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class="vector-toc-link" href="#Reattività_generale"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Reattività generale</span> </div> </a> <ul id="toc-Reattività_generale-sublist" class="vector-toc-list"> </ul> </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">3</span> <span>Nomenclatura IUPAC</span> </div> </a> <ul id="toc-Nomenclatura_IUPAC-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reazione_con_metalli" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reazione_con_metalli"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Reazione con metalli</span> </div> </a> <ul id="toc-Reazione_con_metalli-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Preparazioni" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Preparazioni"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Preparazioni</span> </div> </a> <ul id="toc-Preparazioni-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">6</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">7</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">8</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">9</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">10</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'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'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">Alogenuri alchilici</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'altra lingua. Disponibile in 48 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-48" 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">48 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/Halogenoalkaan" title="Halogenoalkaan - afrikaans" lang="af" hreflang="af" data-title="Halogenoalkaan" 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/%D9%87%D8%A7%D9%84%D9%8A%D8%AF_%D8%A7%D9%84%D8%A3%D9%84%D9%83%D9%8A%D9%84" title="هاليد الألكيل - arabo" lang="ar" hreflang="ar" data-title="هاليد الألكيل" 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/Haloalcano" title="Haloalcano - asturiano" lang="ast" hreflang="ast" data-title="Haloalcano" data-language-autonym="Asturianu" data-language-local-name="asturiano" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A5%D0%B0%D0%BB%D0%BE%D0%B0%D0%BB%D0%BA%D0%B0%D0%BD" title="Халоалкан - bulgaro" lang="bg" hreflang="bg" data-title="Халоалкан" data-language-autonym="Български" data-language-local-name="bulgaro" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Haloalc%C3%A0" title="Haloalcà - catalano" lang="ca" hreflang="ca" data-title="Haloalcà" data-language-autonym="Català" data-language-local-name="catalano" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Halogenalkany" title="Halogenalkany - ceco" lang="cs" hreflang="cs" data-title="Halogenalkany" 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/Halogenoalcan" title="Halogenoalcan - gallese" lang="cy" hreflang="cy" data-title="Halogenoalcan" 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/Alkylhalid" title="Alkylhalid - danese" lang="da" hreflang="da" data-title="Alkylhalid" data-language-autonym="Dansk" data-language-local-name="danese" class="interlanguage-link-target"><span>Dansk</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%CF%85%CE%BB%CE%B1%CE%BB%CE%BF%CE%B3%CE%BF%CE%BD%CE%AF%CE%B4%CE%B9%CE%B1" title="Αλκυλαλογονίδια - greco" lang="el" hreflang="el" data-title="Αλκυλαλογονίδια" 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/Haloalkane" title="Haloalkane - inglese" lang="en" hreflang="en" data-title="Haloalkane" data-language-autonym="English" data-language-local-name="inglese" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Haloalcano" title="Haloalcano - spagnolo" lang="es" hreflang="es" data-title="Haloalcano" 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%BClhaliidid" title="Alküülhaliidid - estone" lang="et" hreflang="et" data-title="Alküülhaliidid" 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/Haloalkano" title="Haloalkano - basco" lang="eu" hreflang="eu" data-title="Haloalkano" 