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id="toc-Unsaturated_carbon_centres-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> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>External links</span> </div> </a> <ul id="toc-External_links-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" 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substitution</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 32 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-32" 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">32 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%A7%D8%B3%D8%AA%D8%A8%D8%AF%D8%A7%D9%84_%D9%85%D8%AD%D8%A8_%D9%84%D9%84%D9%86%D9%88%D8%A7%D8%A9" title="استبدال محب للنواة – Arabic" lang="ar" hreflang="ar" data-title="استبدال محب للنواة" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Nukleofilik_%C9%99v%C9%99zetm%C9%99_reaksiyalar%C4%B1" title="Nukleofilik əvəzetmə reaksiyaları – Azerbaijani" lang="az" hreflang="az" data-title="Nukleofilik əvəzetmə reaksiyaları" 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%95%E0%A7%87%E0%A6%A8%E0%A7%8D%E0%A6%A6%E0%A7%8D%E0%A6%B0%E0%A6%BE%E0%A6%95%E0%A6%B0%E0%A7%8D%E0%A6%B7%E0%A7%80_%E0%A6%AA%E0%A7%8D%E0%A6%B0%E0%A6%A4%E0%A6%BF%E0%A6%B8%E0%A7%8D%E0%A6%A5%E0%A6%BE%E0%A6%AA%E0%A6%A8" title="কেন্দ্রাকর্ষী প্রতিস্থাপন – Bangla" lang="bn" hreflang="bn" data-title="কেন্দ্রাকর্ষী প্রতিস্থাপন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Nukleofilna_supstitucija" title="Nukleofilna supstitucija – Bosnian" lang="bs" hreflang="bs" data-title="Nukleofilna supstitucija" 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/Substituci%C3%B3_nucle%C3%B2fila" title="Substitució nucleòfila – Catalan" lang="ca" hreflang="ca" data-title="Substitució nucleòfila" 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/Nukleofiln%C3%AD_substituce" title="Nukleofilní substituce – Czech" lang="cs" hreflang="cs" data-title="Nukleofilní substituce" 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/Nukleofil_substitution" title="Nukleofil substitution – Danish" lang="da" hreflang="da" data-title="Nukleofil substitution" 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/Nukleophile_Substitution" title="Nukleophile Substitution – German" lang="de" hreflang="de" data-title="Nukleophile Substitution" 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/Nukleofiilne_asendusreaktsioon" title="Nukleofiilne asendusreaktsioon – Estonian" lang="et" hreflang="et" data-title="Nukleofiilne asendusreaktsioon" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Sustituci%C3%B3n_nucle%C3%B3fila" title="Sustitución nucleófila – Spanish" lang="es" hreflang="es" data-title="Sustitución nucleófila" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AC%D8%A7%D9%86%D8%B4%DB%8C%D9%86%DB%8C_%D9%87%D8%B3%D8%AA%D9%87%E2%80%8C%D8%AF%D9%88%D8%B3%D8%AA%DB%8C" title="جانشینی هسته‌دوستی – Persian" lang="fa" hreflang="fa" data-title="جانشینی هسته‌دوستی" 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/Substitution_nucl%C3%A9ophile" title="Substitution nucléophile – French" lang="fr" hreflang="fr" data-title="Substitution nucléophile" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%B9%9C%ED%95%B5%EC%84%B1_%EC%B9%98%ED%99%98" title="친핵성 치환 – Korean" lang="ko" hreflang="ko" data-title="친핵성 치환" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Substitusi_nukleofilik" title="Substitusi nukleofilik – Indonesian" lang="id" hreflang="id" data-title="Substitusi nukleofilik" 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/Sostituzione_nucleofila" title="Sostituzione nucleofila – Italian" lang="it" hreflang="it" data-title="Sostituzione nucleofila" 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%AA%D7%9E%D7%A8%D7%94_%D7%A0%D7%95%D7%A7%D7%9C%D7%90%D7%95%D7%A4%D7%99%D7%9C%D7%99%D7%AA" title="התמרה נוקלאופילית – Hebrew" lang="he" hreflang="he" data-title="התמרה נוקלאופילית" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Nukleofil_szubsztit%C3%BAci%C3%B3" title="Nukleofil szubsztitúció – Hungarian" lang="hu" hreflang="hu" data-title="Nukleofil szubsztitúció" 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%9D%D1%83%D0%BA%D0%BB%D0%B5%D0%BE%D1%84%D0%B8%D0%BB%D0%BD%D0%B0_%D1%81%D1%83%D0%BF%D1%81%D1%82%D0%B8%D1%82%D1%83%D1%86%D0%B8%D1%98%D0%B0" title="Нуклеофилна супституција – Macedonian" lang="mk" hreflang="mk" data-title="Нуклеофилна супституција" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Penukargantian_nukleofilik" title="Penukargantian nukleofilik – Malay" lang="ms" hreflang="ms" data-title="Penukargantian nukleofilik" 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-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Nucleofiele_substitutie" title="Nucleofiele substitutie – Dutch" lang="nl" hreflang="nl" data-title="Nucleofiele substitutie" 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/%E6%B1%82%E6%A0%B8%E7%BD%AE%E6%8F%9B%E5%8F%8D%E5%BF%9C" title="求核置換反応 – Japanese" lang="ja" hreflang="ja" data-title="求核置換反応" 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/Nukleofil_substitusjon" title="Nukleofil