{"id":8703,"date":"2015-01-26T16:21:04","date_gmt":"2015-01-26T21:21:04","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=8703"},"modified":"2025-11-17T11:53:22","modified_gmt":"2025-11-17T17:53:22","slug":"epoxides-the-outlier-of-the-ether-family","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/","title":{"rendered":"Epoxides &#8211; The Outlier Of The Ether Family"},"content":{"rendered":"<p><strong>Properties and Synthesis of Epoxides<\/strong><em>\u00a0<\/em><\/p>\n<ul>\n<li>Epoxides (oxiranes) are cyclic ethers that have unusually high reactivity due to ring strain (about 25 kcal\/mol).<\/li>\n<li>The 3-membered ring of epoxides can be opened under both acidic and basic conditions.<\/li>\n<li>Epoxides can be synthesized from alkenes via epoxidation with a peroxyacid like <em>m<\/em>-CPBA, or from halohydrins via treatment with base.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-15159\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/0-summary-of-epoxides-much-more-reactive-than-normal-ethers-due-to-ring-strain-synthesis-through-halohydrin-formation.gif\" alt=\"summary of epoxides much more reactive than normal ethers due to ring strain synthesis through halohydrin formation\" width=\"630\" height=\"312\" \/><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Cleavage\u00a0 of Ethers Generally Requires Very\u00a0 Harsh Conditions<\/a><\/li>\n<li><a href=\"#two\">Epoxides (&#8220;Oxiranes&#8221;) Are An Unusually Reactive Type of Cyclic Ether<\/a><\/li>\n<li><a href=\"#three\">Epoxides React With Aqueous Acid Under Mild Conditions To Form Diols<\/a><\/li>\n<li><a href=\"#four\">Unlike Most Ethers, Epoxides Can Be Easily\u00a0 Cleaved With Aqueous Base<\/a><\/li>\n<li><a href=\"#five\">Synthesis of Epoxides (1): Reaction of Alkenes With A Peroxyacid<\/a><\/li>\n<li><a href=\"#six\">Synthesis of Epoxides (2): Treating Halohydrins With Base<\/a><\/li>\n<li><a href=\"#seven\">Opening Of Epoxides Gives Different Products\u00a0 Depending\u00a0 On Whether Acid Or Base Is Used<\/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><strong><a id=\"one\"><\/a>1. Cleavage of Ethers Generally Requires Very Harsh Conditions<\/strong><\/h2>\n<p>In the <a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/11\/19\/ether-cleavage\/\">last post<\/a>, I\u00a0wrote that ethers were quite possibly the most boring functional group of all, at least from the perspective of reactivity. This got some friendly <a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/11\/19\/ether-cleavage\/#comment-349795\">flak<\/a> from an inorganic chemist in the crowd, but for our purposes, it&#8217;s true. We only cover one reaction: how to cleave ethers with strong acid.<br \/>\nTo review, here&#8217;s what this reaction looks\u00a0like for several different ethers. Since an &#8220;ether&#8221; is a functional group with an oxygen connected to two carbons, this\u00a0also\u00a0includes cyclic cases such as the five membered and three membered cyclic ethers below.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15160\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-hi-strong-acid-cleaves-ethers-such-as-anisole-tetrahydrofurane-and-especially-ethylene-oxide-epoxide.gif\" alt=\"hi strong acid cleaves ethers such as anisole tetrahydrofurane and especially ethylene oxide epoxide\" width=\"600\" height=\"403\" \/><\/p>\n<p>In this reaction, we protonate the ether oxygen with strong acid [<span style=\"color: #993366;\"><em>making a good leaving group<\/em><\/span>] and one of the adjacent carbons is then attacked by a nucleophile [I- in this case] leading to the rupture of the C-O bond and formation of the alcohol and alkyl iodide shown above.<\/p>\n<p>Opening up a cyclic molecule is akin to taking off a belt: by opening up the &#8220;buckle&#8221; [i.e. breaking the C-O bond] we go from a &#8220;loop&#8221; back to a &#8220;strip&#8221;. It is the same with cyclic molecules &#8211; see how the second and third examples open to give linear products.<\/p>\n<p>By the way, that first example is the answer to the <a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/11\/19\/ether-cleavage\/#quiz\">quiz <\/a>at the bottom of the last post. The second example shows the cyclic ether tetrahydrofuran (THF), which you&#8217;ve probably seen in other contexts &#8211; as an organic solvent, for instance. The third example shows a class of molecules you&#8217;ve likely seen before but might not have thought of as an ether &#8211; the three-membered cyclic ethers we call &#8220;epoxides&#8221; [or sometimes, &#8220;<span style=\"color: #993366;\"><em>oxiranes<\/em><\/span>&#8220;].<\/p>\n<h2><strong><a id=\"two\"><\/a>2. Epoxides (&#8220;Oxiranes&#8221;) Are An Unusually Reactive Type of Cyclic Ether<\/strong><\/h2>\n<p>If you think of ethers as a generally staid,\u00a0stable, and\u00a0placid family of functional groups, epoxides are definitely the <strong>outlier<\/strong>.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15161 size-full\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-awkward-family-photos-outlier-of-the-family-epoxides.jpg\" alt=\"awkward family photos outlier of the family epoxides\" width=\"450\" height=\"629\" srcset=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-awkward-family-photos-outlier-of-the-family-epoxides.jpg 450w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-awkward-family-photos-outlier-of-the-family-epoxides-215x300.jpg 215w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-awkward-family-photos-outlier-of-the-family-epoxides-320x447.jpg 320w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-awkward-family-photos-outlier-of-the-family-epoxides-360x503.jpg 360w\" sizes=\"(max-width: 450px) 100vw, 450px\" \/><\/p>\n<p>What makes epoxides so unusual &#8211; and interesting?