sucrose-inkscape.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Sucrose-inkscape.svg/440px-Sucrose-inkscape.svg.png 2x" data-file-width="434" data-file-height="205" /></a><figcaption>Sucrose. The glycoside bond is represented by the central oxygen atom, which holds the two monosaccharide units together.</figcaption></figure> <p><a href="/wiki/Monosaccharide" title="Monosaccharide">Monosaccharides</a> can be linked together by <a href="/wiki/Glycosidic_bond" title="Glycosidic bond">glycosidic bonds</a>, which can be cleaved by hydrolysis. Two, three, several or many monosaccharides thus linked form <a href="/wiki/Disaccharide" title="Disaccharide">disaccharides</a>, <a href="/wiki/Trisaccharide" title="Trisaccharide">trisaccharides</a>, <a href="/wiki/Oligosaccharide" title="Oligosaccharide">oligosaccharides</a>, or <a href="/wiki/Polysaccharide" title="Polysaccharide">polysaccharides</a>, respectively. Enzymes that hydrolyze glycosidic bonds are called "<a href="/wiki/Glycoside_hydrolase" title="Glycoside hydrolase">glycoside hydrolases</a>" or "glycosidases". </p><p>The best-known disaccharide is <a href="/wiki/Sucrose" title="Sucrose">sucrose</a> (table sugar). Hydrolysis of sucrose yields <a href="/wiki/Glucose" title="Glucose">glucose</a> and <a href="/wiki/Fructose" title="Fructose">fructose</a>. <a href="/wiki/Invertase" title="Invertase">Invertase</a> is a <a href="/wiki/Sucrase" title="Sucrase">sucrase</a> used industrially for the hydrolysis of sucrose to so-called <a href="/wiki/Invert_sugar" class="mw-redirect" title="Invert sugar">invert sugar</a>. <a href="/wiki/Lactase" title="Lactase">Lactase</a> is essential for digestive hydrolysis of <a href="/wiki/Lactose" title="Lactose">lactose</a> in milk; many adult humans do not produce lactase and <a href="/wiki/Lactose_intolerance" title="Lactose intolerance">cannot digest the lactose</a> in milk. </p><p>The hydrolysis of polysaccharides to soluble sugars can be recognized as <a href="/wiki/Saccharification" title="Saccharification">saccharification</a>.<sup id="cite_ref-saccharification_2-1" class="reference"><a href="#cite_note-saccharification-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Malt made from <a href="/wiki/Barley" title="Barley">barley</a> is used as a source of β-amylase to break down <a href="/wiki/Starch" title="Starch">starch</a> into the disaccharide <a href="/wiki/Maltose" title="Maltose">maltose</a>, which can be used by yeast to <a href="/wiki/Brewing" title="Brewing">produce beer</a>. Other <a href="/wiki/Amylase" title="Amylase">amylase</a> enzymes may convert starch to glucose or to oligosaccharides. <a href="/wiki/Cellulose" title="Cellulose">Cellulose</a> is first hydrolyzed to <a href="/wiki/Cellobiose" title="Cellobiose">cellobiose</a> by <a href="/wiki/Cellulase" title="Cellulase">cellulase</a> and then cellobiose is further hydrolyzed to <a href="/wiki/Glucose" title="Glucose">glucose</a> by <a href="/wiki/Beta-glucosidase" class="mw-redirect" title="Beta-glucosidase">beta-glucosidase</a>. <a href="/wiki/Ruminants" class="mw-redirect" title="Ruminants">Ruminants</a> such as cows are able to hydrolyze cellulose into cellobiose and then glucose because of <a href="/wiki/Symbiosis" title="Symbiosis">symbiotic</a> bacteria that produce cellulases. </p> <div class="mw-heading mw-heading3"><h3 id="DNA">DNA</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrolysis&action=edit&section=6" title="Edit section: DNA"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydrolysis of <a href="/wiki/DNA" title="DNA">DNA</a> occurs at a significant rate in vivo.<sup id="cite_ref-Lindahl1993_4-0" class="reference"><a href="#cite_note-Lindahl1993-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> For example, it is estimated that in each human cell 2,000 to 10,000 DNA <a href="/wiki/Purine" title="Purine">purine</a> bases turn over every day due to hydrolytic depurination, and that this is largely counteracted by specific rapid <a href="/wiki/DNA_repair" title="DNA repair">DNA repair</a> processes.<sup id="cite_ref-Lindahl1993_4-1" class="reference"><a href="#cite_note-Lindahl1993-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Hydrolytic DNA damages that fail to be accurately repaired may contribute to <a href="/wiki/Carcinogenesis" title="Carcinogenesis">carcinogenesis</a> and <a href="/wiki/Ageing" title="Ageing">ageing</a>.