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Alchini - Wikipedia

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mw-list-item user-links-collapsible-item"><a data-mw="interface" href="//donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&amp;utm_medium=sidebar&amp;utm_campaign=C13_it.wikipedia.org&amp;uselang=it" class=""><span>Fai una donazione</span></a> </li> <li id="pt-createaccount-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Speciale:CreaUtenza&amp;returnto=Alchini" title="Si consiglia di registrarsi e di effettuare l&#039;accesso, anche se non è obbligatorio" class=""><span>registrati</span></a> </li> <li id="pt-login-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Speciale:Entra&amp;returnto=Alchini" title="Si consiglia di effettuare l&#039;accesso, anche se non è obbligatorio [o]" accesskey="o" class=""><span>entra</span></a> </li> </ul> </div> </div> </div> <div id="vector-user-links-dropdown" 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class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">nascondi</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">Inizio</div> </a> </li> <li id="toc-Nomenclatura_IUPAC" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Nomenclatura_IUPAC"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Nomenclatura IUPAC</span> </div> </a> <ul id="toc-Nomenclatura_IUPAC-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fonti_industriali" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Fonti_industriali"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Fonti industriali</span> </div> </a> <ul id="toc-Fonti_industriali-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Preparazioni_per_sintesi" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Preparazioni_per_sintesi"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Preparazioni per sintesi</span> </div> </a> <ul id="toc-Preparazioni_per_sintesi-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reazioni_tipiche" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reazioni_tipiche"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Reazioni tipiche</span> </div> </a> <ul id="toc-Reazioni_tipiche-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Note" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Note"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Note</span> </div> </a> <ul id="toc-Note-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bibliografia" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Bibliografia"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Bibliografia</span> </div> </a> <ul id="toc-Bibliografia-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Voci_correlate" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Voci_correlate"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Voci correlate</span> </div> </a> <ul id="toc-Voci_correlate-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Altri_progetti" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Altri_progetti"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Altri progetti</span> </div> </a> <ul id="toc-Altri_progetti-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Collegamenti_esterni" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Collegamenti_esterni"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Collegamenti esterni</span> </div> </a> <ul id="toc-Collegamenti_esterni-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="Indice" 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="Mostra/Nascondi l&#039;indice" > <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">Mostra/Nascondi l&#039;indice</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">Alchini</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="Vai a una voce in un&#039;altra lingua. Disponibile in 80 lingue" > <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-80" 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">80 lingue</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Alkyn" title="Alkyn - afrikaans" lang="af" hreflang="af" data-title="Alkyn" data-language-autonym="Afrikaans" data-language-local-name="afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D9%84%D9%83%D8%A7%D9%8A%D9%86" title="ألكاين - arabo" lang="ar" hreflang="ar" data-title="ألكاين" data-language-autonym="العربية" data-language-local-name="arabo" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Alqu%C3%ADn" title="Alquín - asturiano" lang="ast" hreflang="ast" data-title="Alquín" data-language-autonym="Asturianu" data-language-local-name="asturiano" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Alkinl%C9%99r" title="Alkinlər - azerbaigiano" lang="az" hreflang="az" data-title="Alkinlər" data-language-autonym="Azərbaycanca" data-language-local-name="azerbaigiano" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Alkino" title="Alkino - Central Bikol" lang="bcl" hreflang="bcl" data-title="Alkino" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target"><span>Bikol Central</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D1%96%D0%BD%D1%8B" title="Алкіны - bielorusso" lang="be" hreflang="be" data-title="Алкіны" data-language-autonym="Беларуская" data-language-local-name="bielorusso" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%90%D0%BB%D1%8C%D0%BA%D1%96%D0%BD%D1%8B" title="Алькіны - Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Алькіны" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B8%D0%BD" title="Алкин - bulgaro" lang="bg" hreflang="bg" data-title="Алкин" data-language-autonym="Български" data-language-local-name="bulgaro" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%85%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B2%E0%A6%95%E0%A6%BE%E0%A6%87%E0%A6%A8" title="অ্যালকাইন - bengalese" lang="bn" hreflang="bn" data-title="অ্যালকাইন" data-language-autonym="বাংলা" data-language-local-name="bengalese" 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/Alkini" title="Alkini - bosniaco" lang="bs" hreflang="bs" data-title="Alkini" data-language-autonym="Bosanski" data-language-local-name="bosniaco" 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/Alqu%C3%AD" title="Alquí - catalano" lang="ca" hreflang="ca" data-title="Alquí" data-language-autonym="Català" data-language-local-name="catalano" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%A6%DB%95%D9%84%DA%A9%D8%A7%DB%8C%D9%86" title="ئەلکاین - curdo centrale" lang="ckb" hreflang="ckb" data-title="ئەلکاین" data-language-autonym="کوردی" data-language-local-name="curdo centrale" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Alkyny" title="Alkyny - ceco" lang="cs" hreflang="cs" data-title="Alkyny" data-language-autonym="Čeština" data-language-local-name="ceco" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Alcyn" title="Alcyn - gallese" lang="cy" hreflang="cy" data-title="Alcyn" data-language-autonym="Cymraeg" data-language-local-name="gallese" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Alkyn" title="Alkyn - danese" lang="da" hreflang="da" data-title="Alkyn" data-language-autonym="Dansk" data-language-local-name="danese" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de badge-Q17437796 badge-featuredarticle mw-list-item" title="voce in vetrina"><a href="https://de.wikipedia.org/wiki/Alkine" title="Alkine - tedesco" lang="de" hreflang="de" data-title="Alkine" data-language-autonym="Deutsch" data-language-local-name="tedesco" 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%91%CE%BB%CE%BA%CE%AF%CE%BD%CE%B9%CE%B1" title="Αλκίνια - greco" lang="el" hreflang="el" data-title="Αλκίνια" data-language-autonym="Ελληνικά" data-language-local-name="greco" 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/Alkyne" title="Alkyne - inglese" lang="en" hreflang="en" data-title="Alkyne" data-language-autonym="English" data-language-local-name="inglese" 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/Alkino" title="Alkino - esperanto" lang="eo" hreflang="eo" data-title="Alkino" 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/Alquino" title="Alquino - spagnolo" lang="es" hreflang="es" data-title="Alquino" data-language-autonym="Español" data-language-local-name="spagnolo" 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/Alk%C3%BC%C3%BCnid" title="Alküünid - estone" lang="et" hreflang="et" data-title="Alküünid" data-language-autonym="Eesti" data-language-local-name="estone" 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/Alkino" title="Alkino - basco" lang="eu" hreflang="eu" data-title="Alkino" data-language-autonym="Euskara" data-language-local-name="basco" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A2%D9%84%DA%A9%DB%8C%D9%86" title="آلکین - persiano" lang="fa" hreflang="fa" data-title="آلکین" data-language-autonym="فارسی" data-language-local-name="persiano" 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/Alkyynit" title="Alkyynit - finlandese" lang="fi" hreflang="fi" data-title="Alkyynit" data-language-autonym="Suomi" data-language-local-name="finlandese" 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/Alcyne" title="Alcyne - francese" lang="fr" hreflang="fr" data-title="Alcyne" data-language-autonym="Français" data-language-local-name="francese" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Ailc%C3%ADn" title="Ailcín - irlandese" lang="ga" hreflang="ga" data-title="Ailcín" data-language-autonym="Gaeilge" data-language-local-name="irlandese" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Alquino" title="Alquino - galiziano" lang="gl" hreflang="gl" data-title="Alquino" data-language-autonym="Galego" data-language-local-name="galiziano" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%9C%D7%A7%D7%99%D7%9F" title="אלקין - ebraico" lang="he" hreflang="he" data-title="אלקין" data-language-autonym="עברית" data-language-local-name="ebraico" 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%90%E0%A4%B2%E0%A5%8D%E0%A4%95%E0%A4%BE%E0%A4%87%E0%A4%A8" title="ऐल्काइन - hindi" lang="hi" hreflang="hi" data-title="ऐल्काइन" data-language-autonym="हिन्दी" data-language-local-name="hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Alkini" title="Alkini - croato" lang="hr" hreflang="hr" data-title="Alkini" data-language-autonym="Hrvatski" data-language-local-name="croato" 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/Alkinek" title="Alkinek - ungherese" lang="hu" hreflang="hu" data-title="Alkinek" data-language-autonym="Magyar" data-language-local-name="ungherese" 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/%D4%B1%D5%AC%D5%AF%D5%AB%D5%B6%D5%B6%D5%A5%D6%80" title="Ալկիններ - armeno" lang="hy" hreflang="hy" data-title="Ալկիններ" data-language-autonym="Հայերեն" data-language-local-name="armeno" 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/Alkuna" title="Alkuna - indonesiano" lang="id" hreflang="id" data-title="Alkuna" data-language-autonym="Bahasa Indonesia" data-language-local-name="indonesiano" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%83%AB%E3%82%AD%E3%83%B3" title="アルキン - giapponese" lang="ja" hreflang="ja" data-title="アルキン" data-language-autonym="日本語" data-language-local-name="giapponese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Alkuna" title="Alkuna - giavanese" lang="jv" hreflang="jv" data-title="Alkuna" data-language-autonym="Jawa" data-language-local-name="giavanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%90%E1%83%9A%E1%83%99%E1%83%98%E1%83%9C%E1%83%98" title="ალკინი - georgiano" lang="ka" hreflang="ka" data-title="ალკინი" data-language-autonym="ქართული" data-language-local-name="georgiano" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B8%D0%BD%D0%B4%D0%B5%D1%80" title="Алкиндер - kazako" lang="kk" hreflang="kk" data-title="Алкиндер" data-language-autonym="Қазақша" data-language-local-name="kazako" 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/%EC%95%8C%EC%B9%B4%EC%9D%B8" title="알카인 - coreano" lang="ko" hreflang="ko" data-title="알카인" data-language-autonym="한국어" data-language-local-name="coreano" 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%90%D0%BB%D0%BA%D0%B8%D0%BD%D0%B4%D0%B5%D1%80" title="Алкиндер - kirghiso" lang="ky" hreflang="ky" data-title="Алкиндер" data-language-autonym="Кыргызча" data-language-local-name="kirghiso" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Alkinum" title="Alkinum - latino" lang="la" hreflang="la" data-title="Alkinum" data-language-autonym="Latina" data-language-local-name="latino" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Alchin" title="Alchin - lombardo" lang="lmo" hreflang="lmo" data-title="Alchin" data-language-autonym="Lombard" data-language-local-name="lombardo" class="interlanguage-link-target"><span>Lombard</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Acetileniniai_angliavandeniliai" title="Acetileniniai angliavandeniliai - lituano" lang="lt" hreflang="lt" data-title="Acetileniniai angliavandeniliai" data-language-autonym="Lietuvių" data-language-local-name="lituano" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Alk%C4%ABni" title="Alkīni - lettone" lang="lv" hreflang="lv" data-title="Alkīni" data-language-autonym="Latviešu" data-language-local-name="lettone" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B8%D0%BD" title="Алкин - macedone" lang="mk" hreflang="mk" data-title="Алкин" data-language-autonym="Македонски" data-language-local-name="macedone" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%86%E0%B5%BD%E0%B4%95%E0%B5%8D%E0%B4%95%E0%B5%88%E0%B5%BB" title="ആൽക്കൈൻ - malayalam" lang="ml" hreflang="ml" data-title="ആൽക്കൈൻ" data-language-autonym="മലയാളം" data-language-local-name="malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Alkuna" title="Alkuna - malese" lang="ms" hreflang="ms" data-title="Alkuna" data-language-autonym="Bahasa Melayu" data-language-local-name="malese" 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/Alkyn" title="Alkyn - olandese" lang="nl" hreflang="nl" data-title="Alkyn" data-language-autonym="Nederlands" data-language-local-name="olandese" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Alkyn" title="Alkyn - norvegese nynorsk" lang="nn" hreflang="nn" data-title="Alkyn" data-language-autonym="Norsk nynorsk" data-language-local-name="norvegese nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Alkyner" title="Alkyner - norvegese bokmål" lang="nb" hreflang="nb" data-title="Alkyner" data-language-autonym="Norsk bokmål" data-language-local-name="norvegese bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-om mw-list-item"><a href="https://om.wikipedia.org/wiki/Alkaayinii" title="Alkaayinii - oromo" lang="om" hreflang="om" data-title="Alkaayinii" data-language-autonym="Oromoo" data-language-local-name="oromo" class="interlanguage-link-target"><span>Oromoo</span></a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%85%E0%A8%B2%E0%A8%95%E0%A8%BE%E0%A8%88%E0%A8%A8" title="ਅਲਕਾਈਨ - punjabi" lang="pa" hreflang="pa" data-title="ਅਲਕਾਈਨ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Alkiny" title="Alkiny - polacco" lang="pl" hreflang="pl" data-title="Alkiny" data-language-autonym="Polski" data-language-local-name="polacco" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-ps mw-list-item"><a href="https://ps.wikipedia.org/wiki/%D8%A7%D9%84%DA%A9%D8%A7%D9%8A%D9%86" title="الکاين - pashto" lang="ps" hreflang="ps" data-title="الکاين" data-language-autonym="پښتو" data-language-local-name="pashto" class="interlanguage-link-target"><span>پښتو</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Alcino" title="Alcino - portoghese" lang="pt" hreflang="pt" data-title="Alcino" data-language-autonym="Português" data-language-local-name="portoghese" 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/Alchin%C4%83" title="Alchină - rumeno" lang="ro" hreflang="ro" data-title="Alchină" data-language-autonym="Română" data-language-local-name="rumeno" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru badge-Q17437798 badge-goodarticle mw-list-item" title="voce di qualità"><a href="https://ru.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B8%D0%BD%D1%8B" title="Алкины - russo" lang="ru" hreflang="ru" data-title="Алкины" data-language-autonym="Русский" data-language-local-name="russo" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-rue mw-list-item"><a href="https://rue.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B8%D0%BD%D1%8B" title="Алкины - ruteno" lang="rue" hreflang="rue" data-title="Алкины" data-language-autonym="Русиньскый" data-language-local-name="ruteno" class="interlanguage-link-target"><span>Русиньскый</span></a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Alkyne" title="Alkyne - scozzese" lang="sco" hreflang="sco" data-title="Alkyne" data-language-autonym="Scots" data-language-local-name="scozzese" class="interlanguage-link-target"><span>Scots</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Alkin" title="Alkin - serbo-croato" lang="sh" hreflang="sh" data-title="Alkin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="serbo-croato" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-si mw-list-item"><a href="https://si.wikipedia.org/wiki/%E0%B6%87%E0%B6%BD%E0%B7%8A%E0%B6%9A%E0%B6%BA%E0%B7%92%E0%B6%B1" title="ඇල්කයින - singalese" lang="si" hreflang="si" data-title="ඇල්කයින" data-language-autonym="සිංහල" data-language-local-name="singalese" class="interlanguage-link-target"><span>සිංහල</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Alkyne" title="Alkyne - Simple English" lang="en-simple" hreflang="en-simple" data-title="Alkyne" 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/Alk%C3%ADn" title="Alkín - slovacco" lang="sk" hreflang="sk" data-title="Alkín" data-language-autonym="Slovenčina" data-language-local-name="slovacco" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Alkin" title="Alkin - sloveno" lang="sl" hreflang="sl" data-title="Alkin" data-language-autonym="Slovenščina" data-language-local-name="sloveno" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Alkinet" title="Alkinet - albanese" lang="sq" hreflang="sq" data-title="Alkinet" data-language-autonym="Shqip" data-language-local-name="albanese" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B8%D0%BD" title="Алкин - serbo" lang="sr" hreflang="sr" data-title="Алкин" data-language-autonym="Српски / srpski" data-language-local-name="serbo" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Alkuna" title="Alkuna - sundanese" lang="su" hreflang="su" data-title="Alkuna" data-language-autonym="Sunda" data-language-local-name="sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Alkyn" title="Alkyn - svedese" lang="sv" hreflang="sv" data-title="Alkyn" data-language-autonym="Svenska" data-language-local-name="svedese" 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%AF%8D%E0%AE%95%E0%AF%8D%E0%AE%95%E0%AF%88%E0%AE%A9%E0%AF%8D" title="ஆல்க்கைன் - tamil" lang="ta" hreflang="ta" data-title="ஆல்க்கைன்" data-language-autonym="தமிழ்" data-language-local-name="tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%81%E0%B8%AD%E0%B8%A5%E0%B9%84%E0%B8%84%E0%B8%99%E0%B9%8C" title="แอลไคน์ - thailandese" lang="th" hreflang="th" data-title="แอลไคน์" data-language-autonym="ไทย" data-language-local-name="thailandese" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Alkin" title="Alkin - turco" lang="tr" hreflang="tr" data-title="Alkin" data-language-autonym="Türkçe" data-language-local-name="turco" 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/Alkinnar" title="Alkinnar - tataro" lang="tt" hreflang="tt" data-title="Alkinnar" data-language-autonym="Татарча / tatarça" data-language-local-name="tataro" 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%90%D0%BB%D0%BA%D1%96%D0%BD%D0%B8" title="Алкіни - ucraino" lang="uk" hreflang="uk" data-title="Алкіни" data-language-autonym="Українська" data-language-local-name="ucraino" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%A7%D9%84%DA%A9%D8%A7%D8%A6%DB%8C%D9%86" title="الکائین - urdu" lang="ur" hreflang="ur" data-title="الکائین" data-language-autonym="اردو" data-language-local-name="urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-uz badge-Q17437798 badge-goodarticle mw-list-item" title="voce di qualità"><a href="https://uz.wikipedia.org/wiki/Alkinlar" title="Alkinlar - uzbeco" lang="uz" hreflang="uz" data-title="Alkinlar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="uzbeco" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Alkyn" title="Alkyn - vietnamita" lang="vi" hreflang="vi" data-title="Alkyn" data-language-autonym="Tiếng Việt" data-language-local-name="vietnamita" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Alkino" title="Alkino - waray" lang="war" hreflang="war" data-title="Alkino" data-language-autonym="Winaray" data-language-local-name="waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E7%82%94%E7%83%83" title="炔烃 - wu" lang="wuu" hreflang="wuu" data-title="炔烃" data-language-autonym="吴语" data-language-local-name="wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%82%94%E7%83%83" title="炔烃 - cinese" lang="zh" hreflang="zh" data-title="炔烃" data-language-autonym="中文" data-language-local-name="cinese" class="interlanguage-link-target"><span>中文</span></a></li><li class="interlanguage-link interwiki-zh-classical mw-list-item"><a href="https://zh-classical.wikipedia.org/wiki/%E7%82%94%E7%83%B4" title="炔烴 - cinese classico" lang="lzh" hreflang="lzh" data-title="炔烴" data-language-autonym="文言" data-language-local-name="cinese classico" class="interlanguage-link-target"><span>文言</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E7%82%94%E7%83%B4" title="炔烴 - cantonese" lang="yue" hreflang="yue" data-title="炔烴" data-language-autonym="粵語" data-language-local-name="cantonese" class="interlanguage-link-target"><span>粵語</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q159226#sitelinks-wikipedia" title="Modifica collegamenti interlinguistici" class="wbc-editpage">Modifica collegamenti</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespace"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Alchini" title="Vedi la voce [c]" accesskey="c"><span>Voce</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Discussione:Alchini" rel="discussion" title="Vedi le discussioni relative a questa pagina [t]" accesskey="t"><span>Discussione</span></a></li> </ul> </div> </div> <div id="vector-variants-dropdown" class="vector-dropdown emptyPortlet" > <input type="checkbox" id="vector-variants-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-variants-dropdown" class="vector-dropdown-checkbox " aria-label="Cambia versione linguistica" > <label id="vector-variants-dropdown-label" for="vector-variants-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">italiano</span> </label> <div class="vector-dropdown-content"> <div 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class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Alchini&amp;action=history" title="Versioni