substitusjon – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Nukleofil substitusjon" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Substytucja_nukleofilowa" title="Substytucja nukleofilowa – Polish" lang="pl" hreflang="pl" data-title="Substytucja nukleofilowa" 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/Substitui%C3%A7%C3%A3o_nucleof%C3%ADlica" title="Substituição nucleofílica – Portuguese" lang="pt" hreflang="pt" data-title="Substituição nucleofílica" 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/Substitu%C8%9Bie_nucleofil%C4%83" title="Substituție nucleofilă – Romanian" lang="ro" hreflang="ro" data-title="Substituție nucleofilă" 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%A0%D0%B5%D0%B0%D0%BA%D1%86%D0%B8%D0%B8_%D0%BD%D1%83%D0%BA%D0%BB%D0%B5%D0%BE%D1%84%D0%B8%D0%BB%D1%8C%D0%BD%D0%BE%D0%B3%D0%BE_%D0%B7%D0%B0%D0%BC%D0%B5%D1%89%D0%B5%D0%BD%D0%B8%D1%8F" title="Реакции нуклеофильного замещения – Russian" lang="ru" hreflang="ru" data-title="Реакции нуклеофильного замещения" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Nucleophilic_substitution" title="Nucleophilic substitution – Simple English" lang="en-simple" hreflang="en-simple" data-title="Nucleophilic substitution" 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/Nukleofiln%C3%A1_substit%C3%BAcia" title="Nukleofilná substitúcia – Slovak" lang="sk" hreflang="sk" data-title="Nukleofilná substitúcia" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Nukleofiilinen_substituutio" title="Nukleofiilinen substituutio – Finnish" lang="fi" hreflang="fi" data-title="Nukleofiilinen substituutio" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/N%C3%BCkleofil_yer_de%C4%9Fi%C5%9Ftirme_tepkimeleri" title="Nükleofil yer değiştirme tepkimeleri – Turkish" lang="tr" hreflang="tr" data-title="Nükleofil yer değiştirme tepkimeleri" 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%A0%D0%B5%D0%B0%D0%BA%D1%86%D1%96%D1%97_%D0%BD%D1%83%D0%BA%D0%BB%D0%B5%D0%BE%D1%84%D1%96%D0%BB%D1%8C%D0%BD%D0%BE%D0%B3%D0%BE_%D0%B7%D0%B0%D0%BC%D1%96%D1%89%D0%B5%D0%BD%D0%BD%D1%8F" title="Реакції нуклеофільного заміщення – Ukrainian" lang="uk" hreflang="uk" data-title="Реакції нуклеофільного заміщення" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a 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class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></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">Chemical reaction in which a nucleophile is affixed to the substrate</div> <p>In <a href="/wiki/Chemistry" title="Chemistry">chemistry</a>, a <b>nucleophilic substitution</b> (<b>S<sub>N</sub></b>) is a class of <a href="/wiki/Chemical_reaction" title="Chemical reaction">chemical reactions</a> in which an <a href="/wiki/Electron" title="Electron">electron</a>-rich <a href="/wiki/Chemical_species" title="Chemical species">chemical species</a> (known as a <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a>) replaces a <a href="/wiki/Functional_group" title="Functional group">functional group</a> within another electron-deficient molecule (known as the <a href="/wiki/Electrophile" title="Electrophile">electrophile</a>). The molecule that contains the electrophile and the leaving functional group is called the <a href="/wiki/Substrate_(chemistry)" title="Substrate (chemistry)">substrate</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><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>The most general form of the reaction may be given as the following: </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 {\text{Nuc}}\mathbf {:} +{\ce {R-LG -> R-Nuc}}+{\text{LG}}\mathbf {:} }"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>Nuc</mtext> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo mathvariant="bold">:</mo> </mrow> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>LG</mtext> <mo stretchy="false">⟶</mo> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>Nuc</mtext> </mrow> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <mtext>LG</mtext> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo mathvariant="bold">:</mo> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\text{Nuc}}\mathbf {:} +{\ce {R-LG -> R-Nuc}}+{\text{LG}}\mathbf {:} }</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/c2ab382ee064b237c1950108f447b5f8f9c472a3" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:33.989ex; height:2.343ex;" alt="{\displaystyle {\text{Nuc}}\mathbf {:} +{\ce {R-LG -> R-Nuc}}+{\text{LG}}\mathbf {:} }"></span></dd></dl> <p>The electron pair (<b>:</b>) from the nucleophile (Nuc) <a href="https://en.wiktionary.org/wiki/attack#Verb" class="extiw" title="wiktionary:attack">attacks</a> the substrate (<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">R−LG</span>) and bonds with it. Simultaneously, the leaving group (LG) departs with an electron pair. The principal product in this case is <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−Nuc</span>. The nucleophile may be electrically neutral or negatively charged, whereas the substrate is typically neutral or positively