<sup id="cite_ref-Lindahl1993_4-2" class="reference"><a href="#cite_note-Lindahl1993-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Metal_aqua_ions">Metal aqua ions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrolysis&action=edit&section=7" title="Edit section: Metal aqua ions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Metal_ions_in_aqueous_solution" title="Metal ions in aqueous solution">Metal ions in aqueous solution</a></div> <p>Metal ions are <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acids</a>, and in <a href="/wiki/Aqueous_solution" title="Aqueous solution">aqueous solution</a> they form <a href="/wiki/Metal_aquo_complex" title="Metal aquo complex">metal aquo complexes</a> of the general formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">M(H<sub class="template-chem2-sub">2</sub>O)<sub class="template-chem2-sub"><i>n</i></sub><sup class="template-chem2-sup"><i>m</i>+</sup></span>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> The aqua ions undergo hydrolysis, to a greater or lesser extent. The first hydrolysis step is given generically as </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {M(H2O)_{\mathit {n}}^{{\mathit {m}}+}{}+H2O<=>M(H2O)_{{\mathit {n}}-1}(OH)^{({\mathit {m}}-1){}+}{}+H3O+}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>M</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mtext class="MJX-tex-mathit" mathvariant="italic">n</mtext> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mtext class="MJX-tex-mathit" mathvariant="italic">m</mtext> </mrow> </mrow> <mo>+</mo> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> </mrow> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> <mrow class="MJX-TeXAtom-REL"> <mover> <mrow class="MJX-TeXAtom-OP MJX-fixedlimits"> <mrow class="MJX-TeXAtom-ORD"> <mpadded height="0" depth="0"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">↽</mo> </mrow> <mspace width="negativethinmathspace" /> <mspace width="negativethinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </mpadded> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="false" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mspace width="negativethinmathspace" /> <mspace width="negativethinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">⇀</mo> </mrow> </mrow> </mstyle> </mrow> </mover> </mrow> <mtext>M</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mtext class="MJX-tex-mathit" mathvariant="italic">n</mtext> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mn>1</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>OH</mtext> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mtext class="MJX-tex-mathit" mathvariant="italic">m</mtext> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mn>1</mn> <mspace width="thinmathspace" /> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> </mrow> <mo>+</mo> </mrow> </msup> <mrow class="MJX-TeXAtom-ORD"> </mrow> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msup> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {M(H2O)_{\mathit {n}}^{{\mathit {m}}+}{}+H2O<=>M(H2O)_{{\mathit {n}}-1}(OH)^{({\mathit {m}}-1){}+}{}+H3O+}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/cc3715e54504136341847fc41bddb1a4e7e81f68" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.171ex; width:56.236ex; height:3.843ex;" alt="{\displaystyle {\ce {M(H2O)_{\mathit {n}}^{{\mathit {m}}+}{}+H2O<=>M(H2O)_{{\mathit {n}}-1}(OH)^{({\mathit {m}}-1){}+}{}+H3O+}}}"></span></dd></dl> <p>Thus the aqua <a href="/wiki/Cation" class="mw-redirect" title="Cation">cations</a> behave as acids in terms of <a href="/wiki/Br%C3%B8nsted%E2%80%93Lowry_acid%E2%80%93base_theory" title="Brønsted–Lowry acid–base theory">Brønsted–Lowry acid–base theory</a>. This effect is easily explained by considering the <a href="/wiki/Inductive_effect" title="Inductive effect">inductive effect</a> of the positively charged metal ion, which weakens the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O−H</span> bond of an attached water molecule, making the liberation of a proton relatively easy. </p><p>The <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">dissociation constant</a>, pK<sub>a</sub>, for this reaction is more or less linearly related to the charge-to-size ratio of the metal ion.