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/%D9%87%D8%A7%D9%84%D9%88%D8%A2%D9%84%DA%A9%D8%A7%D9%86" title="هالوآلکان - persiano" lang="fa" hreflang="fa" data-title="هالوآلکان" 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/Alkyylihalidit" title="Alkyylihalidit - finlandese" lang="fi" hreflang="fi" data-title="Alkyylihalidit" 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/Halog%C3%A9noalcane" title="Halogénoalcane - francese" lang="fr" hreflang="fr" data-title="Halogénoalcane" 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/Halaigionalc%C3%A1n" title="Halaigionalcán - irlandese" lang="ga" hreflang="ga" data-title="Halaigionalcán" 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/Haloalcano" title="Haloalcano - galiziano" lang="gl" hreflang="gl" data-title="Haloalcano" 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%94%D7%9C%D7%95%D7%90%D7%9C%D7%A7%D7%90%D7%9F" title="הלואלקאן - ebraico" lang="he" hreflang="he" data-title="הלואלקאן" 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%B9%E0%A5%88%E0%A4%B2%E0%A5%8B%E0%A4%8F%E0%A4%B2%E0%A5%8D%E0%A4%95%E0%A5%87%E0%A4%A8" title="हैलोएल्केन - hindi" lang="hi" hreflang="hi" data-title="हैलोएल्केन" data-language-autonym="हिन्दी" data-language-local-name="hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Haloalkana" title="Haloalkana - indonesiano" lang="id" hreflang="id" data-title="Haloalkana" 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%83%8F%E3%83%AD%E3%82%B2%E3%83%B3%E5%8C%96%E3%82%A2%E3%83%AB%E3%82%AD%E3%83%AB" title="ハロゲン化アルキル - giapponese" lang="ja" hreflang="ja" data-title="ハロゲン化アルキル" 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-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%B0%E1%83%90%E1%83%9A%E1%83%9D%E1%83%92%E1%83%94%E1%83%9C%E1%83%90%E1%83%9A%E1%83%99%E1%83%90%E1%83%9C%E1%83%94%E1%83%91%E1%83%98" title="ჰალოგენალკანები - georgiano" lang="ka" hreflang="ka" data-title="ჰალოგენალკანები" data-language-autonym="ქართული" data-language-local-name="georgiano" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%95%A0%EB%A1%9C%EC%95%8C%EC%BC%80%EC%9D%B8" title="할로알케인 - coreano" lang="ko" hreflang="ko" data-title="할로알케인" data-language-autonym="한국어" data-language-local-name="coreano" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Alkilhalidai" title="Alkilhalidai - lituano" lang="lt" hreflang="lt" data-title="Alkilhalidai" 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/Halog%C4%93nog%C4%BC%C5%ABde%C5%86ra%C5%BEi" title="Halogēnogļūdeņraži - lettone" lang="lv" hreflang="lv" data-title="Halogēnogļūdeņraži" 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%A5%D0%B0%D0%BB%D0%BE%D0%B0%D0%BB%D0%BA%D0%B0%D0%BD" title="Халоалкан - macedone" lang="mk" hreflang="mk" data-title="Халоалкан" data-language-autonym="Македонски" data-language-local-name="macedone" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Haloalkana" title="Haloalkana - malese" lang="ms" hreflang="ms" data-title="Haloalkana" 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/Halogeenalkaan" title="Halogeenalkaan - olandese" lang="nl" hreflang="nl" data-title="Halogeenalkaan" data-language-autonym="Nederlands" data-language-local-name="olandese" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Hydroklorfluorkarbon" title="Hydroklorfluorkarbon - norvegese bokmål" lang="nb" hreflang="nb" data-title="Hydroklorfluorkarbon" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Halogenki_alkilowe" title="Halogenki alkilowe - polacco" lang="pl" hreflang="pl" data-title="Halogenki alkilowe" data-language-autonym="Polski" data-language-local-name="polacco" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%DB%81%DB%8C%D9%84%D9%88%D8%A7%D9%84%DA%A9%DB%8C%D9%86" title="ہیلوالکین - Western Punjabi" lang="pnb" hreflang="pnb" data-title="ہیلوالکین" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Haloalcano" title="Haloalcano - portoghese" lang="pt" hreflang="pt" data-title="Haloalcano" 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/Compu%C8%99i_halogena%C8%9Bi" title="Compuși halogenați - rumeno" lang="ro" hreflang="ro" data-title="Compuși