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Halogenácia – Wikipédia

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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">Obsah</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">presunúť do postranného panelu</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">skryť</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">Začiatok</div> </a> </li> <li id="toc-Halogenácia_v_organickej_chémii" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Halogenácia_v_organickej_chémii"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Halogenácia v organickej chémii</span> </div> </a> <button aria-controls="toc-Halogenácia_v_organickej_chémii-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>Přepnout podsekci Halogenácia v organickej chémii</span> </button> <ul id="toc-Halogenácia_v_organickej_chémii-sublist" class="vector-toc-list"> <li id="toc-Aromatická_halogenácia" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Aromatická_halogenácia"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Aromatická halogenácia</span> </div> </a> <ul id="toc-Aromatická_halogenácia-sublist" class="vector-toc-list"> <li id="toc-Fluorácia" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Fluorácia"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1.1</span> <span>Fluorácia</span> </div> </a> <ul id="toc-Fluorácia-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chlorácia" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Chlorácia"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1.2</span> <span>Chlorácia</span> </div> </a> <ul id="toc-Chlorácia-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bromácia" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Bromácia"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1.3</span> <span>Bromácia</span> </div> </a> <ul id="toc-Bromácia-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Jodácia" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Jodácia"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1.4</span> <span>Jodácia</span> </div> </a> <ul id="toc-Jodácia-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Referencie" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Referencie"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Referencie</span> </div> </a> <ul id="toc-Referencie-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pozri_aj" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Pozri_aj"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Pozri aj</span> </div> </a> <ul id="toc-Pozri_aj-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="Obsah" 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="Prepnúť obsah" > <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">Prepnúť obsah</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">Halogenácia</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="Prejsť na článok v inom jazyku. Je dostupný v 38 jazykoch" > <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-38" 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">38 jazykov</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%87%D9%84%D8%AC%D9%86%D8%A9" title="هلجنة – arabčina" lang="ar" hreflang="ar" data-title="هلجنة" data-language-autonym="العربية" data-language-local-name="arabčina" 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%B9%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B2%E0%A7%8B%E0%A6%9C%E0%A7%87%E0%A6%A8_%E0%A6%B8%E0%A6%82%E0%A6%AF%E0%A7%8B%E0%A6%97_%E0%A6%AC%E0%A6%BF%E0%A6%95%E0%A7%8D%E0%A6%B0%E0%A6%BF%E0%A6%AF%E0%A6%BC%E0%A6%BE" title="হ্যালোজেন সংযোগ বিক্রিয়া – bengálčina" lang="bn" hreflang="bn" data-title="হ্যালোজেন সংযোগ বিক্রিয়া" data-language-autonym="বাংলা" data-language-local-name="bengálčina" 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/Halogenaci%C3%B3" title="Halogenació – katalánčina" lang="ca" hreflang="ca" data-title="Halogenació" data-language-autonym="Català" data-language-local-name="katalánčina" 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/Halogenace" title="Halogenace – čeština" lang="cs" hreflang="cs" data-title="Halogenace" data-language-autonym="Čeština" data-language-local-name="čeština" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Halogenierung" title="Halogenierung – nemčina" lang="de" hreflang="de" data-title="Halogenierung" data-language-autonym="Deutsch" data-language-local-name="nemčina" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Halogenation" title="Halogenation – angličtina" lang="en" hreflang="en" data-title="Halogenation" data-language-autonym="English" data-language-local-name="angličtina" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Halogenaci%C3%B3n" title="Halogenación – španielčina" lang="es" hreflang="es" data-title="Halogenación" data-language-autonym="Español" data-language-local-name="španielčina" 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/Halogeenimine" title="Halogeenimine – estónčina" lang="et" hreflang="et" data-title="Halogeenimine" data-language-autonym="Eesti" data-language-local-name="estónčina" 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/Halogenazio" title="Halogenazio – baskičtina" lang="eu" hreflang="eu" data-title="Halogenazio" data-language-autonym="Euskara" data-language-local-name="baskičtina" 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%87%D8%A7%D9%84%D9%88%DA%98%D9%86%E2%80%8C%D8%AF%D8%A7%D8%B1_%DA%A9%D8%B1%D8%AF%D9%86" title="هالوژن‌دار کردن – perzština" lang="fa" hreflang="fa" data-title="هالوژن‌دار کردن" data-language-autonym="فارسی" data-language-local-name="perzština" 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/Halogenointi" title="Halogenointi – fínčina" lang="fi" hreflang="fi" data-title="Halogenointi" data-language-autonym="Suomi" data-language-local-name="fínčina" 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/Halog%C3%A9nation" title="Halogénation – francúzština" lang="fr" hreflang="fr" data-title="Halogénation" data-language-autonym="Français" data-language-local-name="francúzština" 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%94%D7%9C%D7%95%D7%92%D7%A0%D7%A6%D7%99%D7%94" title="הלוגנציה – hebrejčina" lang="he" hreflang="he" data-title="הלוגנציה" data-language-autonym="עברית" data-language-local-name="hebrejčina" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B9%E0%A5%88%E0%A4%B2%E0%A5%8B%E0%A4%9C%E0%A4%A8%E0%A4%A8" title="हैलोजनन – hindčina" lang="hi" hreflang="hi" data-title="हैलोजनन" data-language-autonym="हिन्दी" data-language-local-name="hindčina" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Halogeniranje" title="Halogeniranje – chorvátčina" lang="hr" hreflang="hr" data-title="Halogeniranje" data-language-autonym="Hrvatski" data-language-local-name="chorvátčina" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Halog%C3%A9nez%C3%A9s" title="Halogénezés – maďarčina" lang="hu" hreflang="hu" data-title="Halogénezés" data-language-autonym="Magyar" data-language-local-name="maďarčina" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Halogenasi" title="Halogenasi – indonézština" lang="id" hreflang="id" data-title="Halogenasi" data-language-autonym="Bahasa Indonesia" data-language-local-name="indonézština" 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/Alogenazione" title="Alogenazione – taliančina" lang="it" hreflang="it" data-title="Alogenazione" data-language-autonym="Italiano" data-language-local-name="taliančina" 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%8F%E3%83%AD%E3%82%B2%E3%83%B3%E5%8C%96" title="ハロゲン化 – japončina" lang="ja" hreflang="ja" data-title="ハロゲン化" data-language-autonym="日本語" data-language-local-name="japončina" 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%93%D0%B0%D0%BB%D0%BE%D0%B3%D0%B5%D0%BD%D0%B4%D0%B5%D1%83" title="Галогендеу – kazaština" lang="kk" hreflang="kk" data-title="Галогендеу" data-language-autonym="Қазақша" data-language-local-name="kazaština" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Halogenatioun" title="Halogenatioun – luxemburčina" lang="lb" hreflang="lb" data-title="Halogenatioun" data-language-autonym="Lëtzebuergesch" data-language-local-name="luxemburčina" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Halogen%C4%93%C5%A1ana" title="Halogenēšana – lotyština" lang="lv" hreflang="lv" data-title="Halogenēšana" data-language-autonym="Latviešu" data-language-local-name="lotyština" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Penghalogenan" title="Penghalogenan – malajčina" lang="ms" hreflang="ms" data-title="Penghalogenan" data-language-autonym="Bahasa Melayu" data-language-local-name="malajčina" 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/Halogenering" title="Halogenering – holandčina" lang="nl" hreflang="nl" data-title="Halogenering" data-language-autonym="Nederlands" data-language-local-name="holandčina" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Halogenering" title="Halogenering – nórčina (bokmal)" lang="nb" hreflang="nb" data-title="Halogenering" data-language-autonym="Norsk bokmål" data-language-local-name="nórčina (bokmal)" 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/Halogenowanie" title="Halogenowanie – poľština" lang="pl" hreflang="pl" data-title="Halogenowanie" data-language-autonym="Polski" data-language-local-name="poľština" 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/Halogena%C3%A7%C3%A3o" title="Halogenação – portugalčina" lang="pt" hreflang="pt" data-title="Halogenação" data-language-autonym="Português" data-language-local-name="portugalčina" 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/Halogenare" title="Halogenare – rumunčina" lang="ro" hreflang="ro" data-title="Halogenare" data-language-autonym="Română" data-language-local-name="rumunčina" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%93%D0%B0%D0%BB%D0%BE%D0%B3%D0%B5%D0%BD%D0%B8%D1%80%D0%BE%D0%B2%D0%B0%D0%BD%D0%B8%D0%B5" title="Галогенирование – ruština" lang="ru" hreflang="ru" data-title="Галогенирование" data-language-autonym="Русский" data-language-local-name="ruština" 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/Halogenacija" title="Halogenacija – srbochorvátčina" lang="sh" hreflang="sh" data-title="Halogenacija" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="srbochorvátčina" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Kloriranje" title="Kloriranje – slovinčina" lang="sl" hreflang="sl" data-title="Kloriranje" data-language-autonym="Slovenščina" data-language-local-name="slovinčina" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A5%D0%B0%D0%BB%D0%BE%D0%B3%D0%B5%D0%BD%D0%B0%D1%86%D0%B8%D1%98%D0%B0" title="Халогенација – srbčina" lang="sr" hreflang="sr" data-title="Халогенација" data-language-autonym="Српски / srpski" data-language-local-name="srbčina" 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/Halogenering" title="Halogenering – švédčina" lang="sv" hreflang="sv" data-title="Halogenering" data-language-autonym="Svenska" data-language-local-name="švédčina" 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%86%E0%AE%B2%E0%AE%9A%E0%AE%A9%E0%AF%87%E0%AE%B1%E0%AF%8D%E0%AE%B1%E0%AE%AE%E0%AF%8D" title="ஆலசனேற்றம் – tamilčina" lang="ta" hreflang="ta" data-title="ஆலசனேற்றம்" data-language-autonym="தமிழ்" data-language-local-name="tamilčina" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D2%B2%D0%BE%D0%BB%D1%83%D0%B6%D0%B5%D0%BD%D0%B4%D0%BE%D1%80_%D0%BA%D0%B0%D1%80%D0%B4%D0%B0%D0%BD" title="Ҳолужендор кардан – tadžičtina" lang="tg" hreflang="tg" data-title="Ҳолужендор 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class="vector-appearance vector-pinnable-element"> <div 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">Vzhľad</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">presunúť do postranného panelu</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">skryť</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">z Wikipédie, slobodnej encyklopédie</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="sk" dir="ltr"><figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/S%C3%BAbor:Prim-Halogenalkan.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a7/Prim-Halogenalkan.svg/220px-Prim-Halogenalkan.svg.png" decoding="async" width="220" height="53" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a7/Prim-Halogenalkan.svg/330px-Prim-Halogenalkan.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a7/Prim-Halogenalkan.svg/440px-Prim-Halogenalkan.svg.png 2x" data-file-width="108" data-file-height="26" /></a><figcaption>Organické zlúčeniny obsahujúce halogén (všeobecne značený X, ako na obrázku) vznikajú halogenáciou.</figcaption></figure> <p><b>Halogenácia</b> je <a href="/wiki/Chemick%C3%A1_reakcia" title="Chemická reakcia">chemická reakcia</a>, počas ktorej dochádza k zabudovaniu atómu <a href="/wiki/Halog%C3%A9n" title="Halogén">halogénu</a> do <a href="/wiki/Organick%C3%A1_zl%C3%BA%C4%8Denina" title="Organická zlúčenina">organickej molekuly</a>.