precedenti di questa pagina [h]" accesskey="h"><span>Cronologia</span></a></li> </ul> </div> </div> </nav> <nav class="vector-page-tools-landmark" aria-label="Strumenti pagine"> <div id="vector-page-tools-dropdown" class="vector-dropdown vector-page-tools-dropdown" > <input type="checkbox" id="vector-page-tools-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-tools-dropdown" class="vector-dropdown-checkbox " aria-label="Strumenti" > <label id="vector-page-tools-dropdown-label" for="vector-page-tools-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">Strumenti</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-tools-unpinned-container" class="vector-unpinned-container"> <div id="vector-page-tools" class="vector-page-tools vector-pinnable-element"> <div class="vector-pinnable-header vector-page-tools-pinnable-header vector-pinnable-header-unpinned" data-feature-name="page-tools-pinned" data-pinnable-element-id="vector-page-tools" data-pinned-container-id="vector-page-tools-pinned-container" data-unpinned-container-id="vector-page-tools-unpinned-container" > <div class="vector-pinnable-header-label">Strumenti</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-page-tools.pin">sposta nella barra laterale</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-page-tools.unpin">nascondi</button> </div> <div id="p-cactions" class="vector-menu mw-portlet mw-portlet-cactions emptyPortlet vector-has-collapsible-items" title="Altre opzioni" > <div 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lang="it" dir="ltr"><p>Gli <b>alchini</b> sono <a href="/wiki/Composto_organico" title="Composto organico">composti</a> <a href="/wiki/Chimica_organica" title="Chimica organica">organici</a> a catena aperta costituiti solamente da <a href="/wiki/Atomo" title="Atomo">atomi</a> di <a href="/wiki/Carbonio" title="Carbonio">carbonio</a> e di <a href="/wiki/Idrogeno" title="Idrogeno">idrogeno</a> (e per questo appartenenti alla più ampia classe degli <a href="/wiki/Idrocarburi" title="Idrocarburi">idrocarburi</a>) aventi formula bruta C<sub>n</sub>H<sub>(2n - 2)</sub>. </p><p>Come nel caso degli <a href="/wiki/Alcani" title="Alcani">alcani</a>, gli atomi di carbonio sono uniti tra loro attraverso <a href="/wiki/Legame_covalente" title="Legame covalente">legami covalenti</a> a formare una catena aperta, lineare o ramificata, due atomi carbonio adiacenti sono però uniti da un legame covalente triplo.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Alkyne_General_Formulae_V.1.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6a/Alkyne_General_Formulae_V.1.png/220px-Alkyne_General_Formulae_V.1.png" decoding="async" width="220" height="232" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6a/Alkyne_General_Formulae_V.1.png/330px-Alkyne_General_Formulae_V.1.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6a/Alkyne_General_Formulae_V.1.png/440px-Alkyne_General_Formulae_V.1.png 2x" data-file-width="978" data-file-height="1032" /></a><figcaption>Alcuni esempi di alchini</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Acetylene-CRC-IR-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Acetylene-CRC-IR-3D-balls.png/220px-Acetylene-CRC-IR-3D-balls.png" decoding="async" width="220" height="64" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Acetylene-CRC-IR-3D-balls.png/330px-Acetylene-CRC-IR-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Acetylene-CRC-IR-3D-balls.png/440px-Acetylene-CRC-IR-3D-balls.png 2x" data-file-width="1100" data-file-height="318" /></a><figcaption>Rappresentazione della molecola dell'<a href="/wiki/Acetilene" title="Acetilene">acetilene</a></figcaption></figure> <p>L'alchino con la più bassa <a href="/wiki/Massa_molecolare" title="Massa molecolare">massa molecolare</a> è l'etino (comunemente detto <a href="/wiki/Acetilene" title="Acetilene">acetilene</a>), avente formula HC≡CH. Per questo motivo questa serie di idrocarburi viene chiamata anche <b>serie acetilenica</b>. </p><p>I due atomi di carbonio coinvolti nel triplo legame presentano <a href="/wiki/Orbitale_atomico" title="Orbitale atomico">orbitali</a> <a href="/wiki/Ibridizzazione" title="Ibridizzazione">ibridi</a> di tipo <i>sp</i>, questo fa sì che i due atomi uniti dal triplo legame e i due atomi loro immediatamente legati siano tra loro allineati. </p><p>Un legame C-C è di tipo <b><a href="/wiki/Legame_%CF%83" title="Legame σ">σ</a></b>, formato dalla sovrapposizione di due orbitali ibridi <i>sp</i> lungo l'asse del legame; il secondo ed il terzo legame sono di tipo <b><a href="/wiki/Legame_%CF%80" title="Legame π">π</a></b>, formati dalla sovrapposizione in direzione perpendicolare all'asse del legame delle due coppie di orbitali <i>p</i> non coinvolte nell'ibridazione. Tale doppia sovrapposizione va a formare un unico orbitale approssimativamente a forma di tubo che avvolge l'asse del legame C-C lungo la sua lunghezza. </p><p>Particolarità chimica degli alchini è l'acidità degli idrogeni legati ai carboni coinvolti nel triplo legame. Tale acidità permette la formazione di sali, chiamati "carburi". Il più comune di questi è il <a href="/wiki/Carburo_di_calcio" title="Carburo di calcio">carburo di calcio</a> (CaC<sub>2</sub>), usato dagli speleologi per produrre acetilene <i>in situ</i> da bruciare nelle apposite lampade per produrre luce. </p><p>L'anione dell'acetilene HC≡C<sup>-</sup> viene chiamato <i>acetiluro</i>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Nomenclatura_IUPAC">Nomenclatura IUPAC</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alchini&amp;veaction=edit&amp;section=1" title="Modifica la sezione Nomenclatura IUPAC" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alchini&amp;action=edit&amp;section=1" title="Edit section&#039;s source code: Nomenclatura IUPAC"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>La nomenclatura <a href="/wiki/Unione_internazionale_di_chimica_pura_e_applicata" title="Unione internazionale di chimica pura e applicata">IUPAC</a> degli <b>alchini</b> segue regole simili a quella degli <a href="/wiki/Alcani" title="Alcani">alcani</a>, tuttavia occorre evidenziare alcune differenze: </p> <ul><li>quando si individua la catena principale della molecola, questa deve includere i due atomi di carbonio coinvolti nel triplo legame.</li> <li>il nome che viene dato alla catena principale è simile a quanto previsto per gli alcani, ma il suffisso <i>-ano</i> viene sostituito dal suffisso <i>-ino</i> (<a href="/wiki/Etino" class="mw-redirect" title="Etino">etino</a>, <a href="/wiki/Propino" title="Propino">propino</a>, <a href="/wiki/1-butino" class="mw-redirect" title="1-butino">butino</a>, <a href="/wiki/Pentino" title="Pentino">pentino</a>, <a href="/wiki/Esino_(chimica)" title="Esino (chimica)">esino</a>, <a href="/w/index.php?title=Eptino&amp;action=edit&amp;redlink=1" class="new" title="Eptino (la pagina non esiste)">eptino</a>, <a href="/wiki/Ottino" title="Ottino">ottino</a>, etc...)</li> <li>nel numerare la catena principale, il numero più basso possibile dovrà essere assegnato ai due atomi di carbonio coinvolti nel triplo legame.</li> <li>nel caso il composto contenga sia un doppio che un triplo legame si usa il suffisso <i>-enino</i> e la numerazione di questa catena inizia dall'estremità più prossima ad un legame multiplo (doppio o triplo che sia), ma nel caso di posizioni equivalenti si assegna il numero inferiore al doppio legame.</li></ul> <div class="mw-heading mw-heading2"><h2 id="Fonti_industriali">Fonti industriali</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alchini&amp;veaction=edit&amp;section=2" title="Modifica la sezione Fonti industriali" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alchini&amp;action=edit&amp;section=2" title="Edit section&#039;s source code: Fonti industriali"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>L'unico alchino di interesse industriale è l'<a href="/wiki/Etino" class="mw-redirect" title="Etino">etino</a>, o <i>acetilene</i>. In passato veniva prodotto per <a href="/wiki/Idrolisi" title="Idrolisi">idrolisi</a> del carburo di calcio, a sua volta ottenuto per riscaldamento di carbon <a href="/wiki/Coke_(carbone)" class="mw-redirect" title="Coke (carbone)">coke</a> e <a href="/wiki/Ossido_di_calcio" title="Ossido di calcio">ossido di calcio</a> </p> <pre>CaO + 3 C → CaC<sub>2</sub> + CO<br /> CaC<sub>2</sub> + 2 H<sub>2</sub>O → HC≡CH + Ca(OH)<sub>2</sub> </pre> <p>Mentre ora si ricorre preferenzialmente alla <a href="/wiki/Pirolisi" title="Pirolisi">pirolisi</a> del metano a 1500&#160;°C in condizioni controllate </p> <pre>2 CH<sub>4</sub> → HC≡CH + 3 H<sub>2</sub> </pre> <p>L'acetilene è instabile e quindi molto pericoloso da stoccare e maneggiare. Stoccato in bombola, viene stabilizzato aggiungendovi pezzi di pietra pomice saturi di <a href="/wiki/Acetone" title="Acetone">acetone</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Preparazioni_per_sintesi">Preparazioni per sintesi</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alchini&amp;veaction=edit&amp;section=3" title="Modifica la sezione Preparazioni per sintesi" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alchini&amp;action=edit&amp;section=3" title="Edit section&#039;s source code: Preparazioni per sintesi"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><b>deidroalogenazione di di<a href="/wiki/Alogenuri_alchilici" title="Alogenuri alchilici">alogenuri alchilici</a></b> geminali o vicinali</li></ul> <pre>R-CX<sub>2</sub>-CH<sub>2</sub>-R' + KOH fusa → R-C≡C-R'<br /> R-CHX-CHX-R' + KOH fusa → R-C≡C-R' </pre> <p>la rimozione di due molecole di HX richiede condizioni piuttosto drastiche (trattamento con <a href="/wiki/Potassio_idrato" class="mw-redirect" title="Potassio idrato">potassio idrato</a> fuso o soluzioni molto concentrate di potassio idrato in <a href="/wiki/Etanolo" title="Etanolo">etanolo</a> a caldo) nelle quali il triplo legame può migrare all'interno della catena formando alchini disostituiti, più stabili. </p><p>Una base sufficientemente forte da consentire la reazione senza provocare la migrazione del triplo legame è la <a href="/wiki/Sodioammide" class="mw-redirect" title="Sodioammide">sodioammide</a>, prodotto della reazione tra <a href="/wiki/Sodio" title="Sodio">sodio</a> metallico e <a href="/wiki/Ammoniaca" title="Ammoniaca">ammoniaca</a> </p> <pre>R-CX<sub>2</sub>-CH<sub>3</sub> + NaNH<sub>2</sub> → R-C≡CH<br /> R-CHX-CH<sub>2</sub>X + NaNH<sub>2</sub> → R-C≡CH </pre> <ul><li><b>sostituzione nucleofila</b> tra un acetiluro ed un alogenuro alchilico</li></ul> <pre>H-C≡C<sup>-</sup> + R-X → H-C≡C-R + X<sup>-</sup><br /> R-C≡C<sup>-</sup> + R'-X → R-C≡C-R' + X<sup>-</sup> </pre> <dl><dd>permette di preparare alchini sostituiti partendo dall'acetilene. Lo ione acetiluro, preparato per reazione tra l'alchino ed una base forte (in genere sodioammide o butil-<a href="/wiki/Litio" title="Litio">litio</a>) si va a sostituire all'atomo di alogeno dell'alogenuro alchilico.