charged. </p><p>An example of nucleophilic substitution is the <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> of an <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> <a href="/wiki/Bromide" title="Bromide">bromide</a>, R-Br under basic conditions, where the attacking nucleophile is <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">OH<sup class="template-chem2-sup">−</sup></span>) and the <a href="/wiki/Leaving_group" title="Leaving group">leaving group</a> is <a href="/wiki/Bromide" title="Bromide">bromide</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Br<sup class="template-chem2-sup">−</sup></span>). </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 {OH- + R-Br -> R-OH + Br-}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msup> <mtext>OH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </msup> <mo>+</mo> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>Br</mtext> <mo stretchy="false">⟶</mo> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>OH</mtext> <mo>+</mo> <msup> <mtext>Br</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </msup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {OH- + R-Br -> R-OH + Br-}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/5e9ef2ee7a0fd4625d748b85eb95684e4fbc0bf7" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:33.053ex; height:2.676ex;" alt="{\displaystyle {\ce {OH- + R-Br -> R-OH + Br-}}}"></span></dd></dl> <p>Nucleophilic substitution reactions are common in <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>. Nucleophiles often attack a <a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">saturated</a> <a href="/wiki/Aliphatic" class="mw-redirect" title="Aliphatic">aliphatic</a> carbon. Less often, they may attack an <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> or unsaturated carbon.<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="Saturated_carbon_centres">Saturated carbon centres</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nucleophilic_substitution&action=edit&section=1" title="Edit section: Saturated carbon centres"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="SN1_and_SN2_reactions">S<sub>N</sub>1 and S<sub>N</sub>2 reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nucleophilic_substitution&action=edit&section=2" title="Edit section: SN1 and SN2 reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Sn2_Sn1_Graph_en.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/0/05/Sn2_Sn1_Graph_en.png" decoding="async" width="300" height="300" class="mw-file-element" data-file-width="300" data-file-height="300" /></a><figcaption>A graph showing the relative reactivities of the different alkyl halides towards S<sub>N</sub>1 and S<sub>N</sub>2 reactions (also see Table 1).</figcaption></figure> <p>In 1935, <a href="/wiki/Edward_D._Hughes" class="mw-redirect" title="Edward D. Hughes">Edward D. Hughes</a> and <a href="/wiki/Christopher_Kelk_Ingold" title="Christopher Kelk Ingold">Sir Christopher Ingold</a> studied nucleophilic substitution reactions of <a href="/wiki/Alkyl_halide" class="mw-redirect" title="Alkyl halide">alkyl halides</a> and related compounds. They proposed that there were two main mechanisms at work, both of them competing with each other. The two main mechanisms were the <a href="/wiki/SN1_reaction" title="SN1 reaction">S<sub>N</sub>1 reaction</a> and the <a href="/wiki/SN2_reaction" title="SN2 reaction">S<sub>N</sub>2 reaction</a>, where <i>S</i> stands for substitution, <i>N</i> stands for nucleophilic, and the number represents the <a href="/wiki/Order_(chemistry)" class="mw-redirect" title="Order (chemistry)">kinetic order</a> of the reaction.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>In the S<sub>N</sub>2 reaction, the addition of the nucleophile and the elimination of leaving group take place simultaneously (i.e. a <a href="/wiki/Concerted_reaction" title="Concerted reaction">concerted reaction</a>). S<sub>N</sub>2 occurs when the central carbon atom is easily accessible to the nucleophile.<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> </p> <table align="center" class="wikitable"> <tbody><tr> <th colspan="2">Nucleophilic substitution at carbon </th></tr> <tr> <td bgcolor="#FFFFFF"><span typeof="mw:File"><a href="/wiki/File:Sn2EtCl%2Bbromide.png" class="mw-file-description" title="mechanism"><img alt="mechanism" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Sn2EtCl%2Bbromide.png/340px-Sn2EtCl%2Bbromide.png" decoding="async" width="340" height="91" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Sn2EtCl%2Bbromide.png/510px-Sn2EtCl%2Bbromide.