<sup id="cite_ref-:0_1-0" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-:1_2-0" class="reference"><a href="#cite_note-:1-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-:3_4-0" class="reference"><a href="#cite_note-:3-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> V priebehu reakcie dochádza buď k zámene atómu <a href="/wiki/Vod%C3%ADk" title="Vodík">vodíka</a> za atóm halogénu, <a href="/wiki/Ad%C3%ADcia_(ch%C3%A9mia)" title="Adícia (chémia)">adícii</a> <a href="/wiki/Halogenovod%C3%ADk" title="Halogenovodík">halogenovodíkov</a> či halogénov na <a href="/w/index.php?title=Nenas%C3%BDten%C3%A1_zl%C3%BA%C4%8Denina&amp;action=edit&amp;redlink=1" class="new" title="Nenasýtená zlúčenina (stránka neexistuje)">nenasýtené organické zlúčeniny</a> alebo náhrade <a href="/wiki/Hydroxylov%C3%A1_skupina" title="Hydroxylová skupina">hydroxylovej skupiny</a> pomocou halogenačných činidiel<sup id="cite_ref-:0_1-1" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> (napríklad <a href="/wiki/Chlorid_fosfore%C4%8Dn%C3%BD" title="Chlorid fosforečný">PCl<sub>5</sub></a>, <a href="/w/index.php?title=Chlorid_fosforylu&amp;action=edit&amp;redlink=1" class="new" title="Chlorid fosforylu (stránka neexistuje)">POCl<sub>3</sub></a> alebo <a href="/w/index.php?title=Chlorid_tionylu&amp;action=edit&amp;redlink=1" class="new" title="Chlorid tionylu (stránka neexistuje)">SOCl<sub>2</sub></a><sup id="cite_ref-:0_1-2" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup>). Tento názov sa niekedy používa i na označenie reakcií, pri ktorých dochádza k naviazaniu halogénu do <a href="/wiki/Anorganick%C3%A1_zl%C3%BA%C4%8Denina" title="Anorganická zlúčenina">anorganických zlúčenín</a>.<sup id="cite_ref-:1_2-1" class="reference"><a href="#cite_note-:1-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-:2_6-0" class="reference"><a href="#cite_note-:2-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup> Obdobne možno pojmom halogenácia označiť aj <a href="/w/index.php?title=Chemick%C3%A1_synt%C3%A9za&amp;action=edit&amp;redlink=1" class="new" title="Chemická syntéza (stránka neexistuje)">syntetické metódy</a> využívané na halogenačné reakcie.<sup id="cite_ref-:2_6-1" class="reference"><a href="#cite_note-:2-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> </p><p>V závislosti od druhu halogénu sa halogenácia označuje aj ako <b>fluorácia</b> (<a href="/wiki/Flu%C3%B3r" title="Fluór">fluór</a>), <b>chlorácia</b> (<a href="/wiki/Chl%C3%B3r" title="Chlór">chlór</a>), <b>bromácia</b> (<a href="/wiki/Br%C3%B3m" title="Bróm">bróm</a>) alebo <b>jodácia</b> (<a href="/wiki/J%C3%B3d" title="Jód">jód</a>).<sup id="cite_ref-:0_1-3" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-:3_4-1" class="reference"><a href="#cite_note-:3-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> Chlorácia a bromácia prebiehajú podobnými všeobecnými metódami, zatiaľ čo fluorácia a jodácia vyžadujú špecializované metódy.<sup id="cite_ref-:2_6-2" class="reference"><a href="#cite_note-:2-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Halogenácia_v_organickej_chémii"><span id="Halogen.C3.A1cia_v_organickej_ch.C3.A9mii"></span>Halogenácia v organickej chémii</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen%C3%A1cia&amp;veaction=edit&amp;section=1" title="Upraviť sekciu: Halogenácia v organickej chémii" class="mw-editsection-visualeditor"><span>upraviť</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Halogen%C3%A1cia&amp;action=edit&amp;section=1" title="Editovat zdrojový kód sekce Halogenácia v organickej chémii"><span>upraviť zdroj</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Halogenácia môže prebiehať na nearomatických alebo aromatických zlúčeninách. </p> <div class="mw-heading mw-heading3"><h3 id="Aromatická_halogenácia"><span id="Aromatick.C3.A1_halogen.C3.A1cia"></span>Aromatická halogenácia</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen%C3%A1cia&amp;veaction=edit&amp;section=2" title="Upraviť sekciu: Aromatická halogenácia" class="mw-editsection-visualeditor"><span>upraviť</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Halogen%C3%A1cia&amp;action=edit&amp;section=2" title="Editovat zdrojový kód sekce Aromatická halogenácia"><span>upraviť zdroj</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ide o druh <a href="/wiki/Elektrofiln%C3%A1_aromatick%C3%A1_substit%C3%BAcia" title="Elektrofilná aromatická substitúcia">elektrofilnej aromatickej