halogenați" data-language-autonym="Română" data-language-local-name="rumeno" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%93%D0%B0%D0%BB%D0%BE%D0%B3%D0%B5%D0%BD%D0%B0%D0%BB%D0%BA%D0%B0%D0%BD%D1%8B" title="Галогеналканы - russo" lang="ru" hreflang="ru" data-title="Галогеналканы" data-language-autonym="Русский" data-language-local-name="russo" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Haloalkan" title="Haloalkan - serbo-croato" lang="sh" hreflang="sh" data-title="Haloalkan" 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-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Haloalkane" title="Haloalkane - Simple English" lang="en-simple" hreflang="en-simple" data-title="Haloalkane" 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-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Haloalkan" title="Haloalkan - serbo" lang="sr" hreflang="sr" data-title="Haloalkan" 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-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Halogenalkan" title="Halogenalkan - svedese" lang="sv" hreflang="sv" data-title="Halogenalkan" 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%8B%E0%AE%85%E0%AE%B2%E0%AF%8D%E0%AE%95%E0%AF%87%E0%AE%A9%E0%AF%8D" title="ஆலோஅல்கேன் - tamil" lang="ta" hreflang="ta" data-title="ஆலோஅல்கேன்" data-language-autonym="தமிழ்" data-language-local-name="tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Haloalkan" title="Haloalkan - turco" lang="tr" hreflang="tr" data-title="Haloalkan" data-language-autonym="Türkçe" data-language-local-name="turco" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%93%D0%B0%D0%BB%D0%BE%D0%B3%D0%B5%D0%BD%D0%BE%D0%B0%D0%BB%D0%BA%D0%B0%D0%BD%D0%B8" title="Галогеноалкани - ucraino" lang="uk" hreflang="uk" data-title="Галогеноалкани" 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/%DB%81%DB%8C%D9%84%D9%88_%D8%A7%D9%84%DA%A9%DB%8C%D9%86" title="ہیلو الکین - urdu" lang="ur" hreflang="ur" data-title="ہیلو الکین" data-language-autonym="اردو" data-language-local-name="urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Haloalkan" title="Haloalkan - vietnamita" lang="vi" 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</nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">Da Wikipedia, l'enciclopedia libera.</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="it" dir="ltr"><p>Gli <b>alogenuri alchilici</b> o <b>alogenuri di alchile</b><sup id="cite_ref-:0_1-0" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> sono dei <a href="/wiki/Composti_organici" class="mw-redirect" title="Composti organici">composti organici</a> saturi derivati dagli alcani per sostituzione di un atomo di <a href="/wiki/Idrogeno" title="Idrogeno">idrogeno</a> con un atomo di <a href="/wiki/Alogeni" title="Alogeni">alogeno</a>, aventi <a href="/wiki/Formula_chimica" title="Formula chimica">formula chimica</a> generale C<sub>n</sub>H<sub>2n+1</sub>−X ( X = <a href="/wiki/Fluoro" title="Fluoro">fluoro</a>, <a href="/wiki/Cloro" title="Cloro">cloro</a>, <a href="/wiki/Bromo" title="Bromo">bromo</a> e <a href="/wiki/Iodio" title="Iodio">iodio</a>),<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> in accordo alla definizione di <a href="/wiki/Alchile" title="Alchile">alchile</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Sono parte della classe più ampia degli alogenoalcani (o aloalcani), nei quali più atomi di idrogeno sono sostituiti da altrettanti atomi di alogeno, uguali o diversi.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Altre classi analoghe agli alogenuri alchilici sono quelle affini degli alogenuri cicloalchilici (dai <a href="/wiki/Cicloalcani" title="Cicloalcani">cicloalcani</a>);<sup id="cite_ref-:0_1-1" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> ci sono poi quelle analoghe che derivano da idrocarburi insaturi: alogenuri alchenilici (dagli <a href="/wiki/Alcheni" title="Alcheni">alcheni</a>), alchinilici (dagli <a href="/wiki/Alchini" title="Alchini">alchini</a>) e quelle importanti degli <a href="/wiki/Alogenuri_arilici" title="Alogenuri arilici">alogenuri arilici</a>, derivati allo stesso modo da <a href="/wiki/Idrocarburi_aromatici" title="Idrocarburi aromatici">idrocarburi aromatici</a>.