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id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">Inhoud</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">naar zijbalk verplaatsen</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">verbergen</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">Top</div> </a> </li> <li id="toc-Historische_context" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Historische_context"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Historische context</span> </div> </a> <ul id="toc-Historische_context-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Anti-Markovnikov" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Anti-Markovnikov"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Anti-Markovnikov</span> </div> </a> <button aria-controls="toc-Anti-Markovnikov-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>Anti-Markovnikov-subkopje inklappen</span> </button> <ul id="toc-Anti-Markovnikov-sublist" class="vector-toc-list"> <li id="toc-Waterstof_is_niet_positief" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Waterstof_is_niet_positief"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Waterstof is niet positief</span> </div> </a> <ul id="toc-Waterstof_is_niet_positief-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Radicalen" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Radicalen"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Radicalen</span> </div> </a> <ul id="toc-Radicalen-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Katalysatoren" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Katalysatoren"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Katalysatoren</span> </div> </a> <ul id="toc-Katalysatoren-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Omleggingen" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Omleggingen"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Omleggingen</span> </div> </a> <ul id="toc-Omleggingen-sublist" class="vector-toc-list"> </ul> </li> </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="Inhoud" 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="Inhoudsopgave omschakelen" > <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">Inhoudsopgave omschakelen</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">Regel van Markovnikov</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="Ga naar een artikel in een andere taal. Beschikbaar in 41 talen" > <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-41" 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">41 talen</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/%D9%82%D8%A7%D8%B9%D8%AF%D8%A9_%D9%85%D8%A7%D8%B1%D9%83%D9%88%D9%81%D9%86%D9%8A%D9%83%D9%88%D9%81" title="قاعدة ماركوفنيكوف – Arabisch" lang="ar" hreflang="ar" data-title="قاعدة ماركوفنيكوف" data-language-autonym="العربية" data-language-local-name="Arabisch" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AE%E0%A6%BE%E0%A6%B0%E0%A7%8D%E0%A6%95%E0%A6%A8%E0%A6%BF%E0%A6%95%E0%A6%AD%E0%A7%87%E0%A6%B0_%E0%A6%A8%E0%A7%80%E0%A6%A4%E0%A6%BF" title="মার্কনিকভের নীতি – Bengaals" lang="bn" hreflang="bn" data-title="মার্কনিকভের নীতি" data-language-autonym="বাংলা" data-language-local-name="Bengaals" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Regla_de_Mark%C3%B3vnikov" title="Regla de Markóvnikov – Catalaans" lang="ca" hreflang="ca" data-title="Regla de Markóvnikov" data-language-autonym="Català" data-language-local-name="Catalaans" 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/Markovnikovovo_pravidlo" title="Markovnikovovo pravidlo – Tsjechisch" lang="cs" hreflang="cs" data-title="Markovnikovovo pravidlo" data-language-autonym="Čeština" data-language-local-name="Tsjechisch" 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/Markovnikovs_regel" title="Markovnikovs regel – Deens" lang="da" hreflang="da" data-title="Markovnikovs regel" data-language-autonym="Dansk" data-language-local-name="Deens" 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/Markownikow-Regel" title="Markownikow-Regel – Duits" lang="de" hreflang="de" data-title="Markownikow-Regel" data-language-autonym="Deutsch" data-language-local-name="Duits" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9A%CE%B1%CE%BD%CF%8C%CE%BD%CE%B1%CF%82_%CE%9C%CE%B1%CF%81%CE%BA%CF%8C%CE%B2%CE%BD%CE%B9%CE%BA%CE%BF%CF%86" title="Κανόνας Μαρκόβνικοφ – Grieks" lang="el" hreflang="el" data-title="Κανόνας Μαρκόβνικοφ" data-language-autonym="Ελληνικά" data-language-local-name="Grieks" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Markovnikov%27s_rule" title="Markovnikov's rule – Engels" lang="en" hreflang="en" data-title="Markovnikov's rule" data-language-autonym="English" data-language-local-name="Engels" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Regulo_de_Markovnikov" title="Regulo de Markovnikov – Esperanto" lang="eo" hreflang="eo" data-title="Regulo de Markovnikov" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Regla_de_Markovnikov" title="Regla de Markovnikov – Spaans" lang="es" hreflang="es" data-title="Regla de Markovnikov" data-language-autonym="Español" data-language-local-name="Spaans" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Markovnikovi_reegel" title="Markovnikovi reegel – Estisch" lang="et" hreflang="et" data-title="Markovnikovi reegel" data-language-autonym="Eesti" data-language-local-name="Estisch" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Markovnikoven_arau" title="Markovnikoven arau – Baskisch" lang="eu" hreflang="eu" data-title="Markovnikoven arau" data-language-autonym="Euskara" data-language-local-name="Baskisch" 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/%D9%82%D8%A7%D9%86%D9%88%D9%86_%D9%85%D8%A7%D8%B1%DA%A9%D9%88%D9%86%DB%8C%DA%A9%D9%88%D9%81" title="قانون مارکونیکوف – Perzisch" lang="fa" hreflang="fa" data-title="قانون مارکونیکوف" data-language-autonym="فارسی" data-language-local-name="Perzisch" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Markovnikovin_s%C3%A4%C3%A4nt%C3%B6" title="Markovnikovin sääntö – Fins" lang="fi" hreflang="fi" data-title="Markovnikovin sääntö" data-language-autonym="Suomi" data-language-local-name="Fins" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/R%C3%A8gle_de_Markovnikov" title="Règle de Markovnikov – Frans" lang="fr" hreflang="fr" data-title="Règle de Markovnikov" data-language-autonym="Français" data-language-local-name="Frans" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%9B%D7%9C%D7%9C_%D7%9E%D7%A8%D7%A7%D7%95%D7%91%D7%A0%D7%99%D7%A7%D7%95%D7%91" title="כלל מרקובניקוב – Hebreeuws" lang="he" hreflang="he" data-title="כלל מרקובניקוב" data-language-autonym="עברית" data-language-local-name="Hebreeuws" 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/Markovnyikov-szab%C3%A1ly" title="Markovnyikov-szabály – Hongaars" lang="hu" hreflang="hu" data-title="Markovnyikov-szabály" data-language-autonym="Magyar" data-language-local-name="Hongaars" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%84%D5%A1%D6%80%D5%AF%D5%B8%D5%BE%D5%B6%D5%AB%D5%AF%D5%B8%D5%BE%D5%AB_%D5%AF%D5%A1%D5%B6%D5%B8%D5%B6" title="Մարկովնիկովի կանոն – Armeens" lang="hy" hreflang="hy" data-title="Մարկովնիկովի կանոն" data-language-autonym="Հայերեն" data-language-local-name="Armeens" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Aturan_Markovnikov" title="Aturan Markovnikov – Indonesisch" lang="id" hreflang="id" data-title="Aturan Markovnikov" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesisch" 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/Regola_di_Markovnikov" title="Regola di Markovnikov – Italiaans" lang="it" hreflang="it" data-title="Regola di Markovnikov" data-language-autonym="Italiano" data-language-local-name="Italiaans" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%9E%E3%83%AB%E3%82%B3%E3%83%95%E3%83%8B%E3%82%B3%E3%83%95%E5%89%87" title="マルコフニコフ則 – Japans" lang="ja" hreflang="ja" data-title="マルコフニコフ則" data-language-autonym="日本語" data-language-local-name="Japans" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9C%D0%B0%D1%80%D0%BA%D0%BE%D0%B2%D0%BD%D0%B8%D0%BA%D0%BE%D0%B2_%D0%B5%D1%80%D0%B5%D0%B6%D0%B5%D1%81%D1%96" title="Марковников ережесі – Kazachs" lang="kk" hreflang="kk" data-title="Марковников ережесі" data-language-autonym="Қазақша" data-language-local-name="Kazachs" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%A7%88%EB%A5%B4%EC%BD%94%EB%B8%8C%EB%8B%88%EC%BD%94%ED%94%84%EC%9D%98_%EB%B2%95%EC%B9%99" title="마르코브니코프의 법칙 – Koreaans" lang="ko" hreflang="ko" data-title="마르코브니코프의 법칙" data-language-autonym="한국어" data-language-local-name="Koreaans" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9C%D0%B0%D1%80%D0%BA%D0%BE%D0%B2%D0%BD%D0%B8%D0%BA%D0%BE%D0%B2_%D1%8D%D1%80%D0%B5%D0%B6%D0%B5%D1%81%D0%B8" title="Марковников эрежеси – Kirgizisch" lang="ky" hreflang="ky" data-title="Марковников эрежеси" data-language-autonym="Кыргызча" data-language-local-name="Kirgizisch" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9C%D0%B0%D1%80%D0%BA%D0%BE%D0%B2%D0%BD%D0%B8%D0%BA%D0%BE%D0%B2%D0%BE_%D0%BF%D1%80%D0%B0%D0%B2%D0%B8%D0%BB%D0%BE" title="Марковниково правило – Macedonisch" lang="mk" hreflang="mk" data-title="Марковниково правило" data-language-autonym="Македонски" data-language-local-name="Macedonisch" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Markovnikovs_regel" title="Markovnikovs regel – Noors - Bokmål" lang="nb" hreflang="nb" data-title="Markovnikovs regel" data-language-autonym="Norsk bokmål" data-language-local-name="Noors - 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/Regu%C5%82a_Markownikowa" title="Reguła Markownikowa – Pools" lang="pl" hreflang="pl" data-title="Reguła Markownikowa" data-language-autonym="Polski" data-language-local-name="Pools" 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/Regra_de_Markovnikov" title="Regra de Markovnikov – Portugees" lang="pt" hreflang="pt" data-title="Regra de Markovnikov" data-language-autonym="Português" data-language-local-name="Portugees" 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/Regula_lui_Markovnikov" title="Regula lui Markovnikov – Roemeens" lang="ro" hreflang="ro" data-title="Regula lui Markovnikov" data-language-autonym="Română" data-language-local-name="Roemeens" 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%9F%D1%80%D0%B0%D0%B2%D0%B8%D0%BB%D0%BE_%D0%9C%D0%B0%D1%80%D0%BA%D0%BE%D0%B2%D0%BD%D0%B8%D0%BA%D0%BE%D0%B2%D0%B0" title="Правило Марковникова – Russisch" lang="ru" hreflang="ru" data-title="Правило Марковникова" data-language-autonym="Русский" data-language-local-name="Russisch" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Markovnikovo_pravilo" title="Markovnikovo pravilo – Servo-Kroatisch" lang="sh" hreflang="sh" data-title="Markovnikovo pravilo" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Servo-Kroatisch" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Markovnikov%27s_Rule" title="Markovnikov's Rule – Simple English" lang="en-simple" hreflang="en-simple" data-title="Markovnikov's Rule" 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/Markovnikovovo_pravidlo" title="Markovnikovovo pravidlo – Slowaaks" lang="sk" hreflang="sk" data-title="Markovnikovovo pravidlo" data-language-autonym="Slovenčina" data-language-local-name="Slowaaks" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%9C%D0%B0%D1%80%D0%BA%D0%BE%D0%B2%D0%BD%D0%B8%D0%BA%D0%BE%D0%B2%D1%99%D0%B5%D0%B2%D0%BE_%D0%BF%D1%80%D0%B0%D0%B2%D0%B8%D0%BB%D0%BE" title="Марковниковљево правило – Servisch" lang="sr" hreflang="sr" data-title="Марковниковљево правило" data-language-autonym="Српски / srpski" data-language-local-name="Servisch" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Markovnikovs_regel" title="Markovnikovs regel – Zweeds" lang="sv" hreflang="sv" data-title="Markovnikovs regel" data-language-autonym="Svenska" data-language-local-name="Zweeds" 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%AE%E0%AE%BE%E0%AE%B0%E0%AF%8D%E0%AE%95%E0%AF%8B%E0%AE%B5%E0%AF%8D%E0%AE%A9%E0%AE%BF%E0%AE%95%E0%AE%BE%E0%AE%B5%E0%AF%8D_%E0%AE%B5%E0%AE%BF%E0%AE%A4%E0%AE%BF" title="மார்கோவ்னிகாவ் விதி – Tamil" lang="ta" hreflang="ta" data-title="மார்கோவ்னிகாவ் விதி" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Markovnikov_kural%C4%B1" title="Markovnikov kuralı – Turks" lang="tr" hreflang="tr" data-title="Markovnikov