{"id":8626,"date":"2014-11-14T18:38:03","date_gmt":"2014-11-14T23:38:03","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=8626"},"modified":"2025-08-27T15:00:48","modified_gmt":"2025-08-27T20:00:48","slug":"ether-synthesis-via-alcohols-and-acid","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2014\/11\/14\/ether-synthesis-via-alcohols-and-acid\/","title":{"rendered":"Alcohols To Ethers via Acid Catalysis"},"content":{"rendered":"<p><strong>How To Make Ethers With Alcohols And Acid<\/strong><\/p>\n<ul>\n<li>Symmetrical ethers can be made from the acid-catalyzed dehydration of primary alcohols.<\/li>\n<li>A classic example is the heating of ethanol at 130-140 \u00b0C to give diethyl ether.<\/li>\n<li>The reaction proceeds through protonation of a hydroxyl group to give the conjugate acid followed by an S<sub>N<\/sub>2 reaction to give the symmetrical ether.<\/li>\n<li>The process works best for making symmetrical ethers of primary alcohols.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-35244\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/0-summary-synthesis-of-symmetrical-ethers-through-treatment-of-primary-alcohols-with-acid-1.gif\" alt=\"summary of methods for ether formation from alkenes with strong acid and alcohols or via oxymercuration\" width=\"640\" height=\"333\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Synthesis of Symmetrical Ethers Via Acid-Catalyzed Dehydration of Alcohols<\/a><\/li>\n<li><a href=\"#two\">The Mechanism: Acid-Catalyzed Dehydration of Alcohols<\/a><\/li>\n<li><a href=\"#three\">Summary: Symmetrical Ether Synthesis via Alcohol Dehydration<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quizzes\">Quiz Yourself!<\/a><\/li>\n<li><a href=\"#references\">(Advanced) References and Further Reading<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><a id=\"one\"><\/a>1. Synthesis Of Symmetrical Ethers Via Acid-Catalyzed Dehydration of Alcohols<\/h2>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/11\/07\/synthesis-of-ethers-2-back-to-the-future\/\">Last post<\/a> I got a little ahead of myself. I was all excited about getting into the reactions of ethers, and forgot that there&#8217;s one last method for ether synthesis that we haven&#8217;t covered. It&#8217;s actually not\u00a0<em>that<\/em> general so you can likely skip ahead. But for the sake of completeness, here it is.<\/p>\n<p>Remember when we said that <a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/10\/06\/how-to-make-alcohols-more-reactive\/\">alcohols often\u00a0need a &#8220;kick in the pants&#8221;<\/a> in order to participate in reactions? That is, we either\u00a0add acid to <strong>protonate<\/strong> them\u00a0(forming their conjugate acid, which has a better leaving group) or add base to <strong>deprotonate<\/strong> them (forming their conjugate base, which is a better nucleophile).<\/p>\n<p>Today&#8217;s post is a perfect example. Here&#8217;s the summary.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15150\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-formation-of-ethers-through-acid-catalyzed-dehydration-of-alcohols-eg-ethanol-with-h2so4-at-about-130-deg-celsius-limited-to-symmetrical-ethers.gif\" alt=\"formation of ethers through acid catalyzed dehydration of alcohols eg ethanol with h2so4 at about 130 deg celsius limited to symmetrical ethers\" width=\"600\" height=\"260\" \/><\/p>\n<p>Here&#8217;s the deal. If we take a simple alcohol &#8211; ethanol is a perfect example &#8211; and heat it in the presence of strong acid, an <strong>ether<\/strong> can form.<\/p>\n<p>How does this work?<\/p>\n<h2><strong><a id=\"two\"><\/a>2. Mechanism: Synthesis Of Symmetrical Ethers via Acid-Catalyzed\u00a0 Dehydration of Alcohols<\/strong><\/h2>\n<p>There are three key steps.<\/p>\n<p><strong>First of all,<\/strong> one equivalent of alcohol is protonated to its <strong>conjugate acid<\/strong> \u00a0&#8211; which has the <strong>good leaving group<\/strong>, OH<sub>2<\/sub> \u00a0(water, a weak base). (<span style=\"color: #993366;\"><em>Remember that the conjugate acid is a better leaving group &#8211; see <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/04\/12\/what-makes-a-good-leaving-group\/\">What Makes a Good Leaving Group<\/a><\/em><\/span>).