substitúcie</a>. </p> <div class="mw-heading mw-heading4"><h4 id="Fluorácia"><span id="Fluor.C3.A1cia"></span>Fluorácia</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen%C3%A1cia&amp;veaction=edit&amp;section=3" title="Upraviť sekciu: Fluorácia" class="mw-editsection-visualeditor"><span>upraviť</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Halogen%C3%A1cia&amp;action=edit&amp;section=3" title="Editovat zdrojový kód sekce Fluorácia"><span>upraviť zdroj</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Flu%C3%B3r" title="Fluór">Fluór</a> sa málokedy viaže na organické zlúčeniny. Je známych len približne 13 zlúčenín fluóru, ktoré sa vyskytujú v prírode.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Chlorácia"><span id="Chlor.C3.A1cia"></span>Chlorácia</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen%C3%A1cia&amp;veaction=edit&amp;section=4" title="Upraviť sekciu: Chlorácia" class="mw-editsection-visualeditor"><span>upraviť</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Halogen%C3%A1cia&amp;action=edit&amp;section=4" title="Editovat zdrojový kód sekce Chlorácia"><span>upraviť zdroj</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Samotný plynný <a href="/wiki/Chl%C3%B3r" title="Chlór">chlór</a> nereaguje s <a href="/wiki/Aromatick%C3%BD_uh%C4%BEovod%C3%ADk" class="mw-redirect" title="Aromatický uhľovodík">aromatickými systémami</a> pretože sú relatívne stabilné. Preto sa musí pridať katalyzátor, ktorý polarizuje molekulu chlóru. Najčastejšie sa ako katalyzátor používa <a href="/wiki/Chlorid_%C5%BEelezit%C3%BD" title="Chlorid železitý">FeCl<sub>3</sub></a>. </p> <dl><dd><span class="mw-default-size" typeof="mw:File"><a href="/wiki/S%C3%BAbor:Chloracia.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/2/2f/Chloracia.png" decoding="async" width="346" height="75" class="mw-file-element" data-file-width="346" data-file-height="75" /></a></span></dd></dl> <p>Aromatická chlorácia je <a href="/wiki/Elektrofiln%C3%A1_aromatick%C3%A1_substit%C3%BAcia" title="Elektrofilná aromatická substitúcia">elektrofilná substitúcia</a>, to znamená že bude mať príslušný mechanizmus. Katalyzátor <a href="/wiki/Chlorid_%C5%BEelezit%C3%BD" title="Chlorid železitý">FeCl<sub>3</sub></a> polarizuje molekulu <a href="/wiki/Chl%C3%B3r" title="Chlór">chlóru</a>, ktorá potom reaguje s benzénom. Takáto chlorácia benzénu prebieha s výťažkom 86%.<sup id="cite_ref-McMurry_9-0" class="reference"><a href="#cite_note-McMurry-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup><sup class="reference" style="white-space:nowrap;">:532</sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/S%C3%BAbor:Chloracia(mech).png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7f/Chloracia%28mech%29.png/220px-Chloracia%28mech%29.png" decoding="async" width="220" height="133" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7f/Chloracia%28mech%29.png/330px-Chloracia%28mech%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7f/Chloracia%28mech%29.png/440px-Chloracia%28mech%29.png 2x" data-file-width="509" data-file-height="307" /></a><figcaption>Mechanizmus chlorácie benzénu</figcaption></figure> <p>Aromatická chlorácia sa často využíva na prípravu činidla na <a href="/w/index.php?title=Friedel-Craftsofa_alkyl%C3%A1cia&amp;action=edit&amp;redlink=1" class="new" title="Friedel-Craftsofa alkylácia (stránka neexistuje)">alkyláciu</a> a <a href="/w/index.php?title=Friedel-Craftsofa_acyl%C3%A1cia&amp;action=edit&amp;redlink=1" class="new" title="Friedel-Craftsofa acylácia (stránka neexistuje)">acyláciu</a>. Taktiež sa využíva pri syntéze <a href="/wiki/Lie%C4%8Divo" title="Liečivo">liečiv</a> a <a href="/wiki/Prekurzor" title="Prekurzor">prekurzorov</a>. </p> <div class="mw-heading mw-heading4"><h4 id="Bromácia"><span id="Brom.C3.A1cia"></span>Bromácia</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen%C3%A1cia&amp;veaction=edit&amp;section=5" title="Upraviť sekciu: Bromácia" class="mw-editsection-visualeditor"><span>upraviť</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Halogen%C3%A1cia&amp;action=edit&amp;section=5" title="Editovat zdrojový kód sekce Bromácia"><span>upraviť zdroj</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Bromácia je analogická reakcia ku chlorácii. Na aromatický systém sa naväzuje <a href="/wiki/Br%C3%B3m" title="Bróm">bróm</a>. Ako katalyzátor sa často používa <a href="/w/index.php?title=Bromid_%C5%BEelezit%C3%BD&amp;action=edit&amp;redlink=1" class="new" title="Bromid železitý (stránka neexistuje)">FeBr<sub>3</sub></a>. Takáto bromácia prebieha s výťažkom približne 80%.