</dd></dl> <div class="mw-heading mw-heading2"><h2 id="Reazioni_tipiche">Reazioni tipiche</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alchini&amp;veaction=edit&amp;section=4" title="Modifica la sezione Reazioni tipiche" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alchini&amp;action=edit&amp;section=4" title="Edit section&#039;s source code: Reazioni tipiche"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Come per gli <a href="/wiki/Alcheni" title="Alcheni">alcheni</a>, anche la maggior parte della reattività degli alchini si esplica attraverso <a href="/wiki/Reazione_di_addizione" title="Reazione di addizione">reazioni di addizione</a> al triplo legame. Le reazioni di addizione possono essere lasciate procedere fino all'ottenimento di composti <i>saturi</i> (cioè con atomi legati tra loro solo da legami semplici) oppure essere condotte in condizioni tali da favorire un'addizione parziale, trasformando quindi il triplo legame in un legame doppio. </p> <ul><li><b>addizione di idrogeno</b> (formazione di <a href="/wiki/Alcani" title="Alcani">alcani</a> e di <a href="/wiki/Alcheni" title="Alcheni">alcheni</a>)</li></ul> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Hydrogenation_Heterogenic_V.1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Hydrogenation_Heterogenic_V.1.svg/310px-Hydrogenation_Heterogenic_V.1.svg.png" decoding="async" width="310" height="103" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Hydrogenation_Heterogenic_V.1.svg/465px-Hydrogenation_Heterogenic_V.1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Hydrogenation_Heterogenic_V.1.svg/620px-Hydrogenation_Heterogenic_V.1.svg.png 2x" data-file-width="619" data-file-height="206" /></a><figcaption>Addizione di idrogeno</figcaption></figure> <dl><dd>avviene a temperature e pressioni non elevate in presenza di catalizzatori metallici quali il <a href="/wiki/Platino" title="Platino">platino</a>, il <a href="/wiki/Palladio_(elemento_chimico)" title="Palladio (elemento chimico)">palladio</a> o il <a href="/wiki/Nichel" title="Nichel">nichel</a>, producendo l'<a href="/wiki/Alcani" title="Alcani">alcano</a> corrispondente.</dd> <dd>L'idrogenazione dell'alchino è talmente facile che con la maggior parte dei <a href="/wiki/Catalizzatore" title="Catalizzatore">catalizzatori</a> risulta impossibile fermare la reazione prima che questi si trasformi nell'alcano.</dd> <dd>Un modo per fermare l'idrogenazione allo stadio di alchene è quello di <i>avvelenare</i> il catalizzatore, cioè trattarlo con sostanze capaci di ridurne l'attività. Un esempio di ciò è offerto dal <b>catalizzatore di Lindlar</b> che consiste in <a href="/wiki/Palladio_(elemento_chimico)" title="Palladio (elemento chimico)">palladio</a> metallico depositato su cristalli di <a href="/wiki/Solfato_di_bario" title="Solfato di bario">solfato di bario</a> e parzialmente disattivato con <a href="/wiki/Chinolina" title="Chinolina">chinolina</a>. Tale catalizzatore manifesta ancora una sufficiente attività nei confronti dei tripli legami, ma molto povera nei confronti dei doppi legami che, di fatto, non vengono ulteriormente ridotti. Il catalizzatore inoltre orienta la reazione in modo che da un alchino disostituito si ottenga sempre l'achene <i>cis</i>, cioè quello con i due gruppi più voluminosi sullo stesso lato del doppio legame (si veda <a href="/wiki/Formula_chimica" title="Formula chimica">formula chimica</a>).</dd></dl> <ul><li><b>riduzione con <a href="/wiki/Sodio" title="Sodio">sodio</a> e <a href="/wiki/Ammoniaca" title="Ammoniaca">ammoniaca</a> liquida</b></li></ul> <pre> R H \ / R-C≡C-R' + Na + NH<sub>3</sub> -&gt; C=C (alchene <i>trans</i>) / \ H R' </pre> <dl><dd>il trattamento dell'alchino con sodio metallico in ammoniaca liquida a -33&#160;°C porta invece all'alchene <i>trans</i> attraverso un meccanismo che prevede due addizioni alternate al triplo legame prima di un <a href="/wiki/Elettrone" title="Elettrone">elettrone</a> da parte del sodio, quindi di uno ione H<sup>+</sup> da parte dell'ammoniaca.</dd></dl> <ul><li><b>addizione di alogeni e di acidi alogenidrici</b></li></ul> <dl><dd>Avvengono in modo analogo a quanto visto per gli <a href="/wiki/Alcheni" title="Alcheni">alcheni</a> e, come in quel caso, l'orientamento della reazione segue la <a href="/wiki/Regola_di_Markovnikov" title="Regola di Markovnikov">regola di Markovnikov</a>.</dd> <dd>Valgono considerazioni simili a quelle fatte a proposito dell'addizione di idrogeno, ovvero, è possibile fermare l'addizione di alogeno o acido alogenidrico al primo stadio ricorrendo a catalizzatori opportunamente avvelenati o operando a basse temperature. Il prodotto di addizione di una molecola di alogeno forma il <i>trans</i>-dialoalchene.</dd></dl> <pre>R-C≡C-R' + 2 X<sub>2</sub> -&gt; RCX<sub>2</sub>-CX<sub>2</sub>R' X R' \ / R-C≡C-R' + X<sub>2</sub> -&gt; C=C (dialoalchene <i>trans</i>) / \ R X </pre> <ul><li><b>addizione di acqua</b> (formazione di <a href="/wiki/Chetoni" title="Chetoni">chetoni</a>)</li></ul> <dl><dd>Il trattamento di un alchino con <a href="/wiki/Acido_solforico" title="Acido solforico">acido solforico</a> diluito in presenza di sali di <a href="/wiki/Mercurio_(elemento_chimico)" title="Mercurio (elemento chimico)">mercurio</a> porta alla formazione di un <i><a href="/wiki/Alcoli" title="Alcoli">alcol</a> vinilico</i>, instabile, che si trasforma nel chetone corrispondente</dd></dl> <pre> H R' \ / R-C≡C-R' + H<sub>2</sub>O -&gt; C=C -&gt; R-CH<sub>2</sub>-C=O / \ | R OH R' </pre> <p>dato che l'addizione avviene secondo la regola di Markovnikov, l'addizione di acqua ad alchini monosostituiti produce sempre i metil-chetoni corrispondenti </p> <pre>R-C≡C-H + H<sub>2</sub>O -&gt; R-C=O | CH<sub>3</sub> </pre> <ul><li><b>idroborazione-ossidazione</b></li></ul> <dl><dd>È simile nei risultati alla precedente (addizione di una molecola di acqua), salvo che l'addizione avviene secondo un orientamento anti-Markovnikov; con gli alchini monosostituiti produce dunque le <a href="/wiki/Aldeidi" title="Aldeidi">aldeidi</a> corrispondenti</dd></dl> <pre> H H \ / H<sub>2</sub>O<sub>2</sub>, OH<sup>-</sup> R-C≡C-H + BH<sub>3</sub> -&gt; C=C -&gt; R-CH<sub>2</sub>-COH / \ R BH<sub>2</sub> </pre> <ul><li><b>ossidazione</b></li></ul> <dl><dd>Il trattamento con <a href="/wiki/Potassio_permanganato" class="mw-redirect" title="Potassio permanganato">potassio permanganato</a> in <a href="/wiki/Soluzione_acquosa" title="Soluzione acquosa">soluzione acquosa</a> a freddo porta alla formazione di 1,2-di<a href="/wiki/Chetoni" title="Chetoni">chetoni</a></dd></dl> <pre>R-C≡C-R' + KMnO<sub>4</sub> --&gt; R-CO-CO-R' </pre> <dl><dd>in condizioni più vigorose - ad esempio, scaldando - l'ossidazione procede e porta alla scissione dell'alchino</dd></dl> <pre>R-C≡C-R' + KMnO<sub>4</sub> --&gt; R-COOH + R'-COOH </pre> <dl><dd>gli alchini terminali in ambiente ossidante possono subire una reazione di accoppiamento (<a href="/wiki/Reazione_di_Glaser" class="mw-redirect" title="Reazione di Glaser">reazione di Glaser</a>)</dd></dl> <pre>2 R-C≡C-H + O<sub>2</sub> --&gt; R-C≡C-C≡C-R </pre> <ul><li><b>polimerizzazione</b></li></ul> <dl><dd>Gli alchini possono polimerizzare secondo un meccanismo analogo a quanto visto per gli <a href="/wiki/Alcheni" title="Alcheni">alcheni</a>; in particolari condizioni è stato prodotto in laboratorio il <a href="/wiki/Poliacetilene" title="Poliacetilene">poliacetilene</a>, un <a href="/wiki/Polimero" title="Polimero">polimero</a> la cui struttura è quella un <a href="/wiki/Polieni" title="Polieni">poliene coniugato</a> di migliaia di atomi di lunghezza. Molecole di questo genere sono interessanti in quanto, per drogaggio, diventano conduttori di <a href="/wiki/Corrente_elettrica" title="Corrente elettrica">corrente elettrica</a>.</dd></dl> <div class="mw-heading mw-heading2"><h2 id="Note">Note</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alchini&amp;veaction=edit&amp;section=5" title="Modifica la sezione Note" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alchini&amp;action=edit&amp;section=5" title="Edit section&#039;s source code: Note"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><a href="#cite_ref-1"><b>^</b></a> <span class="reference-text">(<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>) <a rel="nofollow" class="external text" href="http://goldbook.iupac.org/A00236.html">IUPAC Gold Book, "alkynes"</a></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Bibliografia">Bibliografia</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alchini&amp;veaction=edit&amp;section=6" title="Modifica la sezione Bibliografia" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alchini&amp;action=edit&amp;section=6" title="Edit section&#039;s source code: Bibliografia"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><cite id="CITEREFSolomons" class="citation libro" style="font-style:normal"> T. W. Graham Solomons, <span style="font-style:italic;">Chimica organica</span>, 2ª&#160;ed., Bologna, Zanichelli, 2001, pp.&#160;50-51, 334-360, <a href="/wiki/ISBN" title="ISBN">ISBN</a>&#160;<a href="/wiki/Speciale:RicercaISBN/88-08-09414-6" title="Speciale:RicercaISBN/88-08-09414-6">88-08-09414-6</a>.</cite></li> <li><cite id="CITEREFHart" class="citation libro" style="font-style:normal"> Harold Hart, Christopher M Hadad, Leslie E Craine, David J Hart, <span style="font-style:italic;">Chimica organica</span>, 7ª&#160;ed., Bologna, Zanichelli, 2012, pp.&#160;67-107, <a href="/wiki/ISBN" title="ISBN">ISBN</a>&#160;<a href="/wiki/Speciale:RicercaISBN/978-8-808-19350-6" title="Speciale:RicercaISBN/978-8-808-19350-6">978-8-808-19350-6</a>.</cite></li></ul> <div class="mw-heading mw-heading2"><h2 id="Voci_correlate">Voci correlate</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alchini&amp;veaction=edit&amp;section=7" title="Modifica la sezione Voci correlate" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alchini&amp;action=edit&amp;section=7" title="Edit section&#039;s source code: Voci correlate"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Sistematica_organica" title="Sistematica organica">Sistematica organica</a></li> <li><a href="/wiki/Idrocarburi" title="Idrocarburi">Idrocarburi</a></li> <li><a href="/wiki/Cicloalchini" title="Cicloalchini">Cicloalchini</a></li> <li><a href="/wiki/Alcani" title="Alcani">Alcani</a></li> <li><a href="/wiki/Alcheni" title="Alcheni">Alcheni</a></li> <li><a href="/wiki/Acetiluri" title="Acetiluri">Acetiluri</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Altri_progetti">Altri progetti</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alchini&amp;veaction=edit&amp;section=8" title="Modifica la sezione Altri progetti" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alchini&amp;action=edit&amp;section=8" title="Edit section&#039;s source code: Altri progetti"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <div id="interProject" class="toccolours" style="display: none; clear: both; margin-top: 2em"><p id="sisterProjects" style="background-color: #efefef; color: black; font-weight: bold; margin: 0"><span>Altri progetti</span></p><ul title="Collegamenti verso gli altri progetti Wikimedia"> <li class="" title=""><a href="https://it.wiktionary.org/wiki/alchino" class="extiw" title="wikt:alchino">Wikizionario</a></li> <li class="" title=""><span class="plainlinks" title="commons:Category:Alkynes"><a class="external text" href="https://commons.wikimedia.org/wiki/Category:Alkynes?uselang=it">Wikimedia Commons</a></span></li></ul></div> <ul><li><span typeof="mw:File"><a href="https://it.wiktionary.org/wiki/" title="Collabora a Wikizionario"><img alt="Collabora a Wikizionario" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Wiktionary_small.svg/18px-Wiktionary_small.svg.png" decoding="async" width="18" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Wiktionary_small.svg/27px-Wiktionary_small.