{"id":48601,"date":"2023-09-25T22:00:43","date_gmt":"2023-09-25T16:15:43","guid":{"rendered":"https:\/\/thechemistrynotes.com\/?p=48601"},"modified":"2023-09-25T22:00:48","modified_gmt":"2023-09-25T16:15:48","slug":"chugaev-reaction-mechanism-application","status":"publish","type":"post","link":"https:\/\/thechemistrynotes.com\/chugaev-reaction-mechanism-application\/","title":{"rendered":"Chugaev Reaction: Mechanism, Applications, Limitations"},"content":{"rendered":"\n<figure class=\"wp-block-image size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"1205\" height=\"631\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Chugaev-reaction.jpg\" alt=\"Chugaev reaction\" class=\"wp-image-48605\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Chugaev-reaction.jpg 1205w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Chugaev-reaction-300x157.jpg 300w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Chugaev-reaction-1024x536.jpg 1024w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Chugaev-reaction-768x402.jpg 768w\" sizes=\"(max-width: 1205px) 100vw, 1205px\" \/><\/figure>\n\n\n\n<p>Chugaev reaction is a chemical process that eliminates water from an alcohol, resulting in the formation of an <a href=\"https:\/\/thechemistrynotes.com\/alkenes\/\">alkene<\/a>. Xanthate is the intermediate. It is named after Russian chemist Lev Aleksandrovich Chugayev, who described the reaction sequence for the first time in 1899.<\/p>\n\n\n\n<p>In the first stage, an alkoxide and carbon disulfide (CS2) are combined to generate a xanthate salt. Iodomethane is used to convert the alkoxide to methyl xanthate. Alkenes are generated by intramolecular elimination at around 200 \u00b0C. A hydrogen atom is transferred from a carbon atom to xanthate oxygen in syn elimination in the transition state of the 6-membered ring.<\/p>\n\n\n\n<div id=\"ez-toc-container\" class=\"ez-toc-v2_0_63 counter-hierarchy ez-toc-counter ez-toc-custom ez-toc-container-direction\">\n<div class=\"ez-toc-title-container\">\n<p class=\"ez-toc-title \" >Table of Contents<\/p>\n<span class=\"ez-toc-title-toggle\"><a href=\"#\" class=\"ez-toc-pull-right ez-toc-btn ez-toc-btn-xs ez-toc-btn-default ez-toc-toggle\" aria-label=\"Toggle Table of Content\"><span class=\"ez-toc-js-icon-con\"><span class=\"\"><span class=\"eztoc-hide\" style=\"display:none;\">Toggle<\/span><span class=\"ez-toc-icon-toggle-span\"><svg style=\"fill: #0a0a0a;color:#0a0a0a\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" class=\"list-377408\" width=\"20px\" height=\"20px\" viewBox=\"0 0 24 24\" fill=\"none\"><path d=\"M6 6H4v2h2V6zm14 0H8v2h12V6zM4 11h2v2H4v-2zm16 0H8v2h12v-2zM4 16h2v2H4v-2zm16 0H8v2h12v-2z\" fill=\"currentColor\"><\/path><\/svg><svg style=\"fill: #0a0a0a;color:#0a0a0a\" class=\"arrow-unsorted-368013\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" width=\"10px\" height=\"10px\" viewBox=\"0 0 24 24\" version=\"1.2\" baseProfile=\"tiny\"><path d=\"M18.2 9.3l-6.2-6.3-6.2 6.3c-.2.2-.3.4-.3.7s.1.5.3.7c.2.2.4.3.7.3h11c.3 0 .5-.1.7-.3.2-.2.3-.5.3-.7s-.1-.5-.3-.7zM5.8 14.7l6.2 6.3 6.2-6.3c.2-.2.3-.5.3-.7s-.1-.5-.3-.7c-.2-.2-.4-.3-.7-.3h-11c-.3 0-.5.1-.7.3-.2.2-.3.5-.3.7s.1.5.3.7z\"\/><\/svg><\/span><\/span><\/span><\/a><\/span><\/div>\n<nav><ul class='ez-toc-list ez-toc-list-level-1 ' ><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-1\" href=\"https:\/\/thechemistrynotes.com\/chugaev-reaction-mechanism-application\/#what-is-chugaevs-reaction\" title=\"What is Chugaev&#8217;s reaction?\">What is Chugaev&#8217;s reaction?<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-2\" href=\"https:\/\/thechemistrynotes.com\/chugaev-reaction-mechanism-application\/#mechanism-of-chugaev-reaction\" title=\"Mechanism of Chugaev Reaction\">Mechanism of Chugaev Reaction<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-3\" href=\"https:\/\/thechemistrynotes.com\/chugaev-reaction-mechanism-application\/#application-of-chugaev-reaction\" title=\"Application of Chugaev Reaction\">Application of Chugaev Reaction<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-4\" href=\"https:\/\/thechemistrynotes.com\/chugaev-reaction-mechanism-application\/#limitations-of-chugaev-reaction\" title=\"Limitations of Chugaev Reaction\">Limitations of Chugaev Reaction<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-5\" href=\"https:\/\/thechemistrynotes.com\/chugaev-reaction-mechanism-application\/#references\" title=\"References\">References<\/a><\/li><\/ul><\/nav><\/div>\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"what-is-chugaevs-reaction\"><\/span><strong>What is Chugaev&#8217;s reaction?