<sup id="cite_ref-McMurry_9-1" class="reference"><a href="#cite_note-McMurry-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup><sup class="reference" style="white-space:nowrap;">:529</sup> </p><p>Mechanizmus aromatickej bromácie je úplne rovnaký ako mechanizmus chlorácie. Najprv <a href="/w/index.php?title=Bromid_%C5%BEelezit%C3%BD&amp;action=edit&amp;redlink=1" class="new" title="Bromid železitý (stránka neexistuje)">FeBr<sub>3</sub></a> polarizuje molekulu <a href="/wiki/Br%C3%B3m" title="Bróm">brómu</a> a tá následne reaguje s aromatickým systémom a uvoľňuje sa <a href="/wiki/Kyselina_bromovod%C3%ADkov%C3%A1" title="Kyselina bromovodíková">HBr</a>. </p> <dl><dd><span class="mw-default-size" typeof="mw:File"><a href="/wiki/S%C3%BAbor:Bromacia_benzenu.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/d/de/Bromacia_benzenu.png" decoding="async" width="334" height="75" class="mw-file-element" data-file-width="334" data-file-height="75" /></a></span></dd></dl> <p>Aromatická bromácia sa podobne ako chlorácia využíva na prípravu <a href="/wiki/Prekurzor" title="Prekurzor">prekurzorov</a> a <a href="/wiki/Lie%C4%8Divo" title="Liečivo">liečiv</a>. Používa sa však aj na prípravu veľmi populárneho <a href="/w/index.php?title=Grignardove_%C4%8Dinidlo&amp;action=edit&amp;redlink=1" class="new" title="Grignardove činidlo (stránka neexistuje)">Grignardovho činidla</a>. Toto <a href="/w/index.php?title=Organokovov%C3%A1_zl%C3%BA%C4%8Denina&amp;action=edit&amp;redlink=1" class="new" title="Organokovová zlúčenina (stránka neexistuje)">organokovové</a> činidlo slúži na predĺženie uhlíkového reťazca. </p> <div class="mw-heading mw-heading4"><h4 id="Jodácia"><span id="Jod.C3.A1cia"></span>Jodácia</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen%C3%A1cia&amp;veaction=edit&amp;section=6" title="Upraviť sekciu: Jodácia" class="mw-editsection-visualeditor"><span>upraviť</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Halogen%C3%A1cia&amp;action=edit&amp;section=6" title="Editovat zdrojový kód sekce Jodácia"><span>upraviť zdroj</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Jodácia je veľmi málo používaná reakcia. Samotný <a href="/wiki/J%C3%B3d" title="Jód">jód</a> nie je dostatočne reaktívny aby dokázal reagovať s pomerne stabilným aromatickým systémom. Preto sa ako katalyzátor pridáva <a href="/wiki/Oxidovadlo" class="mw-redirect" title="Oxidovadlo">oxidačné činidlo</a> ktoré zoxiduje <a href="/wiki/J%C3%B3d" title="Jód">jód</a> na <a href="/wiki/Elektrofil" title="Elektrofil">elektrofilnejšiu</a> zlúčeninu. Ako oxidovadlo sa používa <a href="/wiki/Peroxid_vod%C3%ADka" title="Peroxid vodíka">H<sub>2</sub>O<sub>2</sub></a>, <a href="/wiki/Kyselina_dusi%C4%8Dn%C3%A1" title="Kyselina dusičná">HNO<sub>3</sub></a> alebo nejaká <a href="/wiki/Me%C4%8F" title="Meď">meďnatá</a> soľ.<sup id="cite_ref-McMurry_9-2" class="reference"><a href="#cite_note-McMurry-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup><sup class="reference" style="white-space:nowrap;">:532</sup> </p> <dl><dd>I<sub>2</sub> + 2 Cu<sup>2+</sup> → 2 I<sup>+</sup> + 2 Cu<sup>+</sup></dd></dl> <p>Takto zoxidovaný katión <a href="/wiki/J%C3%B3d" title="Jód">jódu</a> potom reaguje s benzénom ako klasický <a href="/wiki/Elektrofil" title="Elektrofil">elektrofil</a>. </p> <dl><dd><span class="mw-default-size" typeof="mw:File"><a href="/wiki/S%C3%BAbor:Jodacia.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/b/b6/Jodacia.png" decoding="async" width="323" height="75" class="mw-file-element" data-file-width="323" data-file-height="75" /></a></span></dd></dl> <p>Výťažok takejto jodácie je okolo 65%. </p> <div class="mw-heading mw-heading2"><h2 id="Referencie">Referencie</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen%C3%A1cia&amp;veaction=edit&amp;section=7" title="Upraviť sekciu: Referencie" class="mw-editsection-visualeditor"><span>upraviť</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Halogen%C3%A1cia&amp;action=edit&amp;section=7" title="Editovat zdrojový kód sekce Referencie"><span>upraviť zdroj</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="references"><div