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Sn2EtCl%2Bbromide.png/680px-Sn2EtCl%2Bbromide.png 2x" data-file-width="1247" data-file-height="334" /></a></span> </td></tr> <tr> <td bgcolor="#FFFFFF"><span typeof="mw:File"><a href="/wiki/File:Sn2_reaction.gif" class="mw-file-description" title="SN2 reaction of CH3Cl and Cl-"><img alt="SN2 reaction of CH3Cl and Cl-" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/18/Sn2_reaction.gif/400px-Sn2_reaction.gif" decoding="async" width="400" height="204" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/1/18/Sn2_reaction.gif 1.5x" data-file-width="500" data-file-height="255" /></a></span> </td></tr> <tr> <td><a href="/wiki/SN2" class="mw-redirect" title="SN2">S<sub>N</sub>2 mechanism</a> </td></tr></tbody></table> <p>In S<sub>N</sub>2 reactions, there are a few conditions that affect the rate of the reaction. First of all, the 2 in S<sub>N</sub>2 implies that there are two concentrations of substances that affect the rate of reaction: substrate (Sub) and nucleophile. The rate equation for this reaction would be Rate=k[Sub][Nuc]. For a S<sub>N</sub>2 reaction, an <a href="/wiki/Protic_solvent" title="Protic solvent">aprotic solvent</a> is best, such as acetone, DMF, or DMSO. Aprotic solvents do not add protons (H<sup>+</sup> ions) into solution; if protons were present in S<sub>N</sub>2 reactions, they would react with the nucleophile and severely limit the reaction rate. Since this reaction occurs in one step, <a href="/wiki/Steric_effects" title="Steric effects">steric effects</a> drive the reaction speed. In the intermediate step, the nucleophile is 185 degrees from the leaving group and the stereochemistry is inverted as the nucleophile bonds to make the product. Also, because the intermediate is partially bonded to the nucleophile and leaving group, there is no time for the substrate to rearrange itself: the nucleophile will bond to the same carbon that the leaving group was attached to. A final factor that affects reaction rate is nucleophilicity; the nucleophile must attack an atom other than a hydrogen. </p><p>By contrast the S<sub>N</sub>1 reaction involves two steps. S<sub>N</sub>1 reactions tend to be important when the central carbon atom of the substrate is surrounded by bulky groups, both because such groups interfere sterically with the S<sub>N</sub>2 reaction (discussed above) and because a highly substituted carbon forms a stable <a href="/wiki/Carbocation" title="Carbocation">carbocation</a>. </p> <table align="center" class="wikitable"> <tbody><tr> <th colspan="2">Nucleophilic substitution at carbon </th></tr> <tr> <td bgcolor="#FFFFFF"><span typeof="mw:File"><a href="/wiki/File:SN1_reaction_mechanism.png" class="mw-file-description" title="SN1 reaction mechanism"><img alt="SN1 reaction mechanism" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/SN1_reaction_mechanism.png/300px-SN1_reaction_mechanism.png" decoding="async" width="300" height="133" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/SN1_reaction_mechanism.png/450px-SN1_reaction_mechanism.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bb/SN1_reaction_mechanism.png/600px-SN1_reaction_mechanism.png 2x" data-file-width="1074" data-file-height="476" /></a></span> </td></tr> <tr> <td><a href="/wiki/SN1" class="mw-redirect" title="SN1">S<sub>N</sub>1 mechanism</a> </td></tr></tbody></table> <p>Like S<sub>N</sub>2 reactions, there are quite a few factors that affect the reaction rate of S<sub>N</sub>1 reactions. Instead of having two concentrations that affect the reaction rate, there is only one, substrate. The rate equation for this would be Rate=k[Sub]. Since the rate of a reaction is only determined by its slowest step, the rate at which the leaving group "leaves" determines the speed of the reaction. This means that the better the leaving group, the faster the reaction rate. A general rule for what makes a good leaving group is the weaker the conjugate base, the better the leaving group. In this case, halogens are going to be the best leaving groups, while compounds such as amines, hydrogen, and alkanes are going to be quite poor leaving groups. As S<sub>N</sub>2 reactions were affected by sterics, S<sub>N</sub>1 reactions are determined by bulky groups attached to the carbocation. Since there is an intermediate that actually contains a positive charge, bulky groups attached are going to help stabilize the charge on the carbocation through resonance and distribution of charge. In this case, tertiary carbocation will react faster than a secondary which will react much faster than a primary. It is also due to this carbocation intermediate that the product does not have to have inversion. The nucleophile can attack from the top or the bottom and therefore create a racemic product. It is important to use a protic solvent, water and alcohols, since an aprotic solvent could attack the intermediate and cause unwanted product. It does not matter if the hydrogens from the protic solvent react with the nucleophile since the nucleophile is not involved in the rate determining step. </p> <table class="wikitable" width="800px"> <tbody><tr> <th colspan="8">Table 1. Nucleophilic substitutions on RX (an alkyl halide or equivalent) </th></tr> <tr> <td colspan="1">Factor </td> <th colspan="1"><a href="/wiki/SN1_reaction" title="SN1 reaction">S<sub>N</sub>1</a> </th> <th colspan="1"><a href="/wiki/SN2_reaction" title="SN2 reaction">S<sub>N</sub>2</a> </th> <th colspan="1">Comments </th></tr> <tr> <td><a href="/wiki/Chemical_kinetics" title="Chemical