{"id":8631,"date":"2014-11-19T17:21:14","date_gmt":"2014-11-19T22:21:14","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=8631"},"modified":"2025-09-23T19:44:11","modified_gmt":"2025-09-24T00:44:11","slug":"ether-cleavage","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2014\/11\/19\/ether-cleavage\/","title":{"rendered":"Cleavage Of Ethers With Acid"},"content":{"rendered":"<p><strong>Acidic Cleavage of Ethers Can Proceed Through an S<sub>N<\/sub>2 or S<sub>N<\/sub>1 Mechanism, Depending On The Structure<\/strong><\/p>\n<ul>\n<li>Ethers do not undergo very many reactions.<\/li>\n<li>One key reaction of ethers is that they can undergo cleavage to alcohols in the presence of strong acids, such as HI, or strong Lewis acids such as boron tribromide (BBr<sub>3<\/sub>) .<\/li>\n<li>These reactions involve protonation of the ether oxygen, followed by either an S<sub>N<\/sub>1 or S<sub>N<\/sub>2 reaction pathway, depending on structure (<span style=\"color: #993366;\"><em>ethers of primary alcohols tend to undergo cleavage via S<sub>N<\/sub>2, ethers of tertiary alcohols tend to undergo cleavage via S<sub>N<\/sub>1<\/em><\/span>).<\/li>\n<li>If excess HI is used for the cleavage of alkyl ethers, the products tend to be alkyl iodides.<\/li>\n<li>Because ethers are so unreactive to all but the most acidic conditions, they can find use as protecting groups for alcohols.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-35239\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/08\/0-overview-reactions-of-ethers-with-acid-ether-cleavage-using-strong-acid-hi-leads-to-roh-and-ri.gif\" alt=\"summary of methods for ether formation from alkenes with strong acid and alcohols or via oxymercuration\" width=\"640\" height=\"302\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">All The Reactions Of Ethers In Once Place (har)<\/a><\/li>\n<li><a href=\"#two\">The First Step In Ether Cleavage Is Protonation<\/a><\/li>\n<li><a href=\"#three\">For Methyl and Primary Ethers, The Second Step of Ether Cleavage is S<sub>N<\/sub>2<\/a><\/li>\n<li><a href=\"#four\">For Tertiary Ethers, The Second Step of Ether Cleavage is S<sub>N<\/sub>1<\/a><\/li>\n<li><a href=\"#five\">For Secondary\u00a0 Ethers, The Second Step Could Occur Through a Mixture of Either Pathway<\/a><\/li>\n<li><a href=\"#six\">The Mechanism for Cleavage of Unsymmetrical\u00a0 Ethers Is Hard To Generalize (With One Exception!)<\/a><\/li>\n<li><a href=\"#seven\">Intramolecular Cleavage of Ethers<\/a><\/li>\n<li><a href=\"#eight\">Summary: Acidic Cleavage of Ethers<\/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. All The Reactions of Ethers In One Place (har!)<\/h2>\n<p>I&#8217;ve been looking forward to today&#8217;s post for a long time! We&#8217;ve gone through so many different ways of synthesizing ethers, and finally we get to talk about all the exciting things we get to do with them.<\/p>\n<p>Here it is, the moment you&#8217;ve been waiting for. All the reactions of ethers in one place:<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15153\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-overview-reactions-of-ethers-with-acid-ether-cleavage-using-strong-acid-hi-leads-to-roh-and-ri.gif\" alt=\"overview reactions of ethers with acid ether cleavage using strong acid hi leads to roh and ri\" width=\"640\" height=\"223\" \/><\/p>\n<p>We have now covered the reactions of ethers.<\/p>\n<p>Thank you for your attention.<\/p>\n<p><strong>Is that it?<\/strong> Yes, really: <strong>the only significant reaction of ethers you need to know&#8230;. is how to break them.\u00a0<\/strong><\/p>\n<p><span style=\"color: #993366;\"><em>[I was just pulling your leg about the &#8220;exciting things we get to do with ethers&#8221; line.]<\/em><\/span><\/p>\n<p>Does this\u00a0make ethers the most boring functional group there is? Yes!!! (as long as you don&#8217;t count\u00a0alkanes as a &#8220;functional group&#8221;).<\/p>\n<p>So, you might ask &#8211; what&#8217;s the point?