class="mw-references-wrap"><ol class="references"> <li id="cite_note-:0-1"><span class="mw-cite-backlink">↑ <a href="#cite_ref-:0_1-0"><sup style="font-style: italic; font-weight: bold; vertical-align: top">a</sup></a> <a href="#cite_ref-:0_1-1"><sup style="font-style: italic; font-weight: bold; vertical-align: top">b</sup></a> <a href="#cite_ref-:0_1-2"><sup style="font-style: italic; font-weight: bold; vertical-align: top">c</sup></a> <a href="#cite_ref-:0_1-3"><sup style="font-style: italic; font-weight: bold; vertical-align: top">d</sup></a></span> <span class="reference-text"><cite style="font-style:normal">halogenácia.&#160;In:&#32;BÍNA, Jaroslav. <i><a href="/wiki/Mal%C3%A1_encyklop%C3%A9dia_ch%C3%A9mie" title="Malá encyklopédia chémie">Malá encyklopédia chémie</a></i>. 3. vyd. Bratislava&#160;: <a href="/wiki/Vydavate%C4%BEstvo_Obzor" title="Vydavateľstvo Obzor">Obzor</a>, 1981. 816&#160;s. (Malé encyklopédie vydavateľstva Obzor.) S.&#160;285. </cite></span> </li> <li id="cite_note-:1-2"><span class="mw-cite-backlink">↑ <a href="#cite_ref-:1_2-0"><sup style="font-style: italic; font-weight: bold; vertical-align: top">a</sup></a> <a href="#cite_ref-:1_2-1"><sup style="font-style: italic; font-weight: bold; vertical-align: top">b</sup></a></span> <span class="reference-text">halogenation. In: <cite style="font-style:normal"> <i>Article</i> [online]. accessscience.com, [cit. 2022-08-23]. <a rel="nofollow" class="external text" href="https://www.accessscience.com/content/halogenation/306700">Dostupné online.</a> </cite></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text"><cite style="font-style:normal">halogenace.&#160;In:&#32;KORBAŘ, Tomáš; STRÁNSKÝ, Antonín. <i>Technický naučný slovník</i>. 1. vyd. Zväzok 2 G&#160;&#8211;&#32;L. Praha&#160;: SNTL, 1962. 672&#160;s. (Řada technických slovníků.) S.&#160;55. </cite></span> </li> <li id="cite_note-:3-4"><span class="mw-cite-backlink">↑ <a href="#cite_ref-:3_4-0"><sup style="font-style: italic; font-weight: bold; vertical-align: top">a</sup></a> <a href="#cite_ref-:3_4-1"><sup style="font-style: italic; font-weight: bold; vertical-align: top">b</sup></a></span> <span class="reference-text"><cite style="font-style:normal">halogenácia.&#160;In:&#32; <i><a href="/wiki/Encyclopaedia_Beliana" title="Encyclopaedia Beliana">Encyclopaedia Beliana</a></i>. 1. vyd. Bratislava&#160;: <a href="/wiki/Encyklopedick%C3%BD_%C3%BAstav_Slovenskej_akad%C3%A9mie_vied" title="Encyklopedický ústav Slovenskej akadémie vied">Encyklopedický ústav SAV</a>; <a href="/wiki/VEDA,_vydavate%C4%BEstvo_Slovenskej_akad%C3%A9mie_vied" title="VEDA, vydavateľstvo Slovenskej akadémie vied">Veda</a>, 2008. 670&#160;s. <span style="white-space:nowrap"><a href="/wiki/%C5%A0peci%C3%A1lne:Kni%C5%BEn%C3%A9Zdroje/978-80-224-0982-7" title="Špeciálne:KnižnéZdroje/978-80-224-0982-7">ISBN <span class="&#73;SBN">978-80-224-0982-7</span></a></span>. Zväzok 5. (Galb – Hir), s.&#160;469. </cite></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text"><cite style="font-style:normal">halogenace.&#160;In:&#32; <i>Technický naučný slovník</i>. 1. vyd. Zväzok 2 G&#160;&#8211;&#32;L. Praha&#160;: SNTL, 1962. 672&#160;s. (Řada technických slovníků.) S.&#160;55. </cite></span> </li> <li id="cite_note-:2-6"><span class="mw-cite-backlink">↑ <a href="#cite_ref-:2_6-0"><sup style="font-style: italic; font-weight: bold; vertical-align: top">a</sup></a> <a href="#cite_ref-:2_6-1"><sup style="font-style: italic; font-weight: bold; vertical-align: top">b</sup></a> <a href="#cite_ref-:2_6-2"><sup style="font-style: italic; font-weight: bold; vertical-align: top">c</sup></a></span> <span class="reference-text"><cite style="font-style:normal">Halogenierung.&#160;In:&#32; <i>Lexikon der Chemie</i>. [CD-ROM] Heidelberg; Berlin&#160;: Spektrum, Akad. Verl., 2003. <span style="white-space:nowrap"><a href="/wiki/%C5%A0peci%C3%A1lne:Kni%C5%BEn%C3%A9Zdroje/978-3-8274-1151-8" title="Špeciálne:KnižnéZdroje/978-3-8274-1151-8">ISBN <span class="&#73;SBN">978-3-8274-1151-8</span></a></span>. </cite></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><a href="#cite_ref-7">↑</a></span> <span class="reference-text"><cite style="font-style:normal"> <i>halogenation</i> [online]. oxfordreference.com, [cit. 2022-08-23]. <a rel="nofollow" class="external text" href="https://www.oxfordreference.com/view/10.1093/oi/authority.20111010203638472">Dostupné online.