<\/p>\n<p><strong>Next,<\/strong> another equivalent of the alcohol can now perform <strong>nucleophilic attack at carbon (S<sub>N<\/sub>2)<\/strong>, leading to displacement of OH<sub>2<\/sub> (water) and formation of a new C-O bond. \u00a0This is an S<sub>N<\/sub>2 reaction. (See <a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/07\/04\/the-sn2-mechanism\/\"><em>The SN2 Mechanism<\/em><\/a>)<\/p>\n<p><strong>The final step<\/strong> is<strong> deprotonation<\/strong> of the product by another equivalent of solvent (or other weak base), resulting in our ether product.<\/p>\n<p>Here&#8217;s a drawing of the mechanism:<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15151\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-acid-catalyzed-formation-of-symmetrical-ethers-mechanism-curved-arrow-protonation-of-alcohol-sn2-reaction-deprotonation.gif\" alt=\"acid catalyzed formation of symmetrical ethers mechanism curved arrow protonation of alcohol sn2 reaction deprotonation\" width=\"630\" height=\"313\" \/><\/p>\n<h2><strong><a id=\"three\"><\/a>3. Summary: Formation of Symmetrical Ethers From Alcohols<\/strong><\/h2>\n<p>So how important is this process, really?<\/p>\n<p><strong>Industrially<\/strong>, it&#8217;s very important process for the synthesis of diethyl ether, which is a commodity chemical and useful solvent for organic chemistry. Ethanol is cheap. Sulfuric acid is cheap. Heat, distill, and Bob&#8217;s your uncle. \u00a0Over 10 million tons of the stuff is made annually via this process.<\/p>\n<p><strong>Practically<\/strong> &#8211; and I say this to you, undergraduate student of chemistry &#8211; \u00a0from a synthetic perspective &#8211;<strong>it&#8217;s not a very\u00a0<em>general<\/em> synthesis of ethers.<\/strong><\/p>\n<p>First of all, it&#8217;s limited to <em>symmetrical<\/em> ethers. If we try to make unsymmetrical ethers using this process, we will end up with mixtures that will need to be separated, giving us low yields of each individual component.<\/p>\n<p>Secondly, the temperature has to be carefully optimized, because there are lots of side reactions possible. For example the optimal temperature for the formation of diethyl ether is about 130-140 degrees C. Once the temperature gets to 150 degrees and above, elimination starts to compete, leading to the formation of ethylene gas.<\/p>\n<p><em>[<span style=\"color: #993366;\">And this is for primary alcohols, which don&#8217;t form carbocations very easily. Once you get into the category of using this process for secondary and tertiary alcohols, carbocations are much easier to form and elimination becomes an even more significant destructive pathway<\/span>.]<\/em><\/p>\n<p>You should know what the correct answer for the question below. And be able to draw the mechanism. That&#8217;s it.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"41159\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"41159\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"41159\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"41159\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-41159\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-41159 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"41159\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-yxa5q\" data-id=\"yxa5q\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2438-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2438-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>Beyond that, \u00a0unless you&#8217;re Sigma-Aldrich and are planning to make several metric tons of an ether, you can comfortably omit this method of ether synthesis from your synthetic toolbox. The Williamson ether synthesis will do the job just as well, and can also be used to make unsymmetrical ethers to boot.<\/p>\n<p>Okay . Finally, next post we get to write all about the different reactions of ethers. We&#8217;ve learned five (5) &#8211; count &#8217;em &#8211; ways of making ethers, and now that we&#8217;re armed with all this knowledge, we&#8217;ll go out and talk about all the different things we can do!<\/p>\n<p><strong>Next Post &#8211; <a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/11\/19\/ether-cleavage\/\">Cleavage Of Ethers With Acid<\/a><\/strong><\/p>\n<hr \/>\n<h2><a id=\"notes\"><\/a>Notes<\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/11\/19\/ether-cleavage\/\" class=\"\"><span>Cleavage Of Ethers With Acid<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/10\/24\/the-williamson-ether-synthesis\/\" class=\"\"><span>The Williamson Ether Synthesis<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/10\/30\/williamson-ether-synthesis-planning\/\" class=\"\"><span>Williamson Ether Synthesis: Planning<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/\" class=\"\"><span>Epoxides \u2013 The Outlier Of The Ether Family<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/07\/05\/thiols-and-thioethers\/\" class=\"\"><span>Thiols And Thioethers<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/11\/14\/ether-synthesis-via-alcohols-and-acid\/\" class=\"\"><span>Alcohols To Ethers via Acid Catalysis<\/span><\/a><\/li><\/ul><\/div>\n<p><b>Note 1. <\/b>This synthesis of ethers is so practically straightforward that it lends itself to &#8220;How-To&#8221; videos. Don&#8217;t do this unless you know what you&#8217;re doing &#8211; ether is extremely flammable.