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Wiktionary_small.svg/36px-Wiktionary_small.svg.png 2x" data-file-width="350" data-file-height="350" /></a></span> <a href="https://it.wiktionary.org/wiki/" class="extiw" title="wikt:">Wikizionario</a> contiene il lemma di dizionario «<b><a href="https://it.wiktionary.org/wiki/alchino" class="extiw" title="wikt:alchino">alchini</a></b>»</li> <li><span typeof="mw:File"><a href="https://commons.wikimedia.org/wiki/?uselang=it" title="Collabora a Wikimedia Commons"><img alt="Collabora a Wikimedia Commons" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png" decoding="async" width="18" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Commons-logo.svg/27px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Commons-logo.svg/36px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></a></span> <span class="plainlinks"><a class="external text" href="https://commons.wikimedia.org/wiki/?uselang=it">Wikimedia Commons</a></span> contiene immagini o altri file su <b><span class="plainlinks"><a class="external text" href="https://commons.wikimedia.org/wiki/Category:Alkynes?uselang=it">alchini</a></span></b></li></ul> <div class="mw-heading mw-heading2"><h2 id="Collegamenti_esterni">Collegamenti esterni</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alchini&amp;veaction=edit&amp;section=9" title="Modifica la sezione Collegamenti esterni" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alchini&amp;action=edit&amp;section=9" title="Edit section&#039;s source code: Collegamenti esterni"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li class="mw-empty-elt"></li> <li><cite id="CITEREFBritannica.com" class="citation web" style="font-style:normal">(<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>) <a rel="nofollow" class="external text" href="https://www.britannica.com/science/alkyne"><span style="font-style:italic;">alkyne</span></a>, su <span style="font-style:italic;"><a href="/wiki/Enciclopedia_Britannica" title="Enciclopedia Britannica">Enciclopedia Britannica</a></span>, Encyclopædia Britannica, Inc.</cite> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q159226#P1417" title="Modifica su Wikidata"><img alt="Modifica su Wikidata" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Blue_pencil.svg/10px-Blue_pencil.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Blue_pencil.svg/15px-Blue_pencil.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/73/Blue_pencil.svg/20px-Blue_pencil.svg.png 2x" data-file-width="600" data-file-height="600" /></a></span></li> <li><cite class="citation web" style="font-style:normal"> <a rel="nofollow" class="external text" href="http://www.itchiavari.org/chimica/lab/alchini.html"><span style="font-style:italic;">Esperienze in laboratorio - Gli alchini</span></a>, su <span style="font-style:italic;">itchiavari.org</span>.</cite></li></ul> <style data-mw-deduplicate="TemplateStyles:r141815314">.mw-parser-output .navbox{border:1px solid #aaa;clear:both;margin:auto;padding:2px;width:100%}.mw-parser-output .navbox th{padding-left:1em;padding-right:1em;text-align:center}.mw-parser-output .navbox>tbody>tr:first-child>th{background:#ccf;font-size:90%;width:100%;color:var(--color-base,black)}.mw-parser-output .navbox_navbar{float:left;margin:0;padding:0 10px 0 0;text-align:left;width:6em}.mw-parser-output .navbox_title{font-size:110%}.mw-parser-output .navbox_abovebelow{background:#ddf;font-size:90%;font-weight:normal}.mw-parser-output .navbox_group{background:#ddf;font-size:90%;padding:0 10px;white-space:nowrap}.mw-parser-output .navbox_list{font-size:90%;width:100%}.mw-parser-output .navbox_list a{white-space:nowrap}html:not(.vector-feature-night-mode-enabled) .mw-parser-output .navbox_odd{background:#fdfdfd;color:var(--color-base,black)}html:not(.vector-feature-night-mode-enabled) .mw-parser-output .navbox_even{background:#f7f7f7;color:var(--color-base,black)}.mw-parser-output .navbox a.mw-selflink{color:var(--color-base,black)}.mw-parser-output .navbox_center{text-align:center}.mw-parser-output .navbox .navbox_image{padding-left:7px;vertical-align:middle;width:0}.mw-parser-output .navbox+.navbox{margin-top:-1px}.mw-parser-output .navbox .mw-collapsible-toggle{font-weight:normal;text-align:right;width:7em}body.skin--responsive .mw-parser-output .navbox_image img{max-width:none!important}.mw-parser-output .subnavbox{margin:-3px;width:100%}.mw-parser-output .subnavbox_group{background:#e6e6ff;padding:0 10px}@media screen{html.skin-theme-clientpref-night .mw-parser-output .navbox>tbody>tr:first-child>th{background:var(--background-color-interactive)!important}html.skin-theme-clientpref-night .mw-parser-output .navbox th{color:var(--color-base)!important}html.skin-theme-clientpref-night .mw-parser-output .navbox_abovebelow,html.skin-theme-clientpref-night .mw-parser-output .navbox_group{background:var(--background-color-interactive-subtle)!important}html.skin-theme-clientpref-night .mw-parser-output .subnavbox_group{background:var(--background-color-neutral-subtle)!important}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbox>tbody>tr:first-child>th{background:var(--background-color-interactive)!important}html.skin-theme-clientpref-os .mw-parser-output .navbox th{color:var(--color-base)!important}html.skin-theme-clientpref-os .mw-parser-output .navbox_abovebelow,html.skin-theme-clientpref-os .mw-parser-output .navbox_group{background:var(--background-color-interactive-subtle)!important}html.skin-theme-clientpref-os .mw-parser-output .subnavbox_group{background:var(--background-color-neutral-subtle)!important}}</style><table class="navbox mw-collapsible mw-collapsed noprint metadata" id="navbox-Sistematica_organica"><tbody><tr><th colspan="2" style="background:azzurro;"><div class="navbox_navbar"><div class="noprint plainlinks" style="background-color:transparent; padding:0; font-size:xx-small; color:var(--color-base, #000000); white-space:nowrap;"><a href="/wiki/Template:Sistematica_organica" title="Template:Sistematica organica"><span title="Vai alla pagina del template">V</span></a>&#160;·&#160;<a href="/w/index.php?title=Discussioni_template:Sistematica_organica&amp;action=edit&amp;redlink=1" class="new" title="Discussioni template:Sistematica organica (la pagina non esiste)"><span title="Discuti del template">D</span></a>&#160;·&#160;<a class="external text" href="https://it.wikipedia.org/w/index.php?title=Template:Sistematica_organica&amp;action=edit"><span title="Modifica il template. Usa l&#39;anteprima prima di salvare">M</span></a></div></div><span class="navbox_title"><a href="/wiki/Sistematica_organica" title="Sistematica organica">Sistematica organica</a></span></th></tr><tr><th colspan="1" class="navbox_group" style="background:azzurro;"><a href="/wiki/Composti_alifatici" title="Composti alifatici">Composti alifatici</a></th><td colspan="1" class="navbox_list navbox_odd"><a href="/wiki/Acetali" title="Acetali">Acetali</a> · <a href="/wiki/Acidi_carbossilici" title="Acidi carbossilici">Acidi carbossilici</a> · <a href="/wiki/Alcani" title="Alcani">Alcani</a> · <a href="/wiki/Alcheni" title="Alcheni">Alcheni</a> · <a class="mw-selflink selflink">Alchini</a> · <a href="/wiki/Alcoli" title="Alcoli">Alcoli</a> · <a href="/wiki/Aldeidi" title="Aldeidi">Aldeidi</a> · <a href="/wiki/Anidride" title="Anidride">Anidridi</a> · <a href="/wiki/Annuleni" title="Annuleni">Annuleni</a> · <a href="/wiki/Chetali" title="Chetali">Chetali</a> · <a href="/wiki/Chetoni" title="Chetoni">Chetoni</a> · <a href="/wiki/Cicloalcani" title="Cicloalcani">Cicloalcani</a> · <a href="/wiki/Cicloalcheni" title="Cicloalcheni">Cicloalcheni</a> · <a href="/wiki/Dioli" title="Dioli">Dioli</a> · <a href="/wiki/Enoli" title="Enoli">Enoli</a> · <a href="/wiki/Epossidi" title="Epossidi">Epossidi</a> · <a href="/wiki/Esteri" title="Esteri">Esteri</a> · <a href="/wiki/Eteri" title="Eteri">Eteri</a> · <a href="/wiki/Eteri_corona" title="Eteri corona">Eteri corona</a> · <a href="/wiki/Lattoni" title="Lattoni">Lattoni</a> · <a href="/wiki/Lattoli" title="Lattoli">Lattoli</a> · <a href="/wiki/Perossidi" title="Perossidi">Perossidi</a> · <a href="/wiki/Perossiacido" title="Perossiacido">Perossiacidi</a> · <a href="/wiki/Polieni" title="Polieni">Polieni</a> · <a href="/wiki/Polioli" title="Polioli">Polioli</a></td></tr><tr><th colspan="1" class="navbox_group" style="background:azzurro;"><a href="/wiki/Composti_aromatici" title="Composti aromatici">Composti aromatici</a></th><td colspan="1" class="navbox_list navbox_even"><a href="/w/index.php?title=Arini_(chimica)&amp;action=edit&amp;redlink=1" class="new" title="Arini (chimica) (la pagina non esiste)">Arini</a> · <a href="/wiki/Ciclofani" title="Ciclofani">Ciclofani</a> · <a href="/wiki/Benzene" title="Benzene">Benzene</a> · <a href="/wiki/Fenoli" title="Fenoli">Fenoli</a> · <a href="/w/index.php?title=Eterocicli_aromatici&amp;action=edit&amp;redlink=1" class="new" title="Eterocicli aromatici (la pagina non esiste)">Eterocicli aromatici</a></td></tr><tr><th colspan="1" class="navbox_group" style="background:azzurro;"><a href="/wiki/Azoto#Composti_dell&#39;azoto" title="Azoto">Contenenti azoto</a></th><td colspan="1" class="navbox_list navbox_odd"><a href="/wiki/Alcaloidi" title="Alcaloidi">Alcaloidi</a> · <a href="/wiki/Ammonio" title="Ammonio">Ammonio</a> · <a href="/wiki/Ammidi" title="Ammidi">Ammidi</a> · <a href="/wiki/Ammine" title="Ammine">Ammine</a> · <a href="/wiki/Amminali" title="Amminali">Amminali</a> · <a href="/wiki/Azine" title="Azine">Azine</a> · <a href="/wiki/Azoturo" title="Azoturo">Azidi</a> · <a href="/wiki/Azocomposti" title="Azocomposti">Azocomposti</a> · <a href="/wiki/Azoli" title="Azoli">Azoli</a> · <a href="/wiki/Carbammati" title="Carbammati">Carbammati</a> · <a href="/wiki/Cianidrine" title="Cianidrine">Cianidrine</a> · <a href="/wiki/Diazocomposti" title="Diazocomposti">Diazocomposti</a> · <a href="/wiki/Idrazoni" title="Idrazoni">Idrazoni</a> · <a href="/wiki/Immidi" title="Immidi">Immidi</a> · <a href="/wiki/Immine" title="Immine">Immine</a> · <a href="/wiki/Isocianati" title="Isocianati">Isocianati</a> · <a href="/wiki/Isocianuri" title="Isocianuri">Isocianuri</a> · <a href="/wiki/Isotiocianati" title="Isotiocianati">Isotiocianati</a> · <a href="/wiki/Lattami" title="Lattami">Lattami</a> · <a href="/wiki/Nitrili" title="Nitrili">Nitrili</a> · <a href="/wiki/Nitroderivati" title="Nitroderivati">Nitrocomposti</a> · <a href="/wiki/Nitrosocomposti" class="mw-redirect" title="Nitrosocomposti">Nitrosocomposti</a> · <a href="/wiki/Osazoni" title="Osazoni">Osazoni</a> · <a href="/wiki/Ossima" title="Ossima">Ossime</a></td></tr><tr><th colspan="1" class="navbox_group" style="background:azzurro;"><a href="/wiki/Zolfo#Composti_dello_zolfo" title="Zolfo">Contenenti zolfo</a></th><td colspan="1" class="navbox_list navbox_even"><a href="/wiki/Acidi_solfonici" title="Acidi solfonici">Acidi solfonici</a> · <a href="/wiki/Ditiani" title="Ditiani">Ditiani</a> · <a href="/wiki/Isotiocianati" title="Isotiocianati">Isotiocianati</a> · <a href="/wiki/Solfoni" title="Solfoni">Solfoni</a> · <a href="/wiki/Solfossidi" title="Solfossidi">Solfossidi</a> · <a href="/wiki/Tioesteri" title="Tioesteri">Tioesteri</a> · <a