</a> </cite></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><a href="#cite_ref-8">↑</a></span> <span class="reference-text"><cite style="font-style:normal">SU, Shun. <i>Fluorination of Organic Compounds</i>. [s.l.]&#160;: [s.n.]. <a rel="nofollow" class="external text" href="http://www.scripps.edu/baran/images/grpmtgpdf/Su_May_08.pdf">Dostupné online.</a> S.&#160;1. </cite></span> </li> <li id="cite_note-McMurry-9"><span class="mw-cite-backlink">↑ <a href="#cite_ref-McMurry_9-0"><sup style="font-style: italic; font-weight: bold; vertical-align: top">a</sup></a> <a href="#cite_ref-McMurry_9-1"><sup style="font-style: italic; font-weight: bold; vertical-align: top">b</sup></a> <a href="#cite_ref-McMurry_9-2"><sup style="font-style: italic; font-weight: bold; vertical-align: top">c</sup></a></span> <span class="reference-text"><cite style="font-style:normal">MCMURRY, John. <i>Organická chemie</i>. Preklad Jaroslav Jonas et al. Vyd. 1. V Brně; V Praze&#160;: Vysoké učení technické; Vysoká škola chemicko-technologická, 2007. 1176&#160;s. (Překlady vysokoškolských učebnic; zv. 2.) <span style="white-space:nowrap"><a href="/wiki/%C5%A0peci%C3%A1lne:Kni%C5%BEn%C3%A9Zdroje/978-80-214-3291-8" title="Špeciálne:KnižnéZdroje/978-80-214-3291-8">ISBN <span class="&#73;SBN">978-80-214-3291-8</span></a></span>, <span style="white-space:nowrap"><a href="/wiki/%C5%A0peci%C3%A1lne:Kni%C5%BEn%C3%A9Zdroje/978-80-7080-637-1" title="Špeciálne:KnižnéZdroje/978-80-7080-637-1"> <span class="&#73;SBN">978-80-7080-637-1</span></a></span>. </cite></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Pozri_aj">Pozri aj</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Halogen%C3%A1cia&amp;veaction=edit&amp;section=8" title="Upraviť sekciu: Pozri aj" class="mw-editsection-visualeditor"><span>upraviť</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Halogen%C3%A1cia&amp;action=edit&amp;section=8" title="Editovat zdrojový kód sekce Pozri aj"><span>upraviť zdroj</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Halog%C3%A9nderiv%C3%A1t" title="Halogénderivát">Halogénderivát</a></li></ul> <div style="border: solid #aaa 1px; background: #f9f9f9; padding: 0ex 1ex; font-size: 90%;" class="tright" title="Portál, ktorého súčasťou je táto stránka"> <table style="margin: 0; padding: 0ex"> <tbody><tr> <td style="vertical-align:middle;margin: 0;"><span class="noviewer" typeof="mw:File"><a href="/wiki/S%C3%BAbor:Portal.svg" class="mw-file-description" title="Portal"><img alt="Portal" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Portal.svg/36px-Portal.svg.png" decoding="async" width="36" height="32" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Portal.svg/54px-Portal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Portal.svg/72px-Portal.svg.png 2x" data-file-width="36" data-file-height="32" /></a></span> </td> <td style="text-align:left;font-style:italic; font-weight:bold;"><a href="/wiki/Port%C3%A1l:Ch%C3%A9mia" title="Portál:Chémia">Chemický portál</a> </td></tr></tbody></table></div> <!-- NewPP limit report Parsed by mw‐web.codfw.main‐f69cdc8f6‐s7r2r Cached time: 20241123193412 Cache expiry: 2592000 Reduced expiry: false Complications: [show‐toc] CPU time usage: 0.110 seconds Real time usage: 0.146 seconds Preprocessor visited node count: 2229/1000000 Post‐expand include size: 10255/2097152 bytes Template argument size: 3187/2097152 bytes Highest expansion depth: 12/100 Expensive parser function count: 1/500 Unstrip recursion depth: 0/20 Unstrip post‐expand size: 8829/5000000 bytes Lua time usage: 0.004/10.000 seconds Lua memory usage: 630722/52428800 bytes Number of Wikibase entities loaded: 0/400 --> <!-- Transclusion expansion time report (%,ms,calls,template) 100.00% 81.522 1 -total 83.86% 68.363 1 Šablóna:Referencie 50.24% 40.954 7 Šablóna:Citácia_knihy 28.45% 23.193 1 Šablóna:Beliana 25.49% 20.781 4 Šablóna:ISBN 9.34% 7.617 1 Šablóna:Portál 8.62% 7.031 2 Šablóna:Citácia_elektronického_dokumentu 7.10% 5.788 1 Šablóna:Cite_book 4.73% 3.855 3 Šablóna:Rp 4.12% 3.361 1 Šablóna:Portál/Riadok --> <!-- Saved in parser cache with key skwiki:pcache:idhash:434499-0!canonical and timestamp 20241123193412 and revision id 7781371. 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