<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<p>The Chugaev reaction mechanism is a concerted procedure. In this process, sodium xanthate is formed by the reaction of <a href=\"https:\/\/thechemistrynotes.com\/alcohols\/\">alcohol<\/a> with carbon disulfide in the presence of sodium hydroxide. Sodium xanthate is then alkylated with methyl iodide to form xanthate ester. When pyrolyzed, this xanthate yields olefin or alkene. Thus, the Chugaev reaction converts\u00a0alcohol into olefin via the equivalent xanthate esters. This is also known as the Chugaev elimination\u00a0or the Chugaev xanthate reaction.<\/p>\n\n\n<div class=\"wp-block-image\">\n<figure class=\"aligncenter size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"761\" height=\"231\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-72.png\" alt=\"\" class=\"wp-image-48604\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-72.png 761w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-72-300x91.png 300w\" sizes=\"(max-width: 761px) 100vw, 761px\" \/><\/figure><\/div>\n\n\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"mechanism-of-chugaev-reaction\"><\/span><strong>Mechanism of<\/strong> <strong>Chugaev Reaction<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<ol>\n<li>Formation of xanthate ester<\/li>\n<\/ol>\n\n\n<div class=\"wp-block-image\">\n<figure class=\"aligncenter size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"699\" height=\"385\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-70.png\" alt=\"\" class=\"wp-image-48602\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-70.png 699w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-70-300x165.png 300w\" sizes=\"(max-width: 699px) 100vw, 699px\" \/><\/figure><\/div>\n\n\n<p>2.  Pyrolysis process<\/p>\n\n\n<div class=\"wp-block-image\">\n<figure class=\"aligncenter size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"707\" height=\"299\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-71.png\" alt=\"\" class=\"wp-image-48603\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-71.png 707w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-71-300x127.png 300w\" sizes=\"(max-width: 707px) 100vw, 707px\" \/><\/figure><\/div>\n\n\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"application-of-chugaev-reaction\"><\/span><strong>Application of Chugaev Reaction<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<ul>\n<li>This reaction is extremely effective for converting secondary and tertiary alcohols into alkenes.<\/li>\n\n\n\n<li>This reaction can be used to make a variety of olefins such as bornylene, menthene, and others.<\/li>\n<\/ul>\n\n\n\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"limitations-of-chugaev-reaction\"><\/span><strong>Limitations of Chugaev Reaction<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<ul>\n<li>A mixture of isomeric olefins is formed if the Beta-carbon includes more than one hydrogen or if elimination is possible in more than one place.<\/li>\n\n\n\n<li>It is difficult to break down by heating because the xanthate ester of primary alcohol has excellent thermal stability.<\/li>\n<\/ul>\n\n\n\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"references\"><\/span><strong>References<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<ul>\n<li>https:\/\/chemistry-reaction.com\/chugaev-elimination\/.<\/li>\n\n\n\n<li>Wang, Z., Comprehensive Organic Name Reactions and Reagents, John Wiley &amp; Sons, Inc.,2010<\/li>\n\n\n\n<li>Laue T.,Plagens A.,Named Organic Reactions, Second edition, John Wiley &amp; Sons, Ltd, 2005.<\/li>\n\n\n\n<li>https:\/\/academic-accelerator.com\/encyclopedia\/chugaev-elimination<\/li>\n<\/ul>\n","protected":false},"excerpt":{"rendered":"<p>Chugaev reaction is a chemical process that eliminates water from an alcohol, resulting in the formation of an alkene. Xanthate is the intermediate. It is named after Russian chemist Lev &#8230; <a title=\"Chugaev Reaction: Mechanism, Applications, Limitations\" class=\"read-more\" href=\"https:\/\/thechemistrynotes.com\/chugaev-reaction-mechanism-application\/\" aria-label=\"Read more about Chugaev Reaction: Mechanism, Applications, Limitations\">Read more<\/a><\/p>\n","protected":false},"author":4,"featured_media":48605,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[21],"tags":[2910,2908,2911,2909],"_links":{"self":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts\/48601"}],"collection":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/users\/4"}],"replies":[{"embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/comments?post=48601"}],"version-history":[{"count":1,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts\/48601\/revisions"}],"predecessor-version":[{"id":48606,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts\/48601\/revisions\/48606"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/media\/48605"}],"wp:attachment":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/media?parent=48601"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/categories?post=48601"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/tags?post=48601"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}