<\/p>\n<p>All I&#8217;ll say for now is that there are some times when &#8220;boring is good&#8221;. \u00a0Ethers, as we&#8217;ll learn later, can be useful as &#8220;protective groups&#8221; for masking (reactive) alcohols. But that&#8217;s a later discussion. [<em>See: <a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/06\/17\/protecting-groups-for-alcohols\/\">Protecting Groups For Alcohols<\/a><\/em>]<\/p>\n<p>Right now, let&#8217;s dig in to how this ether cleavage reaction works, because it actually does have its subtleties. This discussion should be pretty straightforward if you&#8217;ve been following along, however, because it&#8217;s just going to involve the familiar mechanisms of protonation, S<sub>N<\/sub>1 and S<sub>N<\/sub>2.<\/p>\n<h2><b><a id=\"two\"><\/a>2. The First Step In Acidic Cleavage Of\u00a0 Ethers Is Protonation Of Oxygen<\/b><\/h2>\n<p>Neutral ethers are generally resistant to nucleophiles in substitution reactions &#8211; that&#8217;s because the leaving group would have to be RO- , which is a very strong base.<\/p>\n<p>For that reason, the first step in any ether cleavage is protonation by a strong acid. Why does protonation help us? Remember that the &#8220;conjugate acid is always a better leaving group&#8221; . \u00a0Protonation of the ether allows for loss of ROH as a leaving group, which is a vastly weaker base than RO- .\u00a0\u00a0This is going to set up our next step &#8211; cleavage of one of the C\u2013O bonds.<\/p>\n<p>The usual strong acid of choice is usually hydroiodic acid (HI). Not only is it powerful (pK<sub>a<\/sub> of \u201310), as we&#8217;ll see the iodide counter-ion plays a role as well.<\/p>\n<h2><a id=\"three\"><\/a>3. For Methyl And Primary Ethers, The Second Step Of Ether Cleavage Is S<sub>N<\/sub>2<\/h2>\n<p>After protonation, what happens next? If we start with\u00a0a primary ether like diethyl ether, we will have a good leaving group (ROH) on a primary carbon in the presence of a decent nucleophile (iodide ion). \u00a0Sound familiar? It should &#8211;<strong> these are ideal conditions for an S<sub>N<\/sub>2 reaction. \u00a0<\/strong>And that&#8217;s what happens.<\/p>\n<p>The product will be ROH and R-I .<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15154\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-ether-cleavage-with-hi-diethyl-ether-gives-ethanol-and-ethyl-iodide-ethanol-forms-ethyl-iodide-with-excess-hi.gif\" alt=\"ether cleavage with hi diethyl ether gives ethanol and ethyl iodide ethanol forms ethyl iodide with excess hi\" width=\"640\" height=\"292\" \/><\/p>\n<p>If an excess (2 equiv or more) of HI is present, that alcohol can be converted into an alkyl iodide through two subsequent steps (protonation \/ S<sub>N<\/sub>2).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15155\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-mechanism-for-ether-cleavage-of-diethyl-ether-uses-hi-protonate-ether-oxygen-sn2-by-iodide-then-second-iteration-with-hi.gif\" alt=\"mechanism for ether cleavage of diethyl ether uses hi protonate ether oxygen sn2 by iodide then second iteration with hi\" width=\"640\" height=\"426\" \/><\/p>\n<p>This &#8220;S<sub>N<\/sub>2&#8243; pathway will be dominant for primary and methyl ethers.<\/p>\n<h2><strong><a id=\"four\"><\/a>4. For Tertiary Ethers, The Second Step of Ether Cleavage Is S<sub>N<\/sub>1<\/strong><\/h2>\n<p>What about a symmetrical tertiary ether like di-<em>t<\/em>-butyl ether?<\/p>\n<p>Clearly the S<sub>N<\/sub>2 is not in play here, as the tertiary carbons are much too hindered for a backside attack. However, tertiary carbocations are relatively stable &#8211; and &#8220;ionization&#8221; (i.e. loss of a leaving group) leaves us with an alcohol (R-OH) and a tertiary carbocation, which can then be attacked by iodide ion to give R-I<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-36070\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2014\/11\/4-cleavage-of-tertiary-ethers-occurs-through-sn1-pathway-protonation-curved-arrow-mechanism-formation-of-carbocation-giving-alkyl-iodide.gif\" alt=\"cleavage of tertiary ethers occurs through sn1 pathway protonation curved arrow mechanism formation of carbocation giving alkyl iodide\" width=\"640\" height=\"436\" \/><\/a><\/p>\n<p>Again, if excess HI is present then that alcohol will be converted into an alkyl halide. We&#8217;ll have more about that to say in a few posts actually.