kinetics">Kinetics</a></td> <td>Rate = k[RX]</td> <td>Rate = k[RX][Nuc] </td></tr> <tr> <td><a href="/wiki/Primary_alkyl" class="mw-redirect" title="Primary alkyl">Primary alkyl</a></td> <td>Never unless additional stabilising groups present</td> <td>Good unless a hindered nucleophile is used</td> <td> </td></tr> <tr> <td><a href="/wiki/Secondary_alkyl" class="mw-redirect" title="Secondary alkyl">Secondary alkyl</a></td> <td>Moderate</td> <td>Moderate</td> <td> </td></tr> <tr> <td><a href="/wiki/Tertiary_alkyl" class="mw-redirect" title="Tertiary alkyl">Tertiary alkyl</a></td> <td>Excellent</td> <td>Never</td> <td><a href="/wiki/Elimination_reaction" title="Elimination reaction">Elimination</a> likely if heated or if strong base used </td></tr> <tr> <td><a href="/wiki/Leaving_group" title="Leaving group">Leaving group</a></td> <td>Important</td> <td>Important</td> <td>For halogens,<br />I > Br > Cl >> F </td></tr> <tr> <td><a href="/wiki/Nucleophilicity" class="mw-redirect" title="Nucleophilicity">Nucleophilicity</a></td> <td>Unimportant</td> <td>Important</td> <td> </td></tr> <tr> <td>Preferred <a href="/wiki/Solvent" title="Solvent">solvent</a></td> <td><a href="/wiki/Chemical_polarity" title="Chemical polarity">Polar</a> <a href="/wiki/Protic" class="mw-redirect" title="Protic">protic</a></td> <td>Polar <a href="/wiki/Aprotic" class="mw-redirect" title="Aprotic">aprotic</a></td> <td> </td></tr> <tr> <td><a href="/wiki/Stereochemistry" title="Stereochemistry">Stereochemistry</a></td> <td><a href="/wiki/Racemisation" class="mw-redirect" title="Racemisation">Racemisation</a> (+ partial <a href="/wiki/Stereochemistry" title="Stereochemistry">inversion</a> possible)</td> <td>Inversion</td> <td> </td></tr> <tr> <td><a href="/wiki/Carbocation_rearrangement" class="mw-redirect" title="Carbocation rearrangement">Rearrangements</a></td> <td>Common</td> <td>Rare</td> <td>Side reaction </td></tr> <tr> <td><a href="/wiki/Elimination_reaction" title="Elimination reaction">Eliminations</a></td> <td>Common, especially with basic nucleophiles</td> <td>Only with heat & basic nucleophiles</td> <td>Side reaction<br /> esp. if heated </td></tr> </tbody></table> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nucleophilic_substitution&action=edit&section=3" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There are many reactions in organic chemistry involving this type of mechanism. Common examples include: </p> <ul><li><a href="/wiki/Organic_reduction" class="mw-redirect" title="Organic reduction">Organic reductions</a> with <a href="/wiki/Hydride" title="Hydride">hydrides</a>, for example</li></ul> <dl><dd><dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><a href="/wiki/Alkyl_halide" class="mw-redirect" title="Alkyl halide">R−X</a> → <a href="/wiki/Alkane" title="Alkane">R−H</a></span> using <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride">LiAlH<sub class="template-chem2-sub">4</sub></a></span>   (S<sub>N</sub>2)</dd></dl></dd></dl> <ul><li><a href="/wiki/Hydrolysis" title="Hydrolysis">Hydrolysis</a> reactions such as</li></ul> <dl><dd><dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−Br + OH<sup class="template-chem2-sup">−</sup> → <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">R−OH</a> + <a href="/wiki/Bromide" title="Bromide">Br<sup class="template-chem2-sup">−</sup></a></span> (S<sub>N</sub>2) or</dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−Br + H<sub class="template-chem2-sub">2</sub>O → R−OH + <a href="/wiki/Hydrobromic_acid" title="Hydrobromic acid">HBr</a></span>   (S<sub>N</sub>1)</dd></dl></dd></dl> <ul><li><a href="/wiki/Williamson_ether_synthesis" title="Williamson ether synthesis">Williamson ether synthesis</a></li></ul> <dl><dd><dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−Br + <a href="/wiki/Alkoxide" title="Alkoxide">OR'<sup class="template-chem2-sup">−</sup></a> → <a href="/wiki/Ether" title="Ether">R−OR'</a> + Br<sup class="template-chem2-sup">−</sup></span>   (S<sub>N</sub>2)</dd></dl></dd></dl> <ul><li>The <a href="/wiki/Wenker_synthesis" title="Wenker synthesis">Wenker synthesis</a>, a ring-closing reaction of aminoalcohols.</li> <li>The <a href="/wiki/Finkelstein_reaction" title="Finkelstein reaction">Finkelstein reaction</a>, a halide exchange reaction. Phosphorus nucleophiles appear in the <a href="/wiki/Perkow_reaction" title="Perkow reaction">Perkow reaction</a> and the <a href="/wiki/Michaelis%E2%80%93Arbuzov_reaction" title="Michaelis–Arbuzov reaction">Michaelis–Arbuzov reaction</a>.</li> <li>The <a href="/wiki/Kolbe_nitrile_synthesis" title="Kolbe nitrile synthesis">Kolbe nitrile synthesis</a>, the reaction of alkyl halides with cyanides.