<b><sup id="cite_ref-:0_1-2" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></b> </p><p>Gli alogenuri di alchile possono essere visti, all'inverso, anche come <a href="/wiki/Acidi_alogenidrici" class="mw-redirect" title="Acidi alogenidrici">acidi alogenidrici</a> in cui l'idrogeno acido è stato sostituito da un <a href="/wiki/Alchile" title="Alchile">alchile</a>, con le importanti conseguenze che ne derivano; il <a href="/wiki/Cloruro_di_metile" class="mw-redirect" title="Cloruro di metile">cloruro di metile</a> CH<sub>3</sub>−Cl, rispetto all'<a href="/wiki/Acido_cloridrico" title="Acido cloridrico">acido cloridrico</a> da cui deriva, ad esempio, non è più una molecola <a href="/wiki/Acido" title="Acido">acida</a> e non è più una molecola protica, capace cioè di donare un <a href="/wiki/Legame_a_idrogeno" title="Legame a idrogeno">legame idrogeno</a>, mentre conserva la qualità di molecola <a href="/wiki/Polarit%C3%A0" title="Polarità">polare</a>: il suo <a href="/wiki/Momento_dipolare" class="mw-redirect" title="Momento dipolare">momento dipolare</a> è μ = 1,86 <a href="/wiki/Debye" title="Debye">D</a>,<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> praticamente uguale a quello di H<sub>2</sub>O; in questo senso sono simili agli <a href="/wiki/Esteri" title="Esteri">esteri</a> nei confronti degli <a href="/wiki/Acidi_carbossilici" title="Acidi carbossilici">acidi carbossilici</a> o anche <a href="/wiki/Acidi_solfonici" title="Acidi solfonici">solfonici</a> da cui derivano. </p><p>Gli alogenuri alchilici sono utili in generale nella <a href="/wiki/Sintesi_organica" title="Sintesi organica">sintesi organica</a> e spesso anche come solventi. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Suddivisioni">Suddivisioni</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alogenuri_alchilici&veaction=edit&section=1" title="Modifica la sezione Suddivisioni" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alogenuri_alchilici&action=edit&section=1" title="Edit section's source code: Suddivisioni"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Gli alogenuri di alchile, come accade per gli alcoli, possono essere ulteriormente divisi quattro tipi: metilici (CH<sub>3</sub>−X), primari (RCH<sub>2</sub>−X), secondari (RR'CH−X) e terziari (RR'R''C−X).<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> In questi lo <a href="/wiki/Stato_di_ossidazione" title="Stato di ossidazione">stato di ossidazione</a> dell'atomo di carbonio unito all'alogeno è diverso ed è, rispettivamente, -2, -1, 0 e +1. Varia anche l'<a href="/wiki/Ingombro_sterico" title="Ingombro sterico">ingombro sterico</a> sullo stesso carbonio, che cresce nella stessa sequenza.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Questa suddivisione è importante perché condiziona, seppure a grandi linee, la loro reattività. </p> <div class="mw-heading mw-heading2"><h2 id="Reattività_generale"><span id="Reattivit.C3.A0_generale"></span>Reattività generale</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alogenuri_alchilici&veaction=edit&section=2" title="Modifica la sezione Reattività generale" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alogenuri_alchilici&action=edit&section=2" title="Edit section's source code: Reattività generale"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>La stabilità del <a href="/wiki/Carbocatione" title="Carbocatione">carbocatione</a> che si forma per <a href="/wiki/Scissione_eterolitica" class="mw-redirect" title="Scissione eterolitica">rottura eterolitica</a> del legame C−X aumenta nella stessa sequenza, sia per <a href="/wiki/Effetto_induttivo" title="Effetto induttivo">effetto induttivo</a> +<i>I</i> degli alchili legati a tale carbonio, sia per <a href="/wiki/Iperconiugazione" title="Iperconiugazione">effetto iperconiugativo</a>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> La combinazione di effetti sterici ed elettronici condiziona il tipo delle <a href="/wiki/Sostituzione_nucleofila_alifatica" title="Sostituzione nucleofila alifatica">sostituzioni nucleofile</a>: a parità di altri fattori, le S<sub>N</sub>1 risultano massimamente favorite per gli alogenuri alchilici terziari, mentre le S<sub>N</sub>2 per quelli metilici.