href="/wiki/Tioeteri" title="Tioeteri">Tioeteri</a> · <a href="/wiki/Tioli" title="Tioli">Tioli</a> · <a href="/wiki/Tioacetali" title="Tioacetali">Tioacetali</a> · <a href="/wiki/Tiochetali" title="Tiochetali">Tiochetali</a></td></tr><tr><th colspan="1" class="navbox_group" style="background:azzurro;"><a href="/wiki/Alogenuro" title="Alogenuro">Contenenti alogeni</a></th><td colspan="1" class="navbox_list navbox_odd"><a href="/wiki/Alogenuri_acilici" title="Alogenuri acilici">Alogenuri acilici</a> · <a href="/wiki/Alogenuri_alchilici" title="Alogenuri alchilici">Alogenuri alchilici</a></td></tr><tr><th colspan="1" class="navbox_group" style="background:azzurro;"><a href="/wiki/Silicio#Composti" title="Silicio">Contenenti silicio</a></th><td colspan="1" class="navbox_list navbox_even"><a href="/wiki/Silani" title="Silani">Silani</a> · <a href="/w/index.php?title=Sililalchini&amp;action=edit&amp;redlink=1" class="new" title="Sililalchini (la pagina non esiste)">Sililalchini</a> · <a href="/w/index.php?title=Sililalogenuri&amp;action=edit&amp;redlink=1" class="new" title="Sililalogenuri (la pagina non esiste)">Sililalogenuri</a> · <a href="/w/index.php?title=Sililidruri&amp;action=edit&amp;redlink=1" class="new" title="Sililidruri (la pagina non esiste)">Sililidruri</a> · <a href="/w/index.php?title=Silanoli&amp;action=edit&amp;redlink=1" class="new" title="Silanoli (la pagina non esiste)">Silanoli</a> · <a href="/wiki/Alcossisilani" title="Alcossisilani">Alcossisilani</a> · <a href="/wiki/Silossani" title="Silossani">Silossani</a> · <a href="/w/index.php?title=Silazani&amp;action=edit&amp;redlink=1" class="new" title="Silazani (la pagina non esiste)">Silazani</a></td></tr><tr><th colspan="1" class="navbox_group" style="background:azzurro;">Altro</th><td colspan="1" class="navbox_list navbox_odd"><a href="/wiki/Alcossido" title="Alcossido">Alcossidi</a> · <a href="/wiki/Idrocarburi" title="Idrocarburi">Idrocarburi</a> · <a href="/wiki/Stannani" title="Stannani">Stannani</a> · <a href="/wiki/Terpeni" title="Terpeni">Terpeni</a></td></tr><tr><th colspan="2" class="navbox_abovebelow">Vedi pure <i><a href="/wiki/Nomenclatura_IUPAC_dei_composti_organici" title="Nomenclatura IUPAC dei composti organici">Nomenclatura IUPAC dei composti organici</a></i></th></tr></tbody></table> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r141815314"><table class="navbox mw-collapsible mw-collapsed noprint metadata" id="navbox-Idrocarburi"><tbody><tr><th colspan="2" style="background:azzurro;"><div class="navbox_navbar"><div class="noprint plainlinks" style="background-color:transparent; padding:0; font-size:xx-small; color:var(--color-base, #000000); white-space:nowrap;"><a href="/wiki/Template:Idrocarburi" title="Template:Idrocarburi"><span title="Vai alla pagina del template">V</span></a>&#160;·&#160;<a href="/w/index.php?title=Discussioni_template:Idrocarburi&amp;action=edit&amp;redlink=1" class="new" title="Discussioni template:Idrocarburi (la pagina non esiste)"><span title="Discuti del template">D</span></a>&#160;·&#160;<a class="external text" href="https://it.wikipedia.org/w/index.php?title=Template:Idrocarburi&amp;action=edit"><span title="Modifica il template. Usa l&#39;anteprima prima di salvare">M</span></a></div></div><span class="navbox_title"><a href="/wiki/Idrocarburi" title="Idrocarburi">Idrocarburi</a></span></th></tr><tr><th colspan="1" class="navbox_group">Idrocarburi<br /><a href="/wiki/Composti_alifatici" title="Composti alifatici">alifatici</a></th><td colspan="1" class="navbox_list navbox_odd"><table class="subnavbox"><tbody><tr><th class="subnavbox_group" style="width:15em;">Idrocarburi alifatici saturi (<a href="/wiki/Alcani" title="Alcani">Alcani</a>)</th><td colspan="1"><table class="subnavbox"><tbody><tr><th class="subnavbox_group">Alcani lineari</th><td colspan="1"><a href="/wiki/Metano" title="Metano">Metano</a> · <a href="/wiki/Etano" title="Etano">Etano</a> · <a href="/wiki/Propano" title="Propano">Propano</a> · <a href="/wiki/Butano" title="Butano">Butano</a> · <a href="/wiki/Pentano" title="Pentano">Pentano</a> · <a href="/wiki/Esano" title="Esano">Esano</a> · <a href="/wiki/Eptano" title="Eptano">Eptano</a> · <a href="/wiki/Ottano" title="Ottano">Ottano</a> · <a href="/wiki/Nonano" title="Nonano">Nonano</a> · <a href="/wiki/Decano_(idrocarburo)" title="Decano (idrocarburo)">Decano</a> · <a href="/wiki/Undecano" title="Undecano">Undecano</a> · <a href="/wiki/Dodecano" title="Dodecano">Dodecano</a> · <a href="/wiki/Tridecano" title="Tridecano">Tridecano</a> · <a href="/w/index.php?title=Tetradecano&amp;action=edit&amp;redlink=1" class="new" title="Tetradecano (la pagina non esiste)">Tetradecano</a> · <a href="/w/index.php?title=Pentadecano&amp;action=edit&amp;redlink=1" class="new" title="Pentadecano (la pagina non esiste)">Pentadecano</a> · <a href="/wiki/Esadecano" title="Esadecano">Esadecano</a> · <a href="/w/index.php?title=Eptadecano&amp;action=edit&amp;redlink=1" class="new" title="Eptadecano (la pagina non esiste)">Eptadecano</a> · <a href="/w/index.php?title=Ottadecano&amp;action=edit&amp;redlink=1" class="new" title="Ottadecano (la pagina non esiste)">Ottadecano</a> · <a href="/w/index.php?title=Nonadecano&amp;action=edit&amp;redlink=1" class="new" title="Nonadecano (la pagina non esiste)">Nonadecano</a> · <a href="/wiki/Eicosano" title="Eicosano">Eicosano</a> · <a href="/w/index.php?title=Eneicosano&amp;action=edit&amp;redlink=1" class="new" title="Eneicosano (la pagina non esiste)">Eneicosano</a> · <a href="/w/index.php?title=Docosano&amp;action=edit&amp;redlink=1" class="new" title="Docosano (la pagina non esiste)">Docosano</a> · <a href="/w/index.php?title=Tricosano&amp;action=edit&amp;redlink=1" class="new" title="Tricosano (la pagina non esiste)">Tricosano</a> · <a href="/w/index.php?title=Triacontano&amp;action=edit&amp;redlink=1" class="new" title="Triacontano (la pagina non esiste)">Triacontano</a> · <a href="/wiki/Entriacontano" title="Entriacontano">Entriacontano</a> · <a href="/w/index.php?title=Tetracontano&amp;action=edit&amp;redlink=1" class="new" title="Tetracontano (la pagina non esiste)">Tetracontano</a> · <a href="/w/index.php?title=Pentacontano&amp;action=edit&amp;redlink=1" class="new" title="Pentacontano (la pagina non esiste)">Pentacontano</a> · <a href="/w/index.php?title=Esacontano&amp;action=edit&amp;redlink=1" class="new" title="Esacontano (la pagina non esiste)">Esacontano</a> · <a href="/w/index.php?title=Eptacontano&amp;action=edit&amp;redlink=1" class="new" title="Eptacontano (la pagina non esiste)">Eptacontano</a> · <a href="/w/index.php?title=Ottacontano&amp;action=edit&amp;redlink=1" class="new" title="Ottacontano (la pagina non esiste)">Ottacontano</a> · <a href="/w/index.php?title=Nonacontano&amp;action=edit&amp;redlink=1" class="new" title="Nonacontano (la pagina non esiste)">Nonacontano</a> · <a href="/w/index.php?title=Ectano&amp;action=edit&amp;redlink=1" class="new" title="Ectano (la pagina non esiste)">Ectano</a></td></tr><tr><th class="subnavbox_group">Alcani ramificati</th><td colspan="1"><a href="/wiki/Isobutano" title="Isobutano">Isobutano</a> · <a href="/wiki/Isopentano" title="Isopentano">Isopentano</a> · <a href="/wiki/3-metilpentano" title="3-metilpentano">3-metilpentano</a> · <a href="/wiki/Neopentano" title="Neopentano">Neopentano</a> · <a href="/wiki/Isoesano" title="Isoesano">Isoesano</a> · <a href="/wiki/Isoeptano" title="Isoeptano">Isoeptano</a> · <a href="/wiki/Isoottano" title="Isoottano">Isoottano</a> · <a href="/w/index.php?title=Isononano&amp;action=edit&amp;redlink=1" class="new" title="Isononano (la pagina non esiste)">Isononano</a> · <a href="/w/index.php?title=Isodecano&amp;action=edit&amp;redlink=1" class="new" title="Isodecano (la pagina non esiste)">Isodecano</a></td></tr><tr><th class="subnavbox_group"><a href="/wiki/Cicloalcani" title="Cicloalcani">Cicloalcani</a></th><td colspan="1"><a href="/wiki/Ciclopropano" title="Ciclopropano">Ciclopropano</a> · <a href="/wiki/Ciclobutano" title="Ciclobutano">Ciclobutano</a> · <a href="/wiki/Ciclopentano" title="Ciclopentano">Ciclopentano</a> · <a href="/wiki/Cicloesano" title="Cicloesano">Cicloesano</a> · <a href="/wiki/Cicloeptano" title="Cicloeptano">Cicloeptano</a> · <a href="/wiki/Cicloottano" title="Cicloottano">Cicloottano</a> · <a href="/w/index.php?title=Ciclononano&amp;action=edit&amp;redlink=1" class="new" title="Ciclononano (la pagina non esiste)">Ciclononano</a> · <a href="/w/index.php?title=Ciclodecano&amp;action=edit&amp;redlink=1" class="new" title="Ciclodecano (la pagina non esiste)">Ciclodecano</a> · <a href="/wiki/Cicloundecano" title="Cicloundecano">Cicloundecano</a> · <a href="/wiki/Ciclododecano" title="Ciclododecano">Ciclododecano</a> · <a href="/w/index.php?title=Ciclopentadecano&amp;action=edit&amp;redlink=1" class="new" title="Ciclopentadecano (la pagina non esiste)">Ciclopentadecano</a></td></tr><tr><th class="subnavbox_group"><a href="/w/index.php?title=Alchilcicloalcani&amp;action=edit&amp;redlink=1" class="new" title="Alchilcicloalcani (la pagina non esiste)">Alchilcicloalcani</a></th><td colspan="1"><a href="/wiki/Metilciclopropano" title="Metilciclopropano">Metilciclopropano</a> · <a href="/w/index.php?title=Metilciclobutano&amp;action=edit&amp;redlink=1" class="new" title="Metilciclobutano (la pagina non esiste)">Metilciclobutano</a> · <a href="/wiki/Metilciclopentano" title="Metilciclopentano">Metilciclopentano</a> · <a href="/wiki/Metilcicloesano" title="Metilcicloesano">Metilcicloesano</a> · <a href="/w/index.php?title=Isopropilcicloesano&amp;action=edit&amp;redlink=1" class="new" title="Isopropilcicloesano (la pagina non esiste)">Isopropilcicloesano</a> ·</td></tr><tr><th class="subnavbox_group"><a href="/wiki/Bicicloalcani" title="Bicicloalcani">Bicicloalcani</a></th><td colspan="1"><a href="/wiki/Casano" title="Casano">Casano</a> · <a href="/wiki/Norbornano" title="Norbornano">Norbornano</a> · <a href="/wiki/Decalina" title="Decalina">Decalina</a></td></tr><tr><th class="subnavbox_group"><a href="/w/index.php?title=Policicloalcani&amp;action=edit&amp;redlink=1" class="new" title="Policicloalcani (la pagina non esiste)">Policicloalcani</a></th><td colspan="1"><a href="/wiki/Adamantano" title="Adamantano">Adamantano</a> · <a href="/wiki/Diamantoidi" title="Diamantoidi">Diamantoidi</a> · <a href="/wiki/Peridrofenantrene" title="Peridrofenantrene">Peridrofenantrene</a> · <a href="/wiki/Peridrociclopentanofenantrene" class="mw-redirect" title="Peridrociclopentanofenantrene">Peridrociclopentanofenantrene</a> · <a href="/wiki/Cubano" title="Cubano">Cubano</a> · <a href="/wiki/Prismano" title="Prismano">Prismano</a> · <a href="/wiki/Dodecaedrano" title="Dodecaedrano">Dodecaedrano</a> · <a href="/wiki/Basketano" title="Basketano">Basketano</a> · <a href="/w/index.php?title=Chiesano&amp;action=edit&amp;redlink=1" class="new" title="Chiesano (la pagina non esiste)">Chiesano</a> · <a href="/wiki/Pagodano" title="Pagodano">Pagodano</a> · <a href="/wiki/Tetraedrano" title="Tetraedrano">Tetraedrano</a> · <a href="/w/index.php?title=Twistano&amp;action=edit&amp;redlink=1" class="new" title="Twistano (la pagina non esiste)">Twistano</a></td></tr><tr><th class="subnavbox_group"><a href="/wiki/Spiroalcani" title="Spiroalcani">Spiroalcani</a></th><td colspan="1"><a href="/wiki/Bullvalene" title="Bullvalene">Bullvalene</a></td></tr></tbody></table></td></tr><tr><th