</li></ul> <div class="mw-heading mw-heading3"><h3 id="Borderline_mechanism">Borderline mechanism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nucleophilic_substitution&action=edit&section=4" title="Edit section: Borderline mechanism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>An example of a substitution reaction taking place by a so-called <b>borderline mechanism</b> as originally studied by Hughes and Ingold<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> is the reaction of <i>1-phenylethyl chloride</i> with <a href="/wiki/Sodium_methoxide" title="Sodium methoxide">sodium methoxide</a> in methanol. </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:1-phenylethylchloride_methanolysis.svg" class="mw-file-description" title="1-phenylethylchloride methanolysis"><img alt="1-phenylethylchloride methanolysis" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/1-phenylethylchloride_methanolysis.svg/329px-1-phenylethylchloride_methanolysis.svg.png" decoding="async" width="329" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/1-phenylethylchloride_methanolysis.svg/494px-1-phenylethylchloride_methanolysis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/1-phenylethylchloride_methanolysis.svg/658px-1-phenylethylchloride_methanolysis.svg.png 2x" data-file-width="329" data-file-height="100" /></a></span></dd></dl> <p>The <a href="/wiki/Reaction_rate" title="Reaction rate">reaction rate</a> is found to the sum of S<sub>N</sub>1 and S<sub>N</sub>2 components with 61% (3,5 M, 70 °C) taking place by the latter. </p> <div class="mw-heading mw-heading3"><h3 id="Other_mechanisms">Other mechanisms</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nucleophilic_substitution&action=edit&section=5" title="Edit section: Other mechanisms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Besides S<sub>N</sub>1 and S<sub>N</sub>2, other mechanisms are known, although they are less common. The <b><a href="/wiki/SNi" title="SNi">S<sub>N</sub>i</a></b> mechanism is observed in reactions of <a href="/wiki/Thionyl_chloride" title="Thionyl chloride">thionyl chloride</a> with <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a>, and it is similar to S<sub>N</sub>1 except that the nucleophile is delivered from the same side as the leaving group. </p><p>Nucleophilic substitutions can be accompanied by an <a href="/wiki/Allylic_rearrangement" title="Allylic rearrangement">allylic rearrangement</a> as seen in reactions such as the <a href="/wiki/Ferrier_rearrangement" title="Ferrier rearrangement">Ferrier rearrangement</a>. This type of mechanism is called an S<sub>N</sub>1' or S<sub>N</sub>2' reaction (depending on the kinetics). With <a href="/wiki/Allyl" class="mw-redirect" title="Allyl">allylic</a> halides or sulphonates, for example, the nucleophile may attack at the γ unsaturated carbon in place of the carbon bearing the leaving group. This may be seen in the reaction of 1-chloro-2-butene with <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> to give a mixture of 2-buten-1-ol and 1-buten-3-ol: </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 {CH3CH=CH-CH2-Cl -> CH3CH=CH-CH2-OH + CH3CH(OH)-CH=CH2}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>Cl</mtext> <mo stretchy="false">⟶</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>OH</mtext> <mo>+</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>OH</mtext> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </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 {CH3CH=CH-CH2-Cl -> CH3CH=CH-CH2-OH + CH3CH(OH)-CH=CH2}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/c4ab9fd25a08faaf707b7c850234945d9f551b40" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:81.018ex; height:3.009ex;" alt="{\displaystyle {\ce {CH3CH=CH-CH2-Cl -> CH3CH=CH-CH2-OH + CH3CH(OH)-CH=CH2}}}"></span></dd></dl> <p>The <a href="/wiki/Sn1CB_mechanism" class="mw-redirect" title="Sn1CB mechanism">Sn1CB mechanism</a> appears in <a href="/wiki/Inorganic_chemistry" title="Inorganic chemistry">inorganic chemistry</a>. Competing mechanisms exist.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><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> </p><p>In <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic chemistry</a> the <a href="/wiki/Nucleophilic_abstraction" title="Nucleophilic abstraction">nucleophilic abstraction</a> reaction occurs with a nucleophilic substitution mechanism. </p> <div class="mw-heading mw-heading2"><h2 id="Unsaturated_carbon_centres">Unsaturated carbon centres</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nucleophilic_substitution&action=edit&section=6" title="Edit section: Unsaturated carbon centres"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nucleophilic substitution via the S<sub>N</sub>1 or S<sub>N</sub>2 mechanism does not generally occur with vinyl or aryl halides or related compounds. Under certain conditions nucleophilic substitutions may occur, via other mechanisms such as those described in the <a href="/wiki/Nucleophilic_aromatic_substitution" title="Nucleophilic aromatic substitution">nucleophilic aromatic substitution</a> article. </p><p>Substitution can occur at the <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> group, such as <a href="/wiki/Acyl_chloride" title="Acyl chloride">acyl chlorides</a> and <a href="/wiki/Ester" title="Ester">esters</a>. </p> <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=Nucleophilic_substitution&action=edit&section=7" 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 reflist-columns references-column-width reflist-columns-2"> <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"><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><cite id="CITEREFMarch1992" class="citation book cs1">March, J. (1992). <i>Advanced Organic Chemistry</i> (4th ed.). New York: Wiley. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780471601807" title="Special:BookSources/9780471601807"><bdi>9780471601807</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry&rft.place=New+York&rft.edition=4th&rft.pub=Wiley&rft.date=1992&rft.isbn=9780471601807&rft.aulast=March&rft.aufirst=J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANucleophilic+substitution" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text">R. A. Rossi, R. H. de Rossi, <i>Aromatic Substitution by the S<sub>RN</sub>1 Mechanism, ACS Monograph Series No. 178, American Chemical Society, 1983. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-8412-0648-1" title="Special:BookSources/0-8412-0648-1">0-8412-0648-1</a>.</i></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">L. G. Wade, <i>Organic Chemistry</i>, 5th ed., Prentice Hall, Upper Saddle River, New Jersey, 2003.</span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text">S. R. Hartshorn, <i>Aliphatic Nucleophilic Substitution</i>, Cambridge University Press, London, 1973. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-521-09801-7" title="Special:BookSources/0-521-09801-7">0-521-09801-7</a></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"><i>Introducing Aliphatic Substitution with a Discovery Experiment Using Competing Electrophiles</i> Timothy P. Curran, Amelia J. Mostovoy, Margaret E. Curran, and Clara Berger Journal of Chemical Education 2016 93 (4), 757-761 <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/10.1021%2Facs.jchemed.5b00394">10.1021/acs.jchemed.5b00394</a> </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"><i>253. Reaction kinetics and the Walden inversion. Part II. Homogeneous hydrolysis, alcoholysis, and ammonolysis of -phenylethyl halides</i> Edward D. Hughes, Christopher K. Ingold and Alan D. Scott, <a href="/wiki/J._Chem._Soc." class="mw-redirect" title="J. Chem. Soc.">J. Chem. Soc.</a>, <b>1937</b>, 1201 <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/10.1039%2FJR9370001201">10.1039/JR9370001201</a></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text">N.S.Imyanitov. <i>Electrophilic Bimolecular Substitution as an Alternative to Nucleophilic Monomolecular Substitution in Inorganic and Organic Chemistry</i>. J. Gen. Chem. USSR (Engl. Transl.) <b>1990</b>; 60 (3); 417-419.</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">Unimolecular Nucleophilic Substitution does not Exist! / N.S.Imyanitov. <a rel="nofollow" class="external text" href="http://sciteclibrary.ru/eng/catalog/pages/9330.html">SciTecLibrary</a></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Nucleophilic_substitution&action=edit&section=8" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid 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aria-labelledby="Basic_reaction_mechanisms" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Reaction_mechanisms" title="Template:Reaction mechanisms"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Reaction_mechanisms" title="Template talk:Reaction mechanisms"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Reaction_mechanisms" title="Special:EditPage/Template:Reaction mechanisms"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Basic_reaction_mechanisms" style="font-size:114%;margin:0 4em">Basic <a href="/wiki/Reaction_mechanism" title="Reaction mechanism">reaction mechanisms</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Nucleophilic substitutions</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/SN1_reaction" title="SN1 reaction">Unimolecular nucleophilic substitution</a> (S<sub>N</sub>1)</li> <li><a href="/wiki/SN2_reaction" title="SN2 reaction">Bimolecular nucleophilic substitution</a> (S<sub>N</sub>2)</li> <li><a href="/wiki/Nucleophilic_aromatic_substitution" title="Nucleophilic aromatic substitution">Nucleophilic aromatic substitution</a> (S<sub>N</sub>Ar)</li> <li><a href="/wiki/SNi" title="SNi">Nucleophilic internal substitution</a> (S<sub>N</sub>i)</li> <li><a href="/wiki/Nucleophilic_acyl_substitution" class="mw-redirect" title="Nucleophilic acyl substitution">Nucleophilic acyl substitution</a> (S<sub>N</sub>Acyl)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Electrophilic_substitution" title="Electrophilic substitution">Electrophilic substitutions</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Electrophilic_aromatic_substitution" title="Electrophilic aromatic substitution">Electrophilic aromatic substitution</a> (S<sub>E</sub>Ar)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Elimination_reaction" title="Elimination reaction">Elimination reactions</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/E1_elimination" class="mw-redirect" title="E1 