<sup id="cite_ref-:022_9-0" class="reference"><a href="#cite_note-:022-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Inoltre, la facilità con la quale entrambe possono avvenire dipende anche dalla natura dell'alogeno in R−X e aumenta, a parità di altri fattori, dalla <a href="/wiki/Polarizzabilit%C3%A0" title="Polarizzabilità">polarizzabilità</a> di X, e inversamente dall'<a href="/wiki/Energia_di_legame" title="Energia di legame">energia di legame</a> C−X e dalla basicità dell'anione X<sup>−</sup>: I > Br > Cl >> F.<sup id="cite_ref-:02_10-0" class="reference"><a href="#cite_note-:02-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>Nelle <a href="/wiki/Reazione_di_eliminazione" title="Reazione di eliminazione">reazioni di eliminazione</a> (E1 e E2), con le quali si ottengono alcheni, sempre a parità di altri fattori e in particolare della forza della <a href="/wiki/Base_(chimica)" title="Base (chimica)">base</a> e della temperatura, sono favoriti gli alogenuri terziari per entrambi i tipi, ma una base debole favorisce la E1 rispetto alla E2,<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> per la quale la base partecipa direttamente allo <a href="/wiki/Stato_di_transizione" title="Stato di transizione">stato di transizione</a> del <a href="/wiki/Meccanismo_di_reazione" title="Meccanismo di reazione">meccanismo di reazione</a>.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>Gli alogenuri alchilici sono le molecole da cui si parte per preparare i <a href="/wiki/Reattivi_di_Grignard" title="Reattivi di Grignard">reattivi di Grignard</a> (alogenuri di alchil-magnesio): </p><p>R−X + Mg   →   R−Mg−X </p><p>Altrettanto per la preparazione dei <a href="/wiki/Reattivi_di_organo-litio" title="Reattivi di organo-litio">reattivi organolitio</a> (o di alchil-litio): </p><p>R−X + Li   →   R−Li </p><p>Sono composti utili in generale nella <a href="/wiki/Sintesi_organica" title="Sintesi organica">sintesi organica</a> e spesso anche come solventi. </p> <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=Alogenuri_alchilici&veaction=edit&section=3" 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=Alogenuri_alchilici&action=edit&section=3" title="Edit section'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 alogenuri alchilici segue regole simili a quella degli <a href="/wiki/Alcani" title="Alcani">alcani</a>. Gli atomi di alogeno sono considerati come gruppi sostituenti. </p> <dl><dd>CH<sub>3</sub>-CH<sub>2</sub>-CH<sub>2</sub>−Br: <a href="/wiki/1-bromopropano" title="1-bromopropano">1-bromopropano</a></dd></dl> <dl><dd>CH<sub>3</sub></dd> <dd>|</dd> <dd>CH<sub>3</sub>-C−Cl: <a href="/w/index.php?title=2-cloro-2-metilpropano&action=edit&redlink=1" class="new" title="2-cloro-2-metilpropano (la pagina non esiste)">2-cloro-2-metilpropano</a> (cloruro di <i>t</i>-butile)</dd> <dd>|</dd> <dd>CH<sub>3</sub></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Reazione_con_metalli">Reazione con metalli</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alogenuri_alchilici&veaction=edit&section=4" title="Modifica la sezione Reazione con metalli" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alogenuri_alchilici&action=edit&section=4" title="Edit section's source code: Reazione con metalli"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Gli alogenuri alchilici sono di grandissima utilità nella sintesi organica e uno dei loro usi nel laboratorio chimico è quello della reazione con metalli per portare a composti organometallici, soprattutto del litio e del magnesio (ad esempio i <a href="/wiki/Reattivi_di_Grignard" title="Reattivi di Grignard">reattivi di Grignard</a>). </p><p>La reazione è normalmente effettuata trattando <a href="/wiki/Magnesio" title="Magnesio">magnesio</a> o <a