class="subnavbox_group" style="width:15em;">Idrocarburi alifatici insaturi (<a href="/wiki/Alcheni" title="Alcheni">Alcheni</a> e <a class="mw-selflink selflink">Alchini</a>)</th><td colspan="1"><table class="subnavbox"><tbody><tr><th class="subnavbox_group" style="width:8.5em;">Alcheni lineari</th><td colspan="1"><a href="/wiki/Etilene" title="Etilene">Etilene</a> · <a href="/wiki/Propilene" title="Propilene">Propilene</a> · <a href="/wiki/Butene" title="Butene">Butene</a> · <a href="/wiki/Pentene" title="Pentene">Pentene</a> · <a href="/wiki/Esene" title="Esene">Esene</a> · <a href="/wiki/Eptene" title="Eptene">Eptene</a> · <a href="/wiki/Ottene" title="Ottene">Ottene</a></td></tr><tr><th class="subnavbox_group" style="width:8.5em;">Alcheni ramificati</th><td colspan="1"><a href="/wiki/Isobutene" title="Isobutene">Isobutene</a> · <a href="/w/index.php?title=Isopentene&amp;action=edit&amp;redlink=1" class="new" title="Isopentene (la pagina non esiste)">Isopentene</a> · <a href="/w/index.php?title=Neopentene&amp;action=edit&amp;redlink=1" class="new" title="Neopentene (la pagina non esiste)">Neopentene</a> · <a href="/w/index.php?title=Isoesene&amp;action=edit&amp;redlink=1" class="new" title="Isoesene (la pagina non esiste)">Isoesene</a> · <a href="/w/index.php?title=Isoeptene&amp;action=edit&amp;redlink=1" class="new" title="Isoeptene (la pagina non esiste)">Isoeptene</a> · <a href="/w/index.php?title=Isoottene&amp;action=edit&amp;redlink=1" class="new" title="Isoottene (la pagina non esiste)">Isoottene</a></td></tr><tr><th class="subnavbox_group" style="width:8.5em;"><a href="/wiki/Alcadieni" class="mw-redirect" title="Alcadieni">Alcadieni</a></th><td colspan="1"><a href="/wiki/Allene" class="mw-redirect" title="Allene">Allene</a> · <a href="/wiki/Butadiene" title="Butadiene">Butadiene</a> · <a href="/wiki/Pentadiene" title="Pentadiene">Pentadiene</a> · <a href="/w/index.php?title=Esadiene&amp;action=edit&amp;redlink=1" class="new" title="Esadiene (la pagina non esiste)">Esadiene</a> · <a href="/wiki/Isoprene" title="Isoprene">Isoprene</a> · <a href="/wiki/1,3-cicloesadiene" title="1,3-cicloesadiene">1,3-cicloesadiene</a> · <a href="/wiki/1,4-cicloesadiene" title="1,4-cicloesadiene">1,4-cicloesadiene</a> · <a href="/wiki/1,5-Cicloottadiene" class="mw-redirect" title="1,5-Cicloottadiene">1,5-Cicloottadiene</a> · <a href="/wiki/Norbornadiene" title="Norbornadiene">Norbornadiene</a></td></tr><tr><th class="subnavbox_group" style="width:8.5em;"><a href="/wiki/Cicloalcheni" title="Cicloalcheni">Cicloalcheni</a></th><td colspan="1"><a href="/wiki/Ciclopropene" title="Ciclopropene">Ciclopropene</a> · <a href="/wiki/Ciclobutene" title="Ciclobutene">Ciclobutene</a> · <a href="/wiki/Ciclopentene" title="Ciclopentene">Ciclopentene</a> · <a href="/wiki/Cicloesene" title="Cicloesene">Cicloesene</a> · <a href="/w/index.php?title=Cicloeptene&amp;action=edit&amp;redlink=1" class="new" title="Cicloeptene (la pagina non esiste)">Cicloeptene</a> · <a href="/wiki/Cicloottene" title="Cicloottene">Cicloottene</a></td></tr><tr><th class="subnavbox_group" style="width:8.5em;"><a href="/w/index.php?title=Alchilcicloalcheni&amp;action=edit&amp;redlink=1" class="new" title="Alchilcicloalcheni (la pagina non esiste)">Alchilcicloalcheni</a></th><td colspan="1"><a href="/w/index.php?title=Metilciclopropene&amp;action=edit&amp;redlink=1" class="new" title="Metilciclopropene (la pagina non esiste)">Metilciclopropene</a> · <a href="/w/index.php?title=Metilciclobutene&amp;action=edit&amp;redlink=1" class="new" title="Metilciclobutene (la pagina non esiste)">Metilciclobutene</a> · <a href="/w/index.php?title=Metilciclopentene&amp;action=edit&amp;redlink=1" class="new" title="Metilciclopentene (la pagina non esiste)">Metilciclopentene</a> · <a href="/w/index.php?title=Metilcicloesene&amp;action=edit&amp;redlink=1" class="new" title="Metilcicloesene (la pagina non esiste)">Metilcicloesene</a> · <a href="/w/index.php?title=Isopropilcicloesene&amp;action=edit&amp;redlink=1" class="new" title="Isopropilcicloesene (la pagina non esiste)">Isopropilcicloesene</a> ·</td></tr><tr><th class="subnavbox_group" style="width:8.5em;"><a href="/w/index.php?title=Bicicloalcheni&amp;action=edit&amp;redlink=1" class="new" title="Bicicloalcheni (la pagina non esiste)">Bicicloalcheni</a></th><td colspan="1"><a href="/wiki/Norbornene" title="Norbornene">Norbornene</a></td></tr><tr><th class="subnavbox_group" style="width:8.5em;">Alchini lineari</th><td colspan="1"><a href="/wiki/Acetilene" title="Acetilene">Acetilene</a> · <a href="/wiki/Metilacetilene" class="mw-redirect" title="Metilacetilene">Metilacetilene</a> · <a href="/wiki/Butino_(chimica)" title="Butino (chimica)">Butino</a> · <a href="/wiki/Pentino" title="Pentino">Pentino</a> · <a href="/wiki/Esino_(chimica)" title="Esino (chimica)">Esino</a> · <a href="/w/index.php?title=Eptino&amp;action=edit&amp;redlink=1" class="new" title="Eptino (la pagina non esiste)">Eptino</a> · <a href="/wiki/Ottino" title="Ottino">Ottino</a></td></tr><tr><th class="subnavbox_group" style="width:8.5em;">Alchini ramificati</th><td colspan="1"><a href="/w/index.php?title=Isobutino&amp;action=edit&amp;redlink=1" class="new" title="Isobutino (la pagina non esiste)">Isobutino</a> · <a href="/w/index.php?title=Isopentino&amp;action=edit&amp;redlink=1" class="new" title="Isopentino (la pagina non esiste)">Isopentino</a> · <a href="/w/index.php?title=Neopentino&amp;action=edit&amp;redlink=1" class="new" title="Neopentino (la pagina non esiste)">Neopentino</a> · <a href="/w/index.php?title=Isoesino&amp;action=edit&amp;redlink=1" class="new" title="Isoesino (la pagina non esiste)">Isoesino</a> · <a href="/w/index.php?title=Isoeptino&amp;action=edit&amp;redlink=1" class="new" title="Isoeptino (la pagina non esiste)">Isoeptino</a> · <a href="/w/index.php?title=Isoottino&amp;action=edit&amp;redlink=1" class="new" title="Isoottino (la pagina non esiste)">Isoottino</a> · <a href="/wiki/Etilacetilene" title="Etilacetilene">Etilacetilene</a></td></tr><tr><th class="subnavbox_group" style="width:8.5em;"><a href="/wiki/Cicloalchini" title="Cicloalchini">Cicloalchini</a></th><td colspan="1"><a href="/w/index.php?title=Ciclopropino&amp;action=edit&amp;redlink=1" class="new" title="Ciclopropino (la pagina non esiste)">Ciclopropino</a> · <a href="/w/index.php?title=Ciclobutino&amp;action=edit&amp;redlink=1" class="new" title="Ciclobutino (la pagina non esiste)">Ciclobutino</a> · <a href="/w/index.php?title=Ciclopentino&amp;action=edit&amp;redlink=1" class="new" title="Ciclopentino (la pagina non esiste)">Ciclopentino</a> · <a href="/w/index.php?title=Cicloesino&amp;action=edit&amp;redlink=1" class="new" title="Cicloesino (la pagina non esiste)">Cicloesino</a> · <a href="/w/index.php?title=Cicloeptino&amp;action=edit&amp;redlink=1" class="new" title="Cicloeptino (la pagina non esiste)">Cicloeptino</a> · <a href="/wiki/Cicloottino" title="Cicloottino">Cicloottino</a></td></tr><tr><th class="subnavbox_group" style="width:8.5em;"><a href="/wiki/Cumuleni" title="Cumuleni">Cumuleni</a></th><td colspan="1"><a href="/wiki/Allene" class="mw-redirect" title="Allene">Allene</a></td></tr><tr><th class="subnavbox_group" style="width:8.5em;">Altri</th><td colspan="1"><a href="/w/index.php?title=Alcatriene&amp;action=edit&amp;redlink=1" class="new" title="Alcatriene (la pagina non esiste)">Alcatriene</a> · <a href="/w/index.php?title=Alcadiino&amp;action=edit&amp;redlink=1" class="new" title="Alcadiino (la pagina non esiste)">Alcadiino</a> · <a href="/w/index.php?title=Alchenino&amp;action=edit&amp;redlink=1" class="new" title="Alchenino (la pagina non esiste)">Alchenino</a> · <a href="/wiki/Cicloottatetraene" title="Cicloottatetraene">Cicloottatetraene</a> · <a href="/wiki/Ciclododecatriene" title="Ciclododecatriene">Ciclododecatriene</a></td></tr></tbody></table></td></tr></tbody></table></td></tr><tr><th colspan="1" class="navbox_group">Idrocarburi<br /><a href="/wiki/Composti_aromatici" title="Composti aromatici">aromatici</a></th><td colspan="1" class="navbox_list navbox_even"><table class="subnavbox"><tbody><tr><th class="subnavbox_group" style="width:15em;">Idrocarburi monociclici aromatici</th><td colspan="1"><table class="subnavbox"><tbody><tr><th class="subnavbox_group" style="width:8.5em;"><a href="/wiki/Annuleni" title="Annuleni">Annuleni</a></th><td colspan="1"><a href="/wiki/Ciclobutadiene" title="Ciclobutadiene">Ciclobutadiene</a> · <a href="/wiki/Benzene" title="Benzene">Benzene</a> · <a href="/wiki/Cicloottatetraene" title="Cicloottatetraene">Cicloottatetraene</a></td></tr><tr><th class="subnavbox_group" style="width:8.5em;"><a href="/wiki/Alchilbenzeni" title="Alchilbenzeni">Alchilbenzeni</a></th><td colspan="1"><a href="/wiki/Toluene" title="Toluene">Toluene</a> · <a href="/wiki/Xilene" title="Xilene">Xilene</a> · <a href="/wiki/Etilbenzene" title="Etilbenzene">Etilbenzene</a> · <a href="/wiki/Mesitilene" title="Mesitilene">Mesitilene</a> · <a href="/wiki/Emellitene" class="mw-redirect" title="Emellitene">Emellitene</a> · <a href="/wiki/Pseudocumene" title="Pseudocumene">Pseudocumene</a> · <a href="/wiki/Cumene" title="Cumene">Cumene</a> · <a href="/wiki/4-isopropiltoluene" title="4-isopropiltoluene">4-isopropiltoluene</a> · <a href="/wiki/Durene" title="Durene">Durene</a> · <a href="/wiki/Stirene" title="Stirene">Stirene</a> · <a href="/wiki/Fenilacetilene" title="Fenilacetilene">Fenilacetilene</a> · <a href="/wiki/Difenilmetano" title="Difenilmetano">Difenilmetano</a> · <a href="/wiki/Esametilbenzene" title="Esametilbenzene">Esametilbenzene</a> · <a href="/w/index.php?title=2-fenilesano&amp;action=edit&amp;redlink=1" class="new" title="2-fenilesano (la pagina non esiste)">2-fenilesano</a> · <a href="/w/index.php?title=1,3,5-trietilbenzene&amp;action=edit&amp;redlink=1" class="new" title="1,3,5-trietilbenzene (la pagina non esiste)">1,3,5-trietilbenzene</a></td></tr></tbody></table></td></tr><tr><th class="subnavbox_group" style="width:15em;"><a href="/wiki/Idrocarburi_policiclici_aromatici" title="Idrocarburi policiclici aromatici">Idrocarburi policiclici aromatici</a></th><td colspan="1"><table class="subnavbox"><tbody><tr><th class="subnavbox_group" style="width:8.5em;"><a href="/wiki/Aceni" title="Aceni">Aceni</a></th><td colspan="1"><a href="/wiki/Naftalene" title="Naftalene">Naftalene</a> · <a href="/wiki/Antracene" title="Antracene">Antracene</a> · <a href="/wiki/Naftacene" title="Naftacene">Naftacene</a> · <a href="/wiki/Pentacene" title="Pentacene">Pentacene</a> · <a href="/wiki/Esacene" title="Esacene">Esacene</a> · <a href="/wiki/Eptacene" title="Eptacene">Eptacene</a></td></tr><tr><th class="subnavbox_group" style="width:8.5em;">Altri</th><td colspan="1"><a href="/wiki/Fenalene" title="Fenalene">Fenalene</a> · <a href="/wiki/Fluorene" title="Fluorene">Fluorene</a> · <a href="/wiki/Infinitene" title="Infinitene">Infinitene</a> · <a href="/wiki/Kekulene" title="Kekulene">Kekulene</a> · <a href="/wiki/Zetrene" title="Zetrene">Zetrene</a> · <a href="/wiki/Eliceni" title="Eliceni">Eliceni</a> · <a href="/wiki/Circuleni" title="Circuleni">Circuleni</a> · <a href="/wiki/Indene" title="Indene">Indene</a></td></tr></tbody></table></td></tr></tbody></table></td></tr></tbody></table> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r141815314"><table class="navbox mw-collapsible mw-collapsed noprint metadata" id="navbox-Gruppi_funzionali"><tbody><tr><th