kuralı" data-language-autonym="Türkçe" data-language-local-name="Turks" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/%D0%9C%D0%B0%D1%80%D0%BA%D0%BE%D0%B2%D0%BD%D0%B8%D0%BA%D0%BE%D0%B2_%D0%BA%D0%B0%D0%B3%D1%8B%D0%B9%D0%B4%D3%99%D1%81%D0%B5" title="Марковников кагыйдәсе – Tataars" lang="tt" hreflang="tt" data-title="Марковников кагыйдәсе" data-language-autonym="Татарча / tatarça" data-language-local-name="Tataars" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9F%D1%80%D0%B0%D0%B2%D0%B8%D0%BB%D0%BE_%D0%9C%D0%B0%D1%80%D0%BA%D0%BE%D0%B2%D0%BD%D0%B8%D0%BA%D0%BE%D0%B2%D0%B0" title="Правило Марковникова – Oekraïens" lang="uk" hreflang="uk" data-title="Правило Марковникова" data-language-autonym="Українська" data-language-local-name="Oekraïens" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Quy_t%E1%BA%AFc_Markovnikov" title="Quy tắc Markovnikov – Vietnamees" lang="vi" hreflang="vi" data-title="Quy tắc Markovnikov" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamees" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%A9%AC%E5%B0%94%E7%A7%91%E5%A4%AB%E5%B0%BC%E7%A7%91%E5%A4%AB%E8%A7%84%E5%88%99" title="马尔科夫尼科夫规则 – Chinees" lang="zh" hreflang="zh" data-title="马尔科夫尼科夫规则" data-language-autonym="中文" data-language-local-name="Chinees" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span 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class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Uiterlijk</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">naar zijbalk verplaatsen</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">verbergen</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">Uit Wikipedia, de vrije encyclopedie</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="nl" dir="ltr"><p>In de <a href="/wiki/Organische_chemie" title="Organische chemie">organische chemie</a> is de <b>regel van Markovnikov</b> (of <b>regel van Markownikoff)</b> de verwoording van een aantal waarnemingen bij reacties van <a href="/wiki/Alkeen" title="Alkeen">alkenen</a> met <a href="/wiki/Polair" class="mw-redirect" title="Polair">polaire</a> <a href="/wiki/Reagens" title="Reagens">reagentia</a> zoals <a href="/wiki/Waterstofchloride" title="Waterstofchloride">waterstofchloride</a> en <a href="/wiki/Waterstofbromide" title="Waterstofbromide">waterstofbromide</a>. De regel werd rond 1870 geformuleerd door de Russische scheikundige <a href="/wiki/Vladimir_Markovnikov" title="Vladimir Markovnikov">Vladimir Markovnikov</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-Hughes_2-0" class="reference"><a href="#cite_note-Hughes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Samen met de regel van Markovnikov vormt de <a href="/wiki/Regel_van_Zajtsev" title="Regel van Zajtsev">regel van Zajtsev</a> een <a href="/wiki/Fenomenologie" title="Fenomenologie">fenomenologische</a> beschrijving van de reactie van alkenen met waterstofhalogeniden of de vorming van alkenen onder afstaan van een waterstofhalogenide. </p><p>De regel van Markovnikov luidt: </p> <style data-mw-deduplicate="TemplateStyles:r58633982">.mw-parser-output .cquote{margin:1.5em 0;padding:0 50px;display:table;position:relative;border-left:none}.mw-parser-output .cquote>:nth-last-child(2){margin-bottom:0}.mw-parser-output .cquote-cite{position:relative;margin:20px -40px 0;text-align:right;font-size:90%}.mw-parser-output .cquote-cite-leeg{margin-top:0}.mw-parser-output .cquote>:first-child::before,.mw-parser-output .cquote-cite::after{color:#B2B7F2;font-size:42px;font-family:"Times New Roman",Times,serif;font-weight:bold;position:absolute}.mw-parser-output .cquote>:first-child::before{content:"“";left:10px;top:-19px}.mw-parser-output .cquote-cite::after{content:"”";right:0;top:-53px;height:0}.mw-parser-output .cquote-cite-leeg::after{top:-33px}</style> <blockquote class="cquote"> <p>Bij de additie van een verbinding H-X aan een alkeen zal het <a href="/wiki/Waterstofatoom" title="Waterstofatoom">waterstofatoom</a> gebonden worden aan het koolstofatoom dat al de meeste waterstofatomen heeft, de groep X zal gebonden worden aan het koolstofatoom met de minste waterstofatomen.