href="/wiki/Litio" title="Litio">litio</a> metallici con una soluzione <a href="/wiki/Etere_etilico" class="mw-redirect" title="Etere etilico">eterea</a> dell'alogenuro alchilico. </p> <dl><dd><code>CH<sub>3</sub>CH<sub>2</sub>Cl + Mg (etere) -------> CH<sub>3</sub>CH<sub>2</sub>MgCl </code></dd></dl> <p>Questa è una reazione eterogenea, avviene quindi sull'interfaccia tra fase solida (magnesio, litio) e liquida (soluzione dell'alogenuro in etere). </p><p>Nella preparazione dei reattivi di Grignard, ad esempio, si utilizza magnesio in polvere o limatura. Per la reazione si possono usare bromuri, ioduri e cloruri; tuttavia si utilizzano generalmente i bromuri per l'alto costo degli ioduri e per la bassa reattività dei cloruri. </p><p>La reazione è fortemente esotermica e deve essere condotta in condizioni anidre, per evitare la reazione tra reattivo e acqua, che consuma il reattivo convertendolo nel corrispondente <a href="/wiki/Alcani" title="Alcani">alcano</a>: </p> <dl><dd><code>CH<sub>3</sub>CH<sub>2</sub>MgBr + H<sub>2</sub>O ------> CH<sub>3</sub>CH<sub>3</sub> + HOMgBr </code></dd></dl> <p>I reattivi di organolitio si preparano allo stesso modo utilizzando litio al posto del magnesio. </p> <div class="mw-heading mw-heading2"><h2 id="Preparazioni">Preparazioni</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alogenuri_alchilici&veaction=edit&section=5" title="Modifica la sezione Preparazioni" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Alogenuri_alchilici&action=edit&section=5" title="Edit section's source code: Preparazioni"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Gli alogenuri alchilici si possono ottenere da: </p> <ul><li><a href="/wiki/Alcheni" title="Alcheni">alcheni</a> e <a href="/wiki/Alchini" title="Alchini">alchini</a> per addizione di un idracido HX; l'attacco elettrofilo dell'idrogeno è seguito dall'attacco dell'alogeno;</li> <li><a href="/wiki/Alcoli" title="Alcoli">alcoli</a> per reazione con SOCl<sub>2</sub>; il <a href="/wiki/Cloruro_di_tionile" title="Cloruro di tionile">cloruro di tionile</a> agisce come disidratante promuovendo un attacco nucleofilo intramolecolare del cloro portando complessivamente alla formazione dell'alogenuro alchilico e alla liberazione di SO<sub>2</sub> gassosa;</li> <li><a href="/wiki/Alcani" title="Alcani">alcani</a>, in questo caso le reazioni sono meno generalizzabili, anche a causa di una certa componente <a href="/wiki/Regioselettivit%C3%A0" title="Regioselettività">regioselettiva</a>, ma in genere si fanno reagire a caldo un <a href="/wiki/Alcano" class="mw-redirect" title="Alcano">alcano</a> e un <a href="/wiki/Alogeno" class="mw-redirect" title="Alogeno">alogeno</a> e si ottiene un alogenuro più un <a href="/wiki/Idracido" title="Idracido">idracido</a> H-X.</li></ul> <p>Infine si possono ottenere alogenuri arilici mediante <a href="/wiki/Sostituzione_elettrofila_aromatica" title="Sostituzione elettrofila aromatica">sostituzione elettrofila</a> da <a href="/wiki/Idrocarburi_aromatici" title="Idrocarburi aromatici">idrocarburi aromatici</a>. </p> <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=Alogenuri_alchilici&veaction=edit&section=6" 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=Alogenuri_alchilici&action=edit&section=6" title="Edit section's source code: Note"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-:0-1"><span class="mw-cite-backlink"><b>^</b> <sup><i><a href="#cite_ref-:0_1-0">a</a></i></sup> <sup><i><a href="#cite_ref-:0_1-1">b</a></i></sup> <sup><i><a href="#cite_ref-:0_1-2">c</a></i></sup></span> <span class="reference-text"><cite class="citation libro" style="font-style:normal"> R. Fusco, G. Bianchetti e V. Rosnati, <span style="font-style:italic;">CHIMICA ORGANICA</span>, volume primo, L. G. Guadagni, 1974, p. 33.</cite></span> </li> <li id="cite_note-2"><a href="#cite_ref-2"><b>^</b></a> <span class="reference-text"><cite class="citation libro" style="font-style:normal"> William Henry Brown, Brent L. Iverson e Eric V. Anslyn, <span style="font-style:italic;">Organic chemistry</span>, Eighth edition, Cengage Learning, 2018, p. 330, <a href="/wiki/ISBN" title="ISBN">ISBN</a> <a href="/wiki/Speciale:RicercaISBN/978-1-305-58035-0" title="Speciale:RicercaISBN/978-1-305-58035-0">978-1-305-58035-0</a>.