<sup id="cite_ref-bm_7-0" class="reference"><a href="#cite_note-bm-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Ions with low charges, such as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Na<sup class="template-chem2-sup">+</sup></span> are very weak acids with almost imperceptible hydrolysis. Large divalent ions such as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ca<sup>2+</sup></span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Zn<sup>2+</sup></span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sn<sup>2+</sup></span> and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Pb<sup>2+</sup></span> have a pK<sub>a</sub> of 6 or more and would not normally be classed as acids, but small divalent ions such as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Be<sup>2+</sup></span> undergo extensive hydrolysis. Trivalent ions like <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Al<sup>3+</sup></span> and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Fe<sup>3+</sup></span> are weak acids whose pK<sub>a</sub> is comparable to that of <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>. Solutions of salts such as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">BeCl<sub class="template-chem2-sub">2</sub></span> or <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Al(NO<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span> in water are noticeably <a href="/wiki/Acidic" class="mw-redirect" title="Acidic">acidic</a>; the hydrolysis can be <a href="/wiki/Le_chatelier%27s_principle" class="mw-redirect" title="Le chatelier's principle">suppressed</a> by adding an acid such as <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a>, making the solution more acidic. </p><p>Hydrolysis may proceed beyond the first step, often with the formation of polynuclear species via the process of <a href="/wiki/Olation" title="Olation">olation</a>.<sup id="cite_ref-bm_7-1" class="reference"><a href="#cite_note-bm-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Some "exotic" species such as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sn<sub class="template-chem2-sub">3</sub>(OH)<span class="template-chem2-su"><span>2+</span><span>4</span></span></span><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> are well characterized. Hydrolysis tends to proceed as <a href="/wiki/PH" title="PH">pH</a> rises leading, in many cases, to the precipitation of a hydroxide such as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Al(OH)<sub class="template-chem2-sub">3</sub></span> or <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">AlO(OH)</span>. These substances, major constituents of <a href="/wiki/Bauxite" title="Bauxite">bauxite</a>, are known as <a href="/wiki/Laterite" title="Laterite">laterites</a> and are formed by leaching from rocks of most of the ions other than aluminium and iron and subsequent hydrolysis of the remaining aluminium and iron. </p> <div class="mw-heading mw-heading3"><h3 id="Mechanism_strategies">Mechanism strategies</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrolysis&action=edit&section=8" title="Edit section: Mechanism strategies"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Acetal" title="Acetal">Acetals</a>, <a href="/wiki/Imine" title="Imine">imines</a>, and <a href="/wiki/Enamine" title="Enamine">enamines</a> can be converted back into <a href="/wiki/Ketone" title="Ketone">ketones</a> by treatment with excess water under acid-catalyzed conditions: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RO·OR−H<sub class="template-chem2-sub">3</sub>O−O</span>; <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NR·H<sub class="template-chem2-sub">3</sub>O−O</span>; <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RNR−H<sub class="template-chem2-sub">3</sub>O−O</span>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Catalysis">Catalysis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrolysis&action=edit&section=9" title="Edit section: Catalysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Acidic_hydrolysis">Acidic hydrolysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrolysis&action=edit&section=10" title="Edit section: Acidic hydrolysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Acid_catalysis" title="Acid catalysis">Acid catalysis</a> can be applied to hydrolyses.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> For example, in the conversion of <a href="/wiki/Cellulose" title="Cellulose">cellulose</a> or <a href="/wiki/Starch" title="Starch">starch</a> to <a href="/wiki/Glucose" title="Glucose">glucose</a>.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Carboxylic acids can be produced from acid hydrolysis of esters.