elimination">Unimolecular elimination</a> (E1)</li> <li><a href="/wiki/E1cB-elimination_reaction" title="E1cB-elimination reaction">E1cB-elimination</a></li> <li><a href="/wiki/E2_elimination" class="mw-redirect" title="E2 elimination">Bimolecular elimination</a> (E2)</li> <li><a href="/wiki/Ei_mechanism" title="Ei mechanism">E<sub>i</sub> elimination</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Addition_reaction" title="Addition reaction">Addition reactions</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Electrophilic_addition" title="Electrophilic addition">Electrophilic addition</a> (A<sub>E</sub>)</li> <li><a href="/wiki/Nucleophilic_addition" title="Nucleophilic addition">Nucleophilic addition</a> (A<sub>N</sub>)</li> <li><a href="/wiki/Free-radical_addition" title="Free-radical addition">Free-radical addition</a></li> <li><a href="/wiki/Cycloaddition" title="Cycloaddition">Cycloaddition</a></li> <li><a href="/wiki/Oxidative_addition" title="Oxidative addition">Oxidative addition</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Unimolecular reactions</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Intramolecular_reaction" title="Intramolecular reaction">Intramolecular reaction</a></li> <li><a href="/wiki/Isomerization" title="Isomerization">Isomerization</a></li> <li><a href="/wiki/Photodissociation" title="Photodissociation">Photodissociation</a></li> <li><a href="/wiki/Lindemann%E2%80%93Hinshelwood_mechanism" class="mw-redirect" title="Lindemann–Hinshelwood mechanism">Lindemann–Hinshelwood mechanism</a></li> <li><a href="/wiki/RRKM_theory" title="RRKM theory">RRKM theory</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Electron_transfer" title="Electron transfer">Electron/Proton transfer</a> reactions</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Redox" title="Redox">Redox</a></li> <li><a href="/wiki/Harpoon_reaction" title="Harpoon reaction">Harpoon reaction</a></li> <li><a href="/wiki/Grotthuss_mechanism" title="Grotthuss mechanism">Grotthuss mechanism</a></li> <li><a href="/wiki/Marcus_theory" title="Marcus theory">Marcus theory</a></li> <li><a href="/wiki/Inner_sphere_electron_transfer" title="Inner sphere electron transfer">Inner sphere electron transfer</a></li> <li><a href="/wiki/Outer_sphere_electron_transfer" title="Outer sphere electron transfer">Outer sphere electron transfer</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Medium effects</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Solvent_effects" title="Solvent effects">Solvent effects</a></li> <li><a href="/wiki/Cage_effect" title="Cage effect">Cage effect</a></li> <li><a href="/wiki/Matrix_isolation" title="Matrix isolation">Matrix isolation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related topics</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Elementary_reaction" title="Elementary reaction">Elementary reaction</a></li> <li><a href="/wiki/Reaction_dynamics" title="Reaction dynamics">Reaction dynamics</a></li> <li><a href="/wiki/Reactive_intermediate" title="Reactive intermediate">Reactive intermediate</a></li> <li><a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">Radical (chemistry)</a></li> <li><a href="/wiki/Molecularity" title="Molecularity">Molecularity</a></li> <li><a href="/wiki/Stereochemistry" title="Stereochemistry">Stereochemistry</a></li> <li><a href="/wiki/Catalysis" title="Catalysis">Catalysis</a></li> <li><a href="/wiki/Collision_theory" title="Collision theory">Collision theory</a></li> <li><a href="/wiki/Arrow_pushing" title="Arrow pushing">Arrow pushing</a></li> <li><a href="/wiki/Potential_energy_surface" title="Potential energy surface">Potential energy surface</a></li> <li><a href="/wiki/More_O%27Ferrall%E2%80%93Jencks_plot" title="More O'Ferrall–Jencks plot">More O'Ferrall–Jencks plot</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chemical_kinetics" title="Chemical kinetics">Chemical kinetics</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Rate_equation" title="Rate equation">Rate equation</a></li> <li><a href="/wiki/Equilibrium_constant" title="Equilibrium constant">Equilibrium constant</a></li> <li><a href="/wiki/Rate-determining_step" title="Rate-determining step">Rate-determining step</a></li> <li><a href="/wiki/Reaction_coordinate" title="Reaction coordinate">Reaction coordinate</a></li> <li><a href="/wiki/Energy_profile_(chemistry)" title="Energy profile (chemistry)">Energy profile (chemistry)</a></li> <li><a href="/wiki/Transition_state_theory" title="Transition state theory">Transition state theory</a></li> <li><a href="/wiki/Activation_energy" title="Activation energy">Activation energy</a></li> <li><a href="/wiki/Activated_complex" title="Activated complex">Activated complex</a></li> <li><a href="/wiki/Arrhenius_equation" title="Arrhenius equation">Arrhenius equation</a></li> <li><a href="/wiki/Eyring_equation" title="Eyring equation">Eyring equation</a></li> <li><a href="/wiki/Michaelis%E2%80%93Menten_kinetics" title="Michaelis–Menten 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