</cite></span> </li> <li id="cite_note-3"><a href="#cite_ref-3"><b>^</b></a> <span class="reference-text"><cite class="citation web" style="font-style:normal"> The International Union of Pure and Applied Chemistry (IUPAC), <a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/A00228"><span style="font-style:italic;">IUPAC - alkyl groups (A00228)</span></a>, su <span style="font-style:italic;">goldbook.iupac.org</span>. <small>URL consultato l'11 ottobre 2024</small>.</cite></span> </li> <li id="cite_note-4"><a href="#cite_ref-4"><b>^</b></a> <span class="reference-text"><cite class="citation libro" 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://onlinelibrary.wiley.com/doi/book/10.1002/9780470771280"><span style="font-style:italic;">The Carbon—Halogen Bond (1973)</span></a>, collana <span style="font-style:italic;">PATAI'S Chemistry of Functional Groups</span>, 1ª ed., Wiley, 1973-01, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1002%2F9780470771280">10.1002/9780470771280</a>, <a href="/wiki/ISBN" title="ISBN">ISBN</a> <a href="/wiki/Speciale:RicercaISBN/978-0-471-66943-2" title="Speciale:RicercaISBN/978-0-471-66943-2">978-0-471-66943-2</a>. <small>URL consultato il 12 ottobre 2024</small>.</cite></span> </li> <li id="cite_note-5"><a href="#cite_ref-5"><b>^</b></a> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal">(<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>) G. Wlodarczak, F. Herlemont e J. Demaison, <a rel="nofollow" class="external text" href="https://www.sciencedirect.com/science/article/pii/0022285285901717"><span style="font-style:italic;">Combined subdoppler laser-Stark and millimeter-wave spectroscopies: Analysis of the ν6 band of CH335Cl</span></a>, in <span style="font-style:italic;">Journal of Molecular Spectroscopy</span>, vol. 112, n. 2, 1º agosto 1985, pp. 401–412, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1016%2F0022-2852%2885%2990171-7">10.1016/0022-2852(85)90171-7</a>. <small>URL consultato il 2 agosto 2022</small>.</cite></span> </li> <li id="cite_note-6"><a href="#cite_ref-6"><b>^</b></a> <span class="reference-text"><cite class="citation libro" style="font-style:normal"> John McMurry, <span style="font-style:italic;">Organic chemistry</span>, 8e, Brooks/Cole, Cengage Learning, 2012, p. 244, <a href="/wiki/ISBN" title="ISBN">ISBN</a> <a href="/wiki/Speciale:RicercaISBN/978-0-8400-5444-9" title="Speciale:RicercaISBN/978-0-8400-5444-9">978-0-8400-5444-9</a>.</cite></span> </li> <li id="cite_note-7"><a href="#cite_ref-7"><b>^</b></a> <span class="reference-text"><cite class="citation libro" style="font-style:normal"> Michael Smith e Jerry March, <span style="font-style:italic;">March's advanced organic chemistry: reactions, mechanisms, and structure</span>, Eighth edition, John Wiley, 2020, pp. 377-378, <a href="/wiki/ISBN" title="ISBN">ISBN</a> <a href="/wiki/Speciale:RicercaISBN/978-1-119-37179-3" title="Speciale:RicercaISBN/978-1-119-37179-3">978-1-119-37179-3</a>.</cite></span> </li> <li id="cite_note-8"><a href="#cite_ref-8"><b>^</b></a> <span class="reference-text"><cite class="citation libro" style="font-style:normal"> Francis A. Carey e Richard J. Sundberg, <span style="font-style:italic;">Advanced organic chemistry</span>, 5th ed, Springer, 2007, pp. 300-301, <a href="/wiki/ISBN" title="ISBN">ISBN</a> <a href="/wiki/Speciale:RicercaISBN/978-0-387-44897-8" title="Speciale:RicercaISBN/978-0-387-44897-8">978-0-387-44897-8</a>.</cite></span> </li> <li id="cite_note-:022-9"><a href="#cite_ref-:022_9-0"><b>^</b></a> <span class="reference-text"><cite class="citation libro" style="font-style:normal"> R.O.C. Norman, <span style="font-style:italic;">CHIMICA ORGANICA Principi e Applicazioni alla Sintesi</span>, traduzione di Paolo Da Re, Piccin, 1973, p. 128.