<\/p>\n<h2><strong><a id=\"five\"><\/a>5. For Secondary Ethers, The Second Step Could Proceed Through A Mixture Of Either Pathway<\/strong><\/h2>\n<p>What about secondary ethers? I don&#8217;t have a good answer. S<sub>N<\/sub>1 and S<sub>N<\/sub>2 is a continuum. You&#8217;ll likely have a mixture of S<sub>N<\/sub>2 and S<sub>N<\/sub>1 pathways operating. If someone tells you they can look at an\u00a0ether like di-isopropyl ether and the S<sub>N<\/sub>2\u00a0or S<sub>N<\/sub>1 pathway will be 100% dominant, that&#8217;s just not true.<\/p>\n<h2><strong><a id=\"six\"><\/a>6. The Mechanism For The Cleavage Of Unsymmetrical Ethers Is Hard\u00a0 To Generalize (With One Exception!)<\/strong><\/h2>\n<p>Just as tricky as the case of secondary ethers is the case of &#8220;mixed&#8221; ethers. What if you have two different groups attached to the oxygen (&#8220;unsymmetrical ethers&#8221;). Which way is it going to break?<\/p>\n<p>For example, what about t-butyl methyl ether? When you treat it with acid, what happens first? Do you do an S<sub>N<\/sub>2 on the methyl group with iodide, or does it ionize to give a tertiary carbocation?<\/p>\n<p><strong>This is the type of question that<\/strong>\u00a0<strong>is NOT\u00a0easy to answer without\u00a0knowing the results of experiments.\u00a0<\/strong><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15157\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-question-is-what-happens-with-tert-butyl-methyl-ether-with-one-equivalent-of-hi-is-it-sn2-or-sn1-hard-to-say.gif\" alt=\"question is what happens with tert butyl methyl ether with one equivalent of hi is it sn2 or sn1 hard to say\" width=\"640\" height=\"325\" \/><\/p>\n<p>There are, however, a few cases of mixed ethers where there IS a straightforward answer.<\/p>\n<p>Take this question for example. What happens? The answer is very clear and it goes 100% one way. See if you can do it.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"41460\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"41460\"] {\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=\"41460\"] {\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=\"41460\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-41460\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-41460 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"41460\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-4zooe\" data-id=\"4zooe\">\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\/2291-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\/2291-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<h2><a id=\"seven\"><\/a>7. Intramolecular Cleavage of Ethers<\/h2>\n<p>All right. We&#8217;ve seen a few examples of ether cleavage with acid.<\/p>\n<p>Now let\u2019s take tetrahydrofuran (THF), a <strong>cyclic<\/strong> ether. And now let\u2019s add strong acid to it. What happens?<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15250\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-what-is-product-when-tetrahydrofuran-is-broken-up-using-h-i-to-give-new-product-intramolecular-cleavage-of-ether.gif\" alt=\"what is product when tetrahydrofuran is broken up using h i to give new product intramolecular cleavage of ether\" width=\"640\" height=\"155\" \/><\/p>\n<p>Don&#8217;t panic! It&#8217;s the same sequence of bonds that form and break as before.<\/p>\n<p>First, we protonate the oxygen to give the conjugate acid, which is now a better leaving group. Second, iodide ion then attacks the carbon, forming C\u2013I and breaking O\u2013C \u00a0[S<sub>N<\/sub>2 in this case].<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15251\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-mechanism-for-cleavage-of-tetrahydrofuran-thf-with-strong-acid-hi-to-give-alcohol-iodide-further-reaction-with-hi-will-give-diiodide.gif\" alt=\"mechanism for cleavage of tetrahydrofuran thf with strong acid hi to give alcohol iodide further reaction with hi will give diiodide\" width=\"640\" height=\"300\" \/><\/p>\n<p>It&#8217;s important to note that the bonds that form and break in <strong>intramolecular<\/strong> processes (rings forming or breaking) are fundamentally no different than those that form and break in intermolecular processes.