<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> <div class="cquote-cite cquote-cite-leeg"></div> </blockquote> <p>De regel van Markovnikov wordt geïllustreerd door de reactie van <a href="/wiki/Propeen" title="Propeen">propeen</a> met <a href="/wiki/Waterstofbromide" title="Waterstofbromide">waterstofbromide</a>: </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/Bestand:MarkovnikovRulePropeneHBr.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b1/MarkovnikovRulePropeneHBr.svg/514px-MarkovnikovRulePropeneHBr.svg.png" decoding="async" width="514" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b1/MarkovnikovRulePropeneHBr.svg/771px-MarkovnikovRulePropeneHBr.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b1/MarkovnikovRulePropeneHBr.svg/1028px-MarkovnikovRulePropeneHBr.svg.png 2x" data-file-width="514" data-file-height="129" /></a><figcaption></figcaption></figure> <p><a href="/wiki/2-broompropaan" title="2-broompropaan">2-broompropaan</a> is hier het voornaamste <a href="/wiki/Reactieproduct" title="Reactieproduct">reactieproduct</a>, in overeenstemming met de regel van Markovnikov. </p><p>Markovnikov formuleerde zijn regel op basis van de reactie van waterstofhalogeniden met alkenen (de <a href="/wiki/Hydrohalogenering" title="Hydrohalogenering">hydrohalogenering</a>). De regel bleek ook op te gaan voor de grote groep verbindingen met (gedeeltelijk) positief geladen waterstofatomen zoals water en <a href="/wiki/Alcohol_(stofklasse)" title="Alcohol (stofklasse)">alcoholen</a>, waarbij dan alcoholen (met de OH-groep aan het koolstofatoom met de minste waterstofatomen) respectievelijk <a href="/wiki/Ether_(scheikunde)" title="Ether (scheikunde)">ethers</a> gevormd werden. </p><p>De verklaring voor de regel kon Markovnikov nog niet geven omdat de ideeën rond de structuur van <a href="/wiki/Molecule" class="mw-redirect" title="Molecule">moleculen</a> en <a href="/wiki/Chemische_reactie" title="Chemische reactie">reacties</a> in 1870 nog niet ver genoeg ontwikkeld waren. Tegenwoordig kunnen we de waarneming verklaren via de vorming van het meest stabiele <a href="/wiki/Carbokation" title="Carbokation">carbokation</a> als <a href="/wiki/Overgangstoestand" title="Overgangstoestand">overgangstoestand</a> in de additie. Tijdens de additie wordt waterstof als positief ion aan een van de <a href="/wiki/Atoom" title="Atoom">atomen</a> van een <a href="/wiki/Dubbele_binding_(scheikunde)" title="Dubbele binding (scheikunde)">dubbele binding</a> overgedragen. De elektronen van de dubbele binding verzorgen de binding zodat een positieve lading op het andere koolstofatoom van de dubbele binding ontstaat. Hierdoor ontstaat een carbokation. Hoe meer koolstofatomen, of elektrondonerende groepen, aan het positieve koolstofatoom gebonden zijn, hoe stabieler het carbokation is. Het hoofdproduct van de reactie zal gevormd worden via het meest stabiele carbokation. Hierdoor zal het hoofdproduct van de additie van HX (waarbij X een willekeurig atoom / atoomgroep is die elektronegatiever is dan waterstof) aan een alkeen waterstof aan het minder gesubstitueerde en X aan de meer gesubstitueerde koolstofatoom hebben. Bewust is sprake van <b>hoofdproduct</b>: het minder stabiele carbokation wordt ook gevormd, en het reactieproduct ervan, H en X precies andersom aan het alkeen gebonden dus ook. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Historische_context">Historische context</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Regel_van_Markovnikov&veaction=edit&section=1" title="Bewerk dit kopje: Historische context" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Regel_van_Markovnikov&action=edit&section=1" title="De broncode bewerken van de sectie: Historische context"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Een van de reacties waarop Markovnikov zijn regel baseerde was de in 1865 beschreven additie van <a href="/wiki/Waterstofjodide" title="Waterstofjodide">waterstofjodide</a> aan <a href="/w/index.php?title=Broometheen&action=edit&redlink=1" class="new" title="Broometheen (de pagina bestaat niet)">broometheen</a>. Bij een andere gelegenheid werd het tussenproduct niet geïsoleerd maar de reactie ervan met vochtig <a href="/wiki/Zilver(I)oxide" title="Zilver(I)oxide">Ag<sub>2</sub>O</a> leverde <a href="/wiki/Aceetaldehyde" title="Aceetaldehyde">aceetaldehyde</a>, waarmee wel de koppeling van het halogeenatoom aan het koolstofatoom dat al een halogeen had aangetoond werd. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/Bestand:Markovnikov_original_reaction.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Markovnikov_original_reaction.png/500px-Markovnikov_original_reaction.png" decoding="async" width="500" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Markovnikov_original_reaction.png/750px-Markovnikov_original_reaction.png 1.5x, //upload.wikimedia.org/wikipedia/commons/3/3e/Markovnikov_original_reaction.png 2x" data-file-width="966" data-file-height="143" /></a><figcaption></figcaption></figure> <p>De regel werd voor het eerst in 1869 gepubliceerd, maar het duurde 60 jaar voor de chemische gemeenschap de regel ook als zodanig accepteerde. Mogelijk is dit het gevolg van het feit dat de regel als een voetnoot van liefst 4 pagina's in een artikel van 26 pagina's was opgenomen. Bovendien was veel van het experimentele werk dat als onderbouwing genoemd werd niet Markovnikovs eigen werk<sup id="cite_ref-Hughes_2-1" class="reference"><a href="#cite_note-Hughes-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>. </p> <div class="mw-heading mw-heading2"><h2 id="Anti-Markovnikov">Anti-Markovnikov</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Regel_van_Markovnikov&veaction=edit&section=2" title="Bewerk dit kopje: Anti-Markovnikov" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Regel_van_Markovnikov&action=edit&section=2" title="De broncode bewerken van de sectie: Anti-Markovnikov"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In een aantal gevallen gaat de regel van Markovnikov niet op. Er wordt dan gesproken van <b>anti-Markovnikov</b>-additie. Er kunnen verschillende reden zijn waarom afwijkingen optreden. </p> <div class="mw-heading mw-heading3"><h3 id="Waterstof_is_niet_positief">Waterstof is niet positief</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Regel_van_Markovnikov&veaction=edit&section=3" title="Bewerk dit kopje: Waterstof is niet positief" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Regel_van_Markovnikov&action=edit&section=3" title="De broncode bewerken van de sectie: Waterstof is niet positief"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>De additie van <a href="/wiki/Boraan_(stofklasse)" title="Boraan (stofklasse)">boranen</a> aan dubbele bindingen (<a href="/wiki/Hydroboratie" class="mw-redirect" title="Hydroboratie">hydroboratie</a>) verloopt naar de letter van de regel omgekeerd: <a href="/wiki/Boor_(element)" title="Boor (element)">boor</a> aan het koolstofatoom met de meeste waterstofatomen en waterstof aan het koolstofatoom dat de minste waterstofatomen had. Het mechanisme, de vorming van een intermediair carbokation is echter gelijk, het verschil wordt gevormd door het feit dat waterstof elektronegatiever is dan boor. Na koppeling van het positieve - boor - deel van het molecule aan het alkeen koppelt het <a href="/wiki/Hydride" title="Hydride">hydride</a> met het gevormde carbokation. </p> <div class="mw-heading mw-heading3"><h3 id="Radicalen">Radicalen</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Regel_van_Markovnikov&veaction=edit&section=4" title="Bewerk dit kopje: Radicalen" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Regel_van_Markovnikov&action=edit&section=4" title="De broncode bewerken van de sectie: Radicalen"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Reacties die niet via een carbokation verlopen maar via een <a href="/wiki/Radicaal_(scheikunde)" title="Radicaal (scheikunde)">radicaal</a> gedragen zich tegenovergesteld aan de Markovnikov-regel. Het halogeen koppelt eerst aan het alkeen, en die eerste koppeling van het reagens is weer op het koolstofatoom dat de