</cite></span> </li> <li id="cite_note-:02-10"><a href="#cite_ref-:02_10-0"><b>^</b></a> <span class="reference-text"><cite class="citation libro" style="font-style:normal"> R.O.C. Norman, <span style="font-style:italic;">CHIMICA ORGANICA Principi e Applicazioni alla Sintesi</span>, traduzione di Paolo Da Re, Piccin, 1973, p. 126.</cite></span> </li> <li id="cite_note-11"><a href="#cite_ref-11"><b>^</b></a> <span class="reference-text"><cite class="citation libro" style="font-style:normal"> Michael Smith e Jerry March, <span style="font-style:italic;">March's advanced organic chemistry: reactions, mechanisms, and structure</span>, Eighth edition, John Wiley, 2020, p. 1280, <a href="/wiki/ISBN" title="ISBN">ISBN</a> <a href="/wiki/Speciale:RicercaISBN/978-1-119-37179-3" title="Speciale:RicercaISBN/978-1-119-37179-3">978-1-119-37179-3</a>.</cite></span> </li> <li id="cite_note-12"><a href="#cite_ref-12"><b>^</b></a> <span class="reference-text"><cite class="citation libro" style="font-style:normal"> Francis A. Carey e Richard J. Sundberg, <span style="font-style:italic;">Advanced organic chemistry</span>, 5th ed, Springer, 2007, p. 552, <a href="/wiki/ISBN" title="ISBN">ISBN</a> <a href="/wiki/Speciale:RicercaISBN/978-0-387-44897-8" title="Speciale:RicercaISBN/978-0-387-44897-8">978-0-387-44897-8</a>.</cite></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=Alogenuri_alchilici&veaction=edit&section=7" 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=Alogenuri_alchilici&action=edit&section=7" title="Edit section'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 ed., Bologna, Zanichelli, 2001, p. 53, <a href="/wiki/ISBN" title="ISBN">ISBN</a> <a href="/wiki/Speciale:RicercaISBN/88-08-09414-6" title="Speciale:RicercaISBN/88-08-09414-6">88-08-09414-6</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=Alogenuri_alchilici&veaction=edit&section=8" 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=Alogenuri_alchilici&action=edit&section=8" title="Edit section's source code: Voci correlate"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Alogenuri_arilici" title="Alogenuri arilici">Alogenuri arilici</a></li> <li><a href="/wiki/Iodometano" title="Iodometano">Iodometano</a></li> <li><a href="/wiki/1-clorobutano" title="1-clorobutano">1-clorobutano</a></li> <li><a href="/wiki/2-bromopropano" title="2-bromopropano">2-bromopropano</a></li> <li><a href="/wiki/1-bromopropano" title="1-bromopropano">1-bromopropano</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=Alogenuri_alchilici&veaction=edit&section=9" 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=Alogenuri_alchilici&action=edit&section=9" title="Edit section'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=""><span class="plainlinks" title="commons:Category:Haloalkanes"><a class="external text" href="https://commons.wikimedia.org/wiki/Category:Haloalkanes?uselang=it">Wikimedia Commons</a></span></li></ul></div> <ul><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:Haloalkanes?uselang=it">alogenuri alchilici</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=Alogenuri_alchilici&veaction=edit&section=10" 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=Alogenuri_alchilici&action=edit&section=10" title="Edit section'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; 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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" 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href="/w/index.php?title=Silanoli&action=edit&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&action=edit&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-Inquinamento"><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:Inquinamento" title="Template:Inquinamento"><span title="Vai alla pagina del template">V</span></a> · <a href="/wiki/Discussioni_template:Inquinamento" title="Discussioni template:Inquinamento"><span title="Discuti del template">D</span></a> · <a class="external text" href="https://it.wikipedia.org/w/index.php?title=Template:Inquinamento&action=edit"><span title="Modifica il template. 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