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Acids catalyze hydrolysis of <a href="/wiki/Nitriles" class="mw-redirect" title="Nitriles">nitriles</a> to amides. Acid hydrolysis <i>does not</i> usually refer to the acid catalyzed addition of the elements of water to double or triple bonds by <a href="/wiki/Electrophilic_addition" title="Electrophilic addition">electrophilic addition</a> as may originate from a <a href="/wiki/Hydration_reaction" title="Hydration reaction">hydration reaction</a>. Acid hydrolysis is used to prepare monosaccharide with the help of <a href="/wiki/Mineral_acid" title="Mineral acid">mineral acids</a> but formic acid and <a href="/wiki/Trifluoroacetic_acid" title="Trifluoroacetic acid">trifluoroacetic acid</a> have been used.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>Acid hydrolysis can be utilized in the pretreatment of cellulosic material, so as to cut the interchain linkages in hemicellulose and cellulose.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Alkaline_hydrolysis">Alkaline hydrolysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrolysis&action=edit&section=11" title="Edit section: Alkaline hydrolysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alkaline hydrolysis usually refers to types of <a href="/wiki/Nucleophilic_substitution" title="Nucleophilic substitution">nucleophilic substitution</a> reactions in which the attacking <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a> is a <a href="/wiki/Hydroxide_ion" class="mw-redirect" title="Hydroxide ion">hydroxide ion</a>. The best known type is <a href="/wiki/Saponification" title="Saponification">saponification</a>: cleaving <a href="/wiki/Ester" title="Ester">esters</a> into <a href="/wiki/Carboxylate" title="Carboxylate">carboxylate</a> salts and <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a>. In <a href="/wiki/Ester_hydrolysis" title="Ester hydrolysis">ester hydrolysis</a>, the hydroxide ion nucleophile attacks the <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> carbon. This mechanism is supported by <a href="/wiki/Isotope_labeling" class="mw-redirect" title="Isotope labeling">isotope labeling</a> experiments. For example, when <a href="/wiki/Ethyl_propionate" title="Ethyl propionate">ethyl propionate</a> with an <a href="/wiki/Oxygen-18" title="Oxygen-18">oxygen-18</a> labeled ethoxy group is treated with <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> (NaOH), the oxygen-18 is completely absent from the <a href="/wiki/Sodium_propionate" title="Sodium propionate">sodium propionate</a> product and is found exclusively in the <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> formed.<sup id="cite_ref-mcmurry_17-0" class="reference"><a href="#cite_note-mcmurry-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p><span typeof="mw:File"><a href="/wiki/File:Nucleophilic_Acyl_Substitution_with_a_Labeled_Oxygen.png" class="mw-file-description" title="Reacting isotopically labeled ethyl propionate with sodium hydroxide proves the proposed mechanism for nucleophilic acyl substitution."><img alt="Reacting isotopically labeled ethyl propionate with sodium hydroxide proves the proposed mechanism for nucleophilic acyl substitution." src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1d/Nucleophilic_Acyl_Substitution_with_a_Labeled_Oxygen.png/563px-Nucleophilic_Acyl_Substitution_with_a_Labeled_Oxygen.png" decoding="async" width="563" height="67" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1d/Nucleophilic_Acyl_Substitution_with_a_Labeled_Oxygen.png/845px-Nucleophilic_Acyl_Substitution_with_a_Labeled_Oxygen.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1d/Nucleophilic_Acyl_Substitution_with_a_Labeled_Oxygen.png/1126px-Nucleophilic_Acyl_Substitution_with_a_Labeled_Oxygen.png 2x" data-file-width="1974" data-file-height="234" /></a></span> </p><p>The reaction is often used to solubilize solid organic matter. <a href="/wiki/Chemical_drain_cleaner" class="mw-redirect" title="Chemical drain cleaner">Chemical drain cleaners</a> take advantage of this method to dissolve hair and fat in pipes. The reaction is also used to <a href="/wiki/Alkaline_hydrolysis_(body_disposal)" class="mw-redirect" title="Alkaline hydrolysis (body disposal)">dispose of human and other animal remains</a> as an alternative to traditional burial or cremation. </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrolysis&action=edit&section=12" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col div-col-small"> <ul><li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">Adenosine triphosphate</a></li> <li><a href="/wiki/Water_cremation" title="Water cremation">Water cremation</a></li> <li><a href="/wiki/Catabolism" title="Catabolism">Catabolism</a></li> <li><a href="/wiki/Condensation_reaction" title="Condensation