<\/p>\n<h2><strong><a id=\"eight\"><\/a>8. Summary: Acidic Cleavage of Ethers<\/strong><\/h2>\n<p>OK. So ethers, as we&#8217;ve talked about them so far, ARE pretty boring. But (and there&#8217;s always a but) &#8211; there IS a special class of ethers which is, in fact, very interesting and very reactive. If you&#8217;ve covered alkenes, you&#8217;ve seen them before &#8211; but under a different name. Can you guess what functional group I&#8217;m talking about ? Next post!<\/p>\n<p><strong>Next Post &#8211; <a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/\">Epoxides, The Outlier Of The Ether Family<\/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\/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\/wp_quiz\/williamson-ether-synthesis\/\" class=\"\"><span>Williamson Ether Synthesis<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/02\/02\/opening-of-epoxides-with-acid\/\" class=\"\"><span>Opening of Epoxides With Acid<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/02\/10\/opening-of-epoxide-with-base\/\" class=\"\"><span>Epoxide Ring Opening With Base<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/06\/12\/intramolecular-reactions-of-alcohols-and-ethers\/\" class=\"\"><span>Intramolecular Reactions of Alcohols and Ethers<\/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<hr \/>\n<h2><a id=\"quizzes\"><\/a>Quiz Yourself!<\/h2>\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\/3313-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\/3314-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\/1571-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\/1685-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\/3407-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\/3408-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\/3409-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>Ethers are widely inert to a lot of conditions, and thus find common use as solvents (e.g. diethyl ether, THF (tetrahydrofuran), dioxane, glyme, and others). Ether cleavage generally requires strong acid and heat, which are forcing conditions. Alternatively, silane reagents can be used, which are reactive at room temperature.<\/p>\n<ol>\n<li><strong>A NEW METHOD FOR THE PREPARATION OF ORGANIC IODIDES<br \/>\n<\/strong>HERMAN STONE and HAROLD SHECHTER<br \/>\n<em>The Journal of Organic Chemistry<\/em><strong> 1950<\/strong>, <em>15<\/em> (3), 491-495<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo01149a008\">1021\/jo01149a008<\/a><br \/>\nInstead of using HI, which is expensive, one can use the combination of phosphoric acid + KI for ether cleavage, which generates HI <em>in situ.<\/em><\/li>\n<li><strong>1,4-DIIODOBUTANE<\/strong><br \/>\nHerman Stone and Harold Shechter<br \/>\n<em>Org. Synth<\/em>. <strong>1950<\/strong>, <em>30<\/em>, 33<br \/>\n<strong>DOI<\/strong>: <a href=\"http:\/\/www.orgsyn.org\/demo.aspx?prep=CV4P0321\">10.15227\/orgsyn.030.0033<\/a><br \/>\nThis procedure from <em>Organic Syntheses<\/em>, a reliable source of independently tested synthetic organic laboratory procedures, demonstrates the cleavage of THF with refluxing strong acid.<\/li>\n<li><strong>The Cleavage of Ethers by Hydrogen Bromide<\/strong><br \/>\nRobert L. Burwell and Milton E. Fuller<br \/>\n<em>Journal of the American Chemical Society<\/em> <strong>1957,<\/strong> <em>79<\/em> (9), 2332-2336<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01566a085\">10.1021\/ja01566a085<\/a><br \/>\nClassic paper on the cleavage of ethers with HBr.Below are a variety of papers using silane-based reagents for ether cleavage. The Nobel Laureate late Prof. George Olah did a lot of work in this area in the middle of his career.<\/li>\n<li><strong>Cleavage of Esters and Ethers with Iodotrimethylsilane<\/strong><br \/>\nTse\u2010Lok Ho Prof. Dr. George A. Olah<br \/>\n<em>Angew. Chem. Int. Ed.