colspan="2"><div class="navbox_navbar"><div class="noprint plainlinks" style="background-color:transparent; padding:0; font-size:xx-small; color:var(--color-base, #000000); white-space:nowrap;"><a href="/wiki/Template:Gruppi_funzionali" title="Template:Gruppi funzionali"><span title="Vai alla pagina del template">V</span></a>&#160;·&#160;<a href="/w/index.php?title=Discussioni_template:Gruppi_funzionali&amp;action=edit&amp;redlink=1" class="new" title="Discussioni template:Gruppi funzionali (la pagina non esiste)"><span title="Discuti del template">D</span></a>&#160;·&#160;<a class="external text" href="https://it.wikipedia.org/w/index.php?title=Template:Gruppi_funzionali&amp;action=edit"><span title="Modifica il template. Usa l&#39;anteprima prima di salvare">M</span></a></div></div><span class="navbox_title"><a href="/wiki/Gruppo_funzionale" title="Gruppo funzionale">Gruppi funzionali</a></span></th></tr><tr><th colspan="1" class="navbox_group"><a href="/wiki/Idrocarburi" title="Idrocarburi">Idrocarburi</a> (<a href="/wiki/Carbonio" title="Carbonio">C</a> e <a href="/wiki/Idrogeno" title="Idrogeno">H</a>)</th><td colspan="1" class="navbox_list navbox_odd"><a href="/wiki/Alchile" title="Alchile">Alchile</a> (<a href="/wiki/Metile" title="Metile">Metile</a>, <a href="/wiki/Etile" title="Etile">Etile</a>, <a href="/wiki/Propile" title="Propile">Propile</a>, <a href="/wiki/Butile" title="Butile">Butile</a>, <a href="/wiki/Pentile" title="Pentile">Pentile</a>)<b>&#160;·</b> <a href="/w/index.php?title=Alchenile&amp;action=edit&amp;redlink=1" class="new" title="Alchenile (la pagina non esiste)">Alchenile</a> (<a href="/wiki/Allile" title="Allile">Allile</a>, <a href="/wiki/Gruppo_vinilico" title="Gruppo vinilico">Vinile</a>)<b>&#160;·</b> <a href="/w/index.php?title=Alchinile&amp;action=edit&amp;redlink=1" class="new" title="Alchinile (la pagina non esiste)">Alchinile</a><b>&#160;·</b> <a href="/wiki/Alleni" title="Alleni">Allene</a><b>&#160;·</b> <a href="/wiki/Benzile" title="Benzile">Benzile</a><b>&#160;·</b> <a href="/wiki/Carbene" title="Carbene">Carbene</a><b>&#160;·</b> <a href="/wiki/Carbino" title="Carbino">Carbino</a><b>&#160;·</b> <a href="/wiki/Cumuleni" title="Cumuleni">Cumulene</a><b>&#160;·</b> <a href="/wiki/Metandiile" title="Metandiile">Ponte metilene</a><b>&#160;·</b> <a href="/wiki/Metilidene" title="Metilidene">Metilidene</a><b>&#160;·</b> <a href="/wiki/Metino" title="Metino">Metino</a><b>&#160;·</b> <a href="/wiki/Fenile" title="Fenile">Fenile</a></td></tr><tr><th colspan="1" class="navbox_group">Gruppi con C, H e <a href="/wiki/Ossigeno" title="Ossigeno">O</a></th><td colspan="1" class="navbox_list navbox_even"><a href="/wiki/Acetossi" title="Acetossi">Acetossi</a><b>&#160;·</b> <a href="/wiki/Acetile" title="Acetile">Acetile</a><b>&#160;·</b> <a href="/wiki/Acriloile" title="Acriloile">Acriloile</a><b>&#160;·</b> <a href="/wiki/Acile" title="Acile">Acile</a><b>&#160;·</b> <a href="/wiki/Acile#Esempi" title="Acile">Formile</a><b>&#160;·</b> <a href="/w/index.php?title=Alcossi&amp;action=edit&amp;redlink=1" class="new" title="Alcossi (la pagina non esiste)">Alcossi</a> (<a href="/wiki/Metossi" title="Metossi">Metossi</a>)<b>&#160;·</b> <a href="/wiki/Benzoile" title="Benzoile">Benzoile</a><b>&#160;·</b> <a href="/wiki/Carbonile" title="Carbonile">Carbonile</a><b>&#160;·</b> <a href="/wiki/Acidi_carbossilici" title="Acidi carbossilici">Carbossile</a><b>&#160;·</b> <a href="/wiki/Diossirano" title="Diossirano">Diossirano</a><b>&#160;·</b> <a href="/wiki/Epossidi" title="Epossidi">Epossidi</a><b>&#160;·</b> <a href="/wiki/Esteri" title="Esteri">Estere</a><b>&#160;·</b> <a href="/wiki/Eteri" title="Eteri">Etere</a><b>&#160;·</b> <a href="/w/index.php?title=Etilendiossi&amp;action=edit&amp;redlink=1" class="new" title="Etilendiossi (la pagina non esiste)">Etilendiossi</a><b>&#160;·</b> <a href="/wiki/Gruppo_ossidrilico" title="Gruppo ossidrilico">Idrossile</a><b>&#160;·</b> <a href="/wiki/Chetoni" title="Chetoni">Chetone</a><b>&#160;·</b> <a href="/wiki/Metilendiossi" title="Metilendiossi">Metilendiossi</a><b>&#160;·</b> <a href="/wiki/Perossidi" title="Perossidi">Perossido</a> (<a href="/w/index.php?title=Perossido_organico&amp;action=edit&amp;redlink=1" class="new" title="Perossido organico (la pagina non esiste)">Organico</a>)<b>&#160;·</b> <a href="/w/index.php?title=Ynone&amp;action=edit&amp;redlink=1" class="new" title="Ynone (la pagina non esiste)">Ynone</a></td></tr><tr><th colspan="1" class="navbox_group">Gruppi con C, H, O <br />e un altro atomo</th><td colspan="1" class="navbox_list navbox_odd"><table class="subnavbox"><tbody><tr><th class="subnavbox_group" style="width:7.5em"><a href="/wiki/Azoto" title="Azoto">Azoto</a></th><td colspan="1"><a href="/wiki/Ammine" title="Ammine">Ammina</a><b>&#160;·</b> <a href="/wiki/Azocomposti" title="Azocomposti">Azoico</a><b>&#160;·</b> <a href="/wiki/Cianato" title="Cianato">Cianato</a><b>&#160;·</b> <a href="/wiki/Idrazoni" title="Idrazoni">Idrazone</a><b>&#160;·</b> <a href="/wiki/Immidi" title="Immidi">Immide</a><b>&#160;·</b> <a href="/wiki/Immine" title="Immine">Immina</a><b>&#160;·</b> <a href="/wiki/Isocianati" title="Isocianati">Isocianato</a><b>&#160;·</b> <a href="/wiki/Isocianuri" title="Isocianuri">Isonitrile</a><b>&#160;·</b> <a href="/wiki/Nitrene" title="Nitrene">Nitrene</a><b>&#160;·</b> <a href="/wiki/Nitrili" title="Nitrili">Nitrile</a><b>&#160;·</b> <a href="/wiki/Nitroderivati" title="Nitroderivati">Composto nitro</a><b>&#160;·</b> <a href="/wiki/Nitrosoderivati" title="Nitrosoderivati">Composto nitroso</a><b>&#160;·</b> <a href="/wiki/Ammidi" title="Ammidi">Ammide organica</a><b>&#160;·</b> <a href="/wiki/Ossima" title="Ossima">Ossime</a></td></tr><tr><th class="subnavbox_group" style="width:7.5em"><a href="/wiki/Fosforo" title="Fosforo">Fosforo</a></th><td colspan="1"><a href="/wiki/Fosfonati" title="Fosfonati">Fosfonato</a><b>&#160;·</b> <a href="/w/index.php?title=Fosfonite&amp;action=edit&amp;redlink=1" class="new" title="Fosfonite (la pagina non esiste)">Fosfonoso</a></td></tr><tr><th class="subnavbox_group" style="width:7.5em"><a href="/wiki/Zolfo" title="Zolfo">Zolfo</a></th><td colspan="1"><a href="/wiki/Disolfuro" title="Disolfuro">Ponte S-S</a><b>&#160;·</b> <a href="/wiki/Solfoni" title="Solfoni">Solfonile</a><b>&#160;·</b> <a href="/wiki/Acidi_solfonici" title="Acidi solfonici">Idrossisolfonile</a><b>&#160;·</b> <a href="/wiki/Solfossidi" title="Solfossidi">Solfenile</a><b>&#160;·</b> <a href="/wiki/Tioaldeidi" title="Tioaldeidi">Tiocarbonile</a><b>&#160;·</b> <a href="/wiki/Tioesteri" title="Tioesteri">Tiocarbossile</a><b>&#160;·</b> <a href="/wiki/Tioeteri" title="Tioeteri">Solfuro</a><b>&#160;·</b> <a href="/w/index.php?title=Tiochetone&amp;action=edit&amp;redlink=1" class="new" title="Tiochetone (la pagina non esiste)">Tiochetone</a><b>&#160;·</b> <a href="/wiki/Tioli" title="Tioli">Tiolo</a></td></tr><tr><th class="subnavbox_group" style="width:7.5em"><a href="/wiki/Selenio" title="Selenio">Selenio</a></th><td colspan="1"><a href="/wiki/Selenoli" title="Selenoli">Selenolo</a><b>&#160;·</b> <a href="/w/index.php?title=Acido_selenonico&amp;action=edit&amp;redlink=1" class="new" title="Acido selenonico (la pagina non esiste)">Acido selenonico</a><b>&#160;·</b> <a href="/w/index.php?title=Acido_seleninico&amp;action=edit&amp;redlink=1" class="new" title="Acido seleninico (la pagina non esiste)">Acido seleninico</a><b>&#160;·</b> <a href="/w/index.php?title=Acido_selenenico&amp;action=edit&amp;redlink=1" class="new" title="Acido selenenico (la pagina non esiste)">Acido selenenico</a></td></tr><tr><th class="subnavbox_group" style="width:7.5em"><a href="/wiki/Tellurio" title="Tellurio">Tellurio</a></th><td colspan="1"><a href="/wiki/Tellurolo" title="Tellurolo">Tellurolo</a></td></tr></tbody></table></td></tr><tr><th colspan="1" class="navbox_group">Altri gruppi</th><td colspan="1" class="navbox_list navbox_even"><a href="/wiki/Isotiocianati" title="Isotiocianati">Isotiocianato</a><b>&#160;·</b> <a href="/wiki/Ammidi" title="Ammidi">Fosforoammide</a><b>&#160;·</b> <a href="/w/index.php?title=Cloruoro_sulfenile&amp;action=edit&amp;redlink=1" class="new" title="Cloruoro sulfenile (la pagina non esiste)">Cloruoro sulfenile</a><b>&#160;·</b> <a href="/wiki/Ammidi" title="Ammidi">Solfonoammide</a><b>&#160;·</b> <a href="/wiki/Tiocianato" title="Tiocianato">Tiocianato</a></td></tr><tr><th colspan="2" class="navbox_abovebelow">Vedi anche <i><a href="/w/index.php?title=Classificazione_chimica&amp;action=edit&amp;redlink=1" class="new" title="Classificazione chimica (la pagina non esiste)">Classificazione chimica</a></i>, <i><a href="/wiki/Nomenclatura_chimica" title="Nomenclatura chimica">Nomenclatura chimica</a></i> (<a href="/w/index.php?title=Nomenclatura_IUPAC_dei_composti_inorganici&amp;action=edit&amp;redlink=1" class="new" title="Nomenclatura IUPAC dei composti inorganici (la pagina non esiste)">inorganica</a>, <a href="/wiki/Nomenclatura_IUPAC_dei_composti_organici" title="Nomenclatura IUPAC dei composti organici">organica</a>)</th></tr></tbody></table> <style data-mw-deduplicate="TemplateStyles:r140554510">.mw-parser-output .CdA{border:1px solid #aaa;width:100%;margin:auto;font-size:90%;padding:2px}.mw-parser-output .CdA th{background-color:#f2f2f2;font-weight:bold;width:20%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .CdA{border-color:#54595D}html.skin-theme-clientpref-night .mw-parser-output .CdA th{background-color:#202122}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .CdA{border-color:#54595D}html.skin-theme-clientpref-os .mw-parser-output .CdA th{background-color:#202122}}</style><table class="CdA"><tbody><tr><th><a href="/wiki/Aiuto:Controllo_di_autorit%C3%A0" title="Aiuto:Controllo di autorità">Controllo di autorità</a></th><td><a href="/wiki/Nuovo_soggettario" title="Nuovo soggettario">Thesaurus BNCF</a> <span class="uid"><a rel="nofollow" class="external text" href="https://thes.bncf.firenze.sbn.it/termine.php?id=31711">31711</a></span><span style="font-weight:bold;">&#160;·</span> <a href="/wiki/Library_of_Congress_Control_Number" title="Library of Congress Control Number">LCCN</a> <span class="uid">(<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>)&#160;<a rel="nofollow" class="external text" href="http://id.loc.gov/authorities/subjects/sh97007297">sh97007297</a></span><span style="font-weight:bold;">&#160;·</span> <a href="/wiki/Gemeinsame_Normdatei" title="Gemeinsame Normdatei">GND</a> <span class="uid">(<span style="font-weight:bolder; font-size:80%"><abbr title="tedesco">DE</abbr></span>)&#160;<a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4141897-9">4141897-9</a></span><span style="font-weight:bold;">&#160;·</span> <a href="/wiki/Biblioteca_nazionale_di_Francia" title="Biblioteca nazionale di Francia">BNF</a> <span class="uid">(<span style="font-weight:bolder; font-size:80%"><abbr title="francese">FR</abbr></span>)&#160;<a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb12271406n">cb12271406n</a> <a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb12271406n">(data)</a></span><span style="font-weight:bold;">&#160;·</span> <a href="/wiki/Biblioteca_nazionale_di_Israele" title="Biblioteca nazionale di Israele">J9U</a> <span class="uid">(<span style="font-weight:bolder; font-size:80%"><abbr 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