reaction">Condensation reaction</a></li> <li><a href="/wiki/Dehydration_reaction" title="Dehydration reaction">Dehydration reaction</a></li> <li><a href="/wiki/Hydrolysis_constant" title="Hydrolysis constant">Hydrolysis constant</a></li> <li><a href="/wiki/Inhibitor_protein" title="Inhibitor protein">Inhibitor protein</a></li> <li><a href="/wiki/Polymer_degradation" title="Polymer degradation">Polymer degradation</a></li> <li><a href="/wiki/Proteolysis" title="Proteolysis">Proteolysis</a></li> <li><a href="/wiki/Saponification" title="Saponification">Saponification</a></li> <li><a href="/wiki/Sol%E2%80%93gel_process#Polymerization" title="Sol–gel process">Sol–gel polymerisation</a></li> <li><a href="/wiki/Solvolysis" title="Solvolysis">Solvolysis</a></li> <li><a href="/wiki/Thermal_hydrolysis" title="Thermal hydrolysis">Thermal hydrolysis</a></li></ul> </div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrolysis&action=edit&section=13" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/H02902.html">Hydrolysis</a>". <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.H02902">10.1351/goldbook.H02902</a><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/S05762.html">Solvolysis</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.S05762">10.1351/goldbook.S05762</a></span> </li> <li id="cite_note-saccharification-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-saccharification_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-saccharification_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.merriam-webster.com/dictionary/saccharification">"Definition of Saccharification"</a>. <i>Merriam-Webster</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210107190250/https://www.merriam-webster.com/dictionary/saccharification">Archived</a> from the original on 7 January 2021<span class="reference-accessdate">. Retrieved <span class="nowrap">8 September</span> 2020</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Merriam-Webster&rft.atitle=Definition+of+Saccharification&rft_id=https%3A%2F%2Fwww.merriam-webster.com%2Fdictionary%2Fsaccharification&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrolysis" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSteane" class="citation web cs1">Steane, Richard. <a rel="nofollow" class="external text" href="https://www.biotopics.co.uk/as/condensation_and_hydrolysis.html">"Condensation and Hydrolysis"</a>. <i>www.biotopics.co.uk</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20201127013953/https://biotopics.co.uk/as/condensation_and_hydrolysis.html">Archived</a> from the original on 2020-11-27<span class="reference-accessdate">. Retrieved <span class="nowrap">2020-11-13</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.biotopics.co.uk&rft.atitle=Condensation+and+Hydrolysis&rft.aulast=Steane&rft.aufirst=Richard&rft_id=https%3A%2F%2Fwww.biotopics.co.uk%2Fas%2Fcondensation_and_hydrolysis.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrolysis" class="Z3988"></span></span> </li> <li id="cite_note-Lindahl1993-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Lindahl1993_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Lindahl1993_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Lindahl1993_4-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text">Lindahl T. Instability and decay of the primary structure of DNA. Nature. 1993 Apr 22;362(6422):709-15. doi: 10.1038/362709a0. PMID 8469282</span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBurgess1978" class="citation book cs1">Burgess, John (1978). <i>Metal Ions in Solution</i>. Chichester: Ellis Horwood. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0853120278" title="Special:BookSources/978-0853120278"><bdi>978-0853120278</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Metal+Ions+in+Solution&rft.place=Chichester&rft.pub=Ellis+Horwood&rft.date=1978&rft.isbn=978-0853120278&rft.aulast=Burgess&rft.aufirst=John&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrolysis" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRichens1997" class="citation book cs1">Richens, D. T. (1997). <i>The Chemistry of Aqua Ions: Synthesis, Structure, and Reactivity: A Tour through the Periodic Table of the Elements</i>. Wiley. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-471-97058-1" title="Special:BookSources/0-471-97058-1"><bdi>0-471-97058-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Chemistry+of+Aqua+Ions%3A+Synthesis%2C+Structure%2C+and+Reactivity%3A+A+Tour+through+the+Periodic+Table+of+the+Elements&rft.pub=Wiley&rft.date=1997&rft.isbn=0-471-97058-1&rft.aulast=Richens&rft.aufirst=D.