<\/em> <strong>1976<\/strong>, <em>15<\/em> (12), 774-775<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/onlinelibrary.wiley.com\/doi\/abs\/10.1002\/anie.197607741\">10.1002\/anie.197607741<\/a><\/li>\n<li><strong>Synthetic methods and reactions. 62. Transformations with chlorotrimethylsilane\/sodium iodide, a convenient in situ iodotrimethylsilane reagent<\/strong><br \/>\nGeorge A. Olah, Subhash C. Narang, B. G. Balaram Gupta, and Ripudaman Malhotra<br \/>\n<em>The Journal of Organic Chemistry<\/em> <strong>1979,<\/strong> <em>44<\/em> (8), 1247-1251<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo01322a012\">10.1021\/jo01322a012<\/a><\/li>\n<li><strong>Trichloro(methyl)silane\/Sodium Iodide, A New Regioselective Reagent for the Cleavage of Ethers<\/strong><br \/>\nGeorge A. Olah, Altaf Husain, B. G. Balaram Gupta, Subhash C. Narang<br \/>\n<em>Angew Chem. Int. Ed.<\/em> <strong>1981<\/strong>, <em>20<\/em> (8), 690-691<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/onlinelibrary.wiley.com\/doi\/abs\/10.1002\/anie.198106901\">10.1002\/anie.198106901<\/a><\/li>\n<li><strong>Silane\/iodine-based cleavage of esters and ethers under neutral conditions<\/strong><br \/>\nHo, T-L., Olah, G. A.<br \/>\n<em>Proc. Natl. Acad. Sci. USA<\/em>. <strong>1978<\/strong> Jan; <em>75 <\/em>(1):4-6.<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/www.pnas.org\/content\/75\/1\/4\">10.1073\/pnas.75.1.4<\/a><\/li>\n<li><strong>Synthetic Methods and Reactions; 32: Mild and Effective Cleavage of Esters and Ethers with Phenyltrimethylsilane\/Iodine Reagent<\/strong><br \/>\nG. A., Ho, T-L.<br \/>\n<em>Synthesis<\/em> <strong>1977,<\/strong> 417<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/www.thieme-connect.com\/products\/ejournals\/abstract\/10.1055\/s-1977-24423\">10.1055\/s-1977-24423<\/a><\/li>\n<li><strong>Mild cleavage of methoxymethyl (MOM) ethers with trimethylsilyl bromide<br \/>\n<\/strong>Stephen Hanessian, Daniel Delorme, Yves Dufresne<br \/>\n<em>Tetrahedron Lett.<\/em> <strong>1984<\/strong>, <em>25<\/em> (24), 2515-2518<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/www.sciencedirect.com\/science\/article\/pii\/S0040403901812193\">10.1016\/S0040-4039(01)81219-3<\/a><br \/>\nMOM ethers are commonly used as protecting groups for -OH in organic synthesis, and so strategies for selective deprotection of MOM ethers under mild cleavage are invaluable.<\/li>\n<li><strong>Synthetic Methods and Reactions; 951. Ceric Ammonium Nitrate-Catalyzed Oxidative Cleavage of Alkyl and Silyl Ethers with Sodium Bromate<\/strong><br \/>\nGeorge A. Olah, B. G. Balaram Gupta, Alexander P. Fung<br \/>\n<em>Synthesis<\/em> <strong>1980<\/strong>; <em>1980 <\/em>(11): 897-898<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/www.thieme-connect.com\/products\/ejournals\/abstract\/10.1055\/s-1980-29258\">10.1055\/s-1980-29258<\/a><br \/>\nThis does not use silane reagents, but is still an interesting reagent for ether cleavage.<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>Acidic Cleavage of Ethers Can Proceed Through an SN2 or SN1 Mechanism, Depending On The Structure Ethers do not undergo very many reactions. One key <\/p>\n","protected":false},"author":1,"featured_media":35239,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1420],"tags":[167,1036,444,1035,850,897],"post_folder":[],"class_list":["post-8631","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alcohols-epoxides-ethers","tag-alcohols","tag-alkyl-iodides","tag-cleavage","tag-ether-cleavage","tag-ethers","tag-hi"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Cleavage Of Ethers With Acid &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"Ether cleavage with acid always begins with protonation of the ether oxygen, followed by either SN1 or SN2 reaction depending on the structure of the ether.\" \/>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.masterorganicchemistry.com\/2014\/11\/19\/ether-cleavage\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Cleavage Of Ethers With Acid &#8211; 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