<\/p>\n<p><iframe src=\"\/\/www.youtube.com\/embed\/ytdO3YzXNkQ\" width=\"560\" height=\"315\" frameborder=\"0\" allowfullscreen=\"allowfullscreen\"><\/iframe><\/p>\n<hr \/>\n<h2><a id=\"quizzes\"><\/a>Quiz Yourself!<\/h2>\n<p>&nbsp;<\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3389-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3390-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3391-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3392-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n<hr \/>\n<h2><a id=\"references\"><\/a>(Advanced) References and Further Reading<\/h2>\n<p>The formation of diethyl ether from ethanol and acid has been known since the days of <a href=\"https:\/\/en.wikipedia.org\/wiki\/Valerius_Cordus\">Valerius Cordus,<\/a> who reported the synthesis in 1540.<\/p>\n<ol>\n<li><strong>Catalysts for forming Diethyl Ether<br \/>\nInventors<\/strong>: Cheng Zhang, Victor J. Johnson<strong><br \/>\nAssignee<\/strong>: Celanese International Corp.<br \/>\n<strong>Publication Date: <\/strong> 18, 2014<strong><br \/>\nPub. No.: <\/strong>US 20140275636A1<br \/>\nThis describes an industrial process for diethyl ether synthesis, which is done using a heterogeneous catalyst.<\/li>\n<li><strong>Single stage synthesis of diisopropyl ether \u2013 an alternative octane enhancer for lead-free petrol<br \/>\n<\/strong>Frank P. Heese, Mark E. Dry, Klaus P. M\u00f6ller<strong><br \/>\n<\/strong><em>Catalysis Today<\/em><strong> 1999<\/strong>, <em>49<\/em> (1-3), 327-335<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/www.sciencedirect.com\/science\/article\/abs\/pii\/S0920586198004404\">10.1016\/S0920-5861(98)00440-4<\/a><br \/>\nThis paper shows that the mechanism for formation of symmetrical ethers from secondary alcohols (e.g. isopropanol) is more complex, as bimolecular dehydration can compete with other pathways (e.g. S<sub>N<\/sub>1 or elimination-addition). Diisopropyl ether is sometimes used as a solvent but requires even more care with handling and storage compared to other ethers, as it is even more prone to formation of explosive peroxides.<\/li>\n<li><strong>Process for Preparing Diisopropyl Ether<br \/>\nInventor: <\/strong>Hanbury John Woods<strong><br \/>\nAssignee: <\/strong>Gulf Oil Canada Limited<strong><br \/>\nPublication Date: <\/strong> 16, 1977<strong><br \/>\nPub. No.: <\/strong>US 4,042,633<br \/>\nA patent on an industrial process for preparing diisopropyl ether from isopropanol. This is also done with a heterogeneous catalyst (Montmorillonite clay in this case).<\/li>\n<li><strong>Reactions of phenols and alcohols over thoria: Mechanism of ether formation<br \/>\n<\/strong> Karuppannasamy, K. Narayanan, C. N. Pillai<strong><br \/>\n<\/strong><em>J. Catalysis<\/em><strong> 1980<\/strong>, <em>66<\/em> (2), 281-289<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/www.sciencedirect.com\/science\/article\/pii\/0021951780900329\">10.1016\/0021-9517(80)90032-9<\/a><br \/>\nUnder forcing conditions, phenol can dehydrate to diphenyl ether, but this proceeds through an unusual mechanism.<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>How To Make Ethers With Alcohols And Acid Symmetrical ethers can be made from the acid-catalyzed dehydration of primary alcohols. A classic example is the <\/p>\n","protected":false},"author":1,"featured_media":35244,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1420],"tags":[167,1034,850,271,352],"post_folder":[],"class_list":["post-8626","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alcohols-epoxides-ethers","tag-alcohols","tag-dehydration","tag-ethers","tag-sn2","tag-synthesis"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Alcohols To Ethers via Acid Catalysis &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"Alcohols can be converted to symmetrical ethers through treatment with an acid catalyst (eg H2SO4) at high temperatures. 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