+T.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrolysis" class="Z3988"></span></span> </li> <li id="cite_note-bm-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-bm_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-bm_7-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBaesMesmer1976" class="citation book cs1">Baes, Charles F.; Mesmer, Robert E. (1976). <i>The Hydrolysis of Cations</i>. New York: Wiley. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780471039853" title="Special:BookSources/9780471039853"><bdi>9780471039853</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Hydrolysis+of+Cations&rft.place=New+York&rft.pub=Wiley&rft.date=1976&rft.isbn=9780471039853&rft.aulast=Baes&rft.aufirst=Charles+F.&rft.au=Mesmer%2C+Robert+E.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrolysis" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGreenwoodEarnshaw1997" class="citation book cs1"><a href="/wiki/Norman_Greenwood" title="Norman Greenwood">Greenwood, Norman N.</a>; Earnshaw, Alan (1997). <i>Chemistry of the Elements</i> (2nd ed.). <a href="/wiki/Butterworth-Heinemann" title="Butterworth-Heinemann">Butterworth-Heinemann</a>. p. 384. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-037941-8" title="Special:BookSources/978-0-08-037941-8"><bdi>978-0-08-037941-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Chemistry+of+the+Elements&rft.pages=384&rft.edition=2nd&rft.pub=Butterworth-Heinemann&rft.date=1997&rft.isbn=978-0-08-037941-8&rft.aulast=Greenwood&rft.aufirst=Norman+N.&rft.au=Earnshaw%2C+Alan&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrolysis" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKlein2012" class="citation book cs1">Klein, David (2012). <i>Organic Chemistry</i>. Wiley. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-75614-9" title="Special:BookSources/978-0-471-75614-9"><bdi>978-0-471-75614-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+Chemistry&rft.pub=Wiley&rft.date=2012&rft.isbn=978-0-471-75614-9&rft.aulast=Klein&rft.aufirst=David&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrolysis" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSpeight2016" class="citation book cs1">Speight, James G. (2 November 2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=NSRBCgAAQBAJ&pg=PA143"><i>Hydrolysis</i></a>. pp. 143–144. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780128006689" title="Special:BookSources/9780128006689"><bdi>9780128006689</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Hydrolysis&rft.pages=143-144&rft.date=2016-11-02&rft.isbn=9780128006689&rft.aulast=Speight&rft.aufirst=James+G.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DNSRBCgAAQBAJ%26pg%3DPA143&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrolysis" class="Z3988"></span> in <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSpeight2017" class="citation book cs1">Speight, James G. (2017). "Industrial Organic Chemistry". <i>Environmental Organic Chemistry for Engineers</i>. pp. 87–151. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FB978-0-12-804492-6.00003-4">10.1016/B978-0-12-804492-6.00003-4</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-804492-6" title="Special:BookSources/978-0-12-804492-6"><bdi>978-0-12-804492-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Industrial+Organic+Chemistry&rft.btitle=Environmental+Organic+Chemistry+for+Engineers&rft.pages=87-151&rft.date=2017&rft_id=info%3Adoi%2F10.1016%2FB978-0-12-804492-6.00003-4&rft.isbn=978-0-12-804492-6&rft.aulast=Speight&rft.aufirst=James+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrolysis" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGoldstein1983" class="citation book cs1">Goldstein, Irving S. (1983). "Hydrolysis of Cellulose by Acids". <i>Biomass Utilization</i>. pp. 559–566. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-1-4757-0833-2_30">10.1007/978-1-4757-0833-2_30</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4757-0835-6" title="Special:BookSources/978-1-4757-0835-6"><bdi>978-1-4757-0835-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Hydrolysis+of+Cellulose+by+Acids&rft.btitle=Biomass+Utilization&rft.pages=559-566&rft.date=1983&rft_id=info%3Adoi%2F10.1007%2F978-1-4757-0833-2_30&rft.isbn=978-1-4757-0835-6&rft.aulast=Goldstein&rft.aufirst=Irving+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrolysis" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1041539562">.mw-parser-output .citation{word-wrap:break-word}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}</style><span class="citation patent" id="CITEREFFaroneCuzens1998"><a rel="nofollow" class="external text" href="https://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=US5726046">US 5726046</a>, Farone, William A. & Cuzens, John E., "Method of producing sugars using strong acid hydrolysis", published 1998-03-10,  assigned to Arkenol Inc.