meeste waterstofatomen draagt: ook voor radicalen geldt dat hoe meer substituenten hoe stabieler het radicaal. </p> <div class="mw-heading mw-heading3"><h3 id="Katalysatoren">Katalysatoren</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Regel_van_Markovnikov&veaction=edit&section=5" title="Bewerk dit kopje: Katalysatoren" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Regel_van_Markovnikov&action=edit&section=5" title="De broncode bewerken van de sectie: Katalysatoren"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Onder invloed van <a href="/wiki/Katalysator" title="Katalysator">katalysatoren</a> kan de additie ook omgekeerd verlopen: <a href="/wiki/Hydratatie" title="Hydratatie">hydratatie</a> van <a href="/wiki/Fenylacetyleen" title="Fenylacetyleen">fenylacetyleen</a> met <a href="/wiki/Goud" title="Goud">goud</a> als katalysator levert het Markovnikov-product: <a href="/wiki/Acetofenon" title="Acetofenon">acetofenon</a>. Met een speciale <a href="/wiki/Ruthenium" title="Ruthenium">ruthenium</a>-houdende katalysator (<i>in situ</i> gemaakt uit <a href="/w/index.php?title=Ruthenoceen&action=edit&redlink=1" class="new" title="Ruthenoceen (de pagina bestaat niet)">ruthenoceen</a> met <a href="/wiki/Cyclopentadienyl" title="Cyclopentadienyl">cyclopentadienyl</a>, <a href="/wiki/Naftaleen" title="Naftaleen">naftaleen</a> en <a href="/wiki/Pyridine" title="Pyridine">pyridine</a>-<a href="/wiki/Ligand" title="Ligand">liganden</a>) levert het andere isomeer: <a href="/w/index.php?title=2-fenylacetaldehyde&action=edit&redlink=1" class="new" title="2-fenylacetaldehyde (de pagina bestaat niet)">2-fenylacetaldehyde</a><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> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/Bestand:Antimarkovnikovhydration.png" class="mw-file-description" title="Anti-Markovnikov hydratatie"><img alt="Anti-Markovnikov hydratatie" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Antimarkovnikovhydration.png/500px-Antimarkovnikovhydration.png" decoding="async" width="500" height="251" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Antimarkovnikovhydration.png/750px-Antimarkovnikovhydration.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Antimarkovnikovhydration.png/1000px-Antimarkovnikovhydration.png 2x" data-file-width="1016" data-file-height="511" /></a><figcaption>Anti-Markovnikov hydratatie</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Omleggingen">Omleggingen</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Regel_van_Markovnikov&veaction=edit&section=6" title="Bewerk dit kopje: Omleggingen" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Regel_van_Markovnikov&action=edit&section=6" title="De broncode bewerken van de sectie: Omleggingen"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anti-Markovnikov gedrag komt ook soms tot uiting in <a href="/wiki/Omleggingsreactie" class="mw-redirect" title="Omleggingsreactie">omleggingsreacties</a>: na de eerste reactie treedt zeer snel een wijziging op in het molecule, zo snel dat het eerste product eigenlijk niet geïsoleerd kan worden. In een door <a href="/wiki/Titanium(IV)chloride" title="Titanium(IV)chloride">titanium(IV)chloride</a> gekatalyseerde, formeel als <a href="/wiki/Nucleofiele_substitutie" title="Nucleofiele substitutie">nucleofiele substitutie</a> beschreven reactie, van <a href="/wiki/Optisch_zuiver" class="mw-redirect" title="Optisch zuiver">optisch zuiver</a> <b>1</b> in het schema hieronder, worden twee <a href="/wiki/Racemisch" class="mw-redirect" title="Racemisch">racemische</a> producten gevormd: <b>2a</b> and <b>2b</b><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> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/Bestand:AntiMarkovnikovRearrangement.png" class="mw-file-description" title="Anti-Markovnikov omlegging"><img alt="Anti-Markovnikov omlegging" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/AntiMarkovnikovRearrangement.png/500px-AntiMarkovnikovRearrangement.png" decoding="async" width="500" height="298" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/AntiMarkovnikovRearrangement.png/750px-AntiMarkovnikovRearrangement.