</span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Apatent&rft.number=5726046&rft.cc=US&rft.title=Method+of+producing+sugars+using+strong+acid+hydrolysis&rft.inventor=Farone&rft.assignee=Arkenol+Inc.&rft.pubdate=1998-03-10"><span style="display: none;"> </span></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVaughnRobbins1975" class="citation journal cs1">Vaughn, H. L.; Robbins, M. D. (April 1975). "Rapid procedure for the hydrolysis of amides to acids". <i>The Journal of Organic Chemistry</i>. <b>40</b> (8): 1187–1189. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00896a050">10.1021/jo00896a050</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=Rapid+procedure+for+the+hydrolysis+of+amides+to+acids&rft.volume=40&rft.issue=8&rft.pages=1187-1189&rft.date=1975-04&rft_id=info%3Adoi%2F10.1021%2Fjo00896a050&rft.aulast=Vaughn&rft.aufirst=H.+L.&rft.au=Robbins%2C+M.+D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrolysis" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://chem.libretexts.org/Courses/Georgia_Southern_University/CHEM_1152%3A_Survey_of_Chemistry_II_(GSU_-_Dr._Osborne)/05%3A_Organic_Chemical_Reactions/5.04%3A_Hydrolysis_Reactions">"5.4: Hydrolysis Reactions"</a>. <i>Chemistry LibreTexts</i>. 2021-08-04<span class="reference-accessdate">. Retrieved <span class="nowrap">2023-10-07</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Chemistry+LibreTexts&rft.atitle=5.4%3A+Hydrolysis+Reactions&rft.date=2021-08-04&rft_id=https%3A%2F%2Fchem.libretexts.org%2FCourses%2FGeorgia_Southern_University%2FCHEM_1152%253A_Survey_of_Chemistry_II_%28GSU_-_Dr._Osborne%29%2F05%253A_Organic_Chemical_Reactions%2F5.04%253A_Hydrolysis_Reactions&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrolysis" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChen2015" class="citation book cs1">Chen, Hongzheng (2015). <i>Lignocellulose Biorefinery Engineering</i>. Woodhead Publishing. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-100135-6" title="Special:BookSources/978-0-08-100135-6"><bdi>978-0-08-100135-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Lignocellulose+Biorefinery+Engineering&rft.pub=Woodhead+Publishing&rft.date=2015&rft.isbn=978-0-08-100135-6&rft.aulast=Chen&rft.aufirst=Hongzheng&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrolysis" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPandeyLarrocheRickeDussap2011" class="citation book cs1">Pandey; Larroche; Ricke; Dussap; Gnansounou (2011). <i>Biofuels: Alternaative Feedstocks and Conversion Processes</i>. Academic press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-385099-7" title="Special:BookSources/978-0-12-385099-7"><bdi>978-0-12-385099-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Biofuels%3A+Alternaative+Feedstocks+and+Conversion+Processes&rft.pub=Academic+press&rft.date=2011&rft.isbn=978-0-12-385099-7&rft.au=Pandey&rft.au=Larroche&rft.au=Ricke&rft.au=Dussap&rft.au=Gnansounou&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrolysis" class="Z3988"></span></span> </li> <li id="cite_note-mcmurry-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-mcmurry_17-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMcMurry1996" class="citation book cs1">McMurry, John (1996). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/organicchemistry00mcmu/page/820"><i>Organic Chemistry</i></a></span> (4th ed.). Pacific Grove, CA: Brooks/Cole Publishing Company. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/organicchemistry00mcmu/page/820">820–821</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0534238327" title="Special:BookSources/0534238327"><bdi>0534238327</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+Chemistry&rft.place=Pacific+Grove%2C+CA&rft.pages=820-821&rft.edition=4th&rft.pub=Brooks%2FCole+Publishing+Company&rft.date=1996&rft.isbn=0534238327&rft.aulast=McMurry&rft.aufirst=John&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Forganicchemistry00mcmu%2Fpage%2F820&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrolysis" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output 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