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ec/AntiMarkovnikovRearrangement.png/1000px-AntiMarkovnikovRearrangement.png 2x" data-file-width="1015" data-file-height="605" /></a><figcaption>Anti-Markovnikov omlegging</figcaption></figure> <p>Het ontstaan van de verschillende producten kan verklaard worden door aan te nemen dat de <a href="/wiki/Hydroxylgroep" title="Hydroxylgroep">hydroxy-groep</a> uit <b>1</b> aanleiding geeft tot het tertiaire carbokation <b>A</b>, dat vervolgens omlegt naar het schijnbaar minder stabiele ion <b>B</b>. Chloor kan vervolgens vanaf twee verschillende kanten dit positieve ion benaderen, waarbij de waargenomen reactieproducten ontstaan. </p> <div class="toccolours appendix" role="presentation" style="font-size:90%; margin:1em 0 -0.5em; clear:both;"> <div><span style="font-weight:bold">Bronnen, noten en/of referenties</span></div> <div class="reflist" style="list-style-type: decimal;"><div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><a href="#cite_ref-1">↑</a></span> <span class="reference-text"><span class="citation" id="CITEREFW._Markownikoff1870"><span style="font-variant:small-caps;">W. Markownikoff</span> (1870). <cite>Ueber die Abhängigkeit der verschiedenen Vertretbarkeit des Radicalwasserstoffs in den isomeren Buttersäuren</cite>. <i>Annalen der Pharmacie</i> <b>153</b> (1): 228–259. <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>: <a rel="nofollow" class="external text" href="https://doi.org/10.1002/jlac.18701530204">10.1002/jlac.18701530204</a>. </span></span> </li> <li id="cite_note-Hughes-2"><span class="mw-cite-backlink">↑ <a href="#cite_ref-Hughes_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Hughes_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><i>Was Markovnikov’s Rule an Inspired Guess?</i> Peter Hughes 1152 Journal of Chemical Education • Vol. 83 No. 8 August <b>2006</b></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.personal.psu.edu/the1/addregi.htm">Additions to Alkenes: Regiochemistry</a></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text"><i>Highly Active in Situ Catalysts for Anti-Markovnikov Hydration of Terminal Alkynes</i>Aurélie Labonne, Thomas Kribber, and Lukas Hintermann <a href="/w/index.php?title=Org._Lett.&action=edit&redlink=1" class="new" title="Org. Lett. (de pagina bestaat niet)">Org. Lett.</a>; <b>2006</b>; 8(25) pp 5853 - 5856; (Letter) <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1021%2Fol062455k">10.1021/ol062455k</a></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text"><i>TiCl4 Induced Anti-Markovnikov Rearrangement</i> Mugio Nishizawa, Yumiko Asai, and Hiroshi Imagawa <a href="/w/index.php?title=Org._Lett.&action=edit&redlink=1" class="new" title="Org. Lett. (de pagina bestaat niet)">Org. Lett.</a>; <b>2006</b>; 8(25) pp 5793 - 5796; (Letter) <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1021%2Fol062337x">10.1021/ol062337x</a>.</span> </li> </ol></div></div> </div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Overgenomen van "<a dir="ltr" href="https://nl.wikipedia.org/w/index.php?title=Regel_van_Markovnikov&oldid=63234829">https://nl.wikipedia.org/w/index.php?title=Regel_van_Markovnikov&oldid=63234829</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Categorie:Alles" title="Categorie:Alles">Categorieën</a>: <ul><li><a href="/wiki/Categorie:Fysische_organische_chemie" title="Categorie:Fysische organische chemie">Fysische organische chemie</a></li><li><a href="/wiki/Categorie:Chemische_reactiviteit" title="Categorie:Chemische reactiviteit">Chemische reactiviteit</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> Deze pagina is voor het laatst bewerkt op 4 nov 2022 om 14:37.</li> <li id="footer-info-copyright">De tekst is beschikbaar onder de licentie <a rel="nofollow" class="external text" href="//creativecommons.org/licenses/by-sa/4.0/deed.nl">Creative Commons Naamsvermelding/Gelijk delen</a>, er kunnen aanvullende voorwaarden van toepassing zijn. 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