<\/p>\n<p>The interior bond angles of epoxides are about 60\u00b0. Contrast that with the &#8220;ideal&#8221; bond angle of 109.5\u00b0 for tetrahedral carbon, and you&#8217;ll appreciate that like cyclopropane discussed earlier, they possess considerable\u00a0<strong>ring strain.<\/strong><\/p>\n<p>This ring strain &#8211; about 25 kcal\/mol [<a href=\"#ref15\">Ref<\/a>]- has the effect of making them&#8221;spring-loaded&#8221; if you will, toward opening.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15162\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-epoxides-oxiranes-are-unusually-reactive-type-of-cyclic-ether-ring-strain-about-13-kcal-mol-only-have-cis-ring-junctions.gif\" alt=\"epoxides oxiranes are unusually reactive type of cyclic ether ring strain about 13 kcal mol only have cis ring junctions\" width=\"600\" height=\"307\" \/><\/p>\n<p>[<span style=\"color: #993366;\"><em>It&#8217;s important to keep one thing in mind when drawing epoxides, especially with respect to their position on rings. The two C-O bonds must always be on the same &#8220;face&#8221; of the\u00a0ring [i.e. making a\u00a0&#8220;cis&#8221; ring junction]. The &#8220;trans&#8221; ring junction version is too strained to exist<\/em><\/span>]<\/p>\n<p>Let&#8217;s look at some examples of how epoxides are more reactive than &#8220;regular&#8221; ethers.<\/p>\n<h2><strong><a id=\"three\"><\/a>3. Epoxides React With Aqueous Acid Under Mild Conditions To Form Diols<\/strong><\/h2>\n<p>First of all, <strong>they react with acid under much milder conditions<\/strong> than, say, diethyl ether. For example, treating an epoxide with aqueous acid [H<sub>3<\/sub>O+] will open an epoxide to provide a 1,2-diol [<span style=\"color: #993366;\"><em>often called a &#8220;vicinal diol&#8221; or a &#8220;glycol&#8221;<\/em><\/span>].<\/p>\n<p>Under the same conditions that open the epoxide, diethyl ether is inert [as are most ethers], although the ether can be converted to alcohols with high enough temperatures\u00a0 (&gt; 100\u00b0C) .<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15163\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-epoxides-cleaved-with-acid-under-much-milder-conditions-than-normal-ethers-like-aqueous-acid-h3o-gives-trans-diols.gif\" alt=\"epoxides cleaved with acid under much milder conditions than normal ethers like aqueous acid h3o gives trans diols\" width=\"600\" height=\"446\" \/><\/p>\n<p>[<span style=\"color: #993366;\"><em>We&#8217;ll explore this reaction of epoxides in more detail in subsequent posts<\/em><\/span>].<\/p>\n<h2><a id=\"four\"><\/a>4. Unlike Most Ethers, Epoxides Can Be Easily\u00a0 Cleaved With Aqueous Base<\/h2>\n<p>Secondly: unlike the vast majority of ethers, <strong>epoxides can also be cleaved with base<\/strong>. For example, treatment of an epoxide such as ethylene oxide\u00a0with sodium hydroxide in water similarly leads to formation of a vicinal diol [<span style=\"color: #993366;\"><em>this is &#8220;<a style=\"color: #993366;\" href=\"http:\/\/en.wikipedia.org\/wiki\/Ethylene_glycol\">ethylene glycol<\/a>&#8220;, by the way, a common component of antifreeze].<\/em><\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15164\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-unlike-most-ethers-epoxides-can-be-easily-cleaved-with-strong-base-like-naoh-or-naoet.gif\" alt=\"unlike most ethers epoxides can be easily cleaved with strong base like naoh or naoet\" width=\"600\" height=\"371\" \/><\/p>\n<p>Other nucleophiles besides hydroxide ion can be used to open ethers (<em>see post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/02\/10\/opening-of-epoxide-with-base\/\">Opening of Epoxides With Base<\/a><\/em>)<\/p>\n<p><strong>The key point to absorb here is that epoxides are not typical ethers, and thus deserve their own discussion.\u00a0<\/strong><\/p>\n<p>Let&#8217;s back up a bit.<\/p>\n<h2><strong><a id=\"five\"><\/a>5. Synthesis of Epoxides (1): Reaction of Alkenes With A Peroxyacid<\/strong><\/h2>\n<p>I mentioned that you&#8217;d likely seen epoxides before, likely when you covered the reaction of alkenes. There&#8217;s two important ways to make epoxides from alkenes, one &#8220;direct&#8221; and one &#8220;indirect&#8221;. Let&#8217;s review the first method.<\/p>\n<p>Treating an alkene\u00a0with a &#8220;peroxyacid&#8221; (that&#8217;s a carboxylic acid containing an extra oxygen) leads to direct formation of an epoxide. A popular peroxyacid for this purpose is<a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/06\/17\/reagent-friday-m-cpba-meta-chloroperoxybenzoic-acid\/\"><em> m<\/em>-CPBA<\/a> [m-chloroperoxybenzoic acid], although other peroxyacids of the general form RCO<sub>3<\/sub>H also find use. We talked about this reaction in more detail <strong>here.\u00a0\u00a0<\/strong>(<em>See post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/04\/02\/epoxidation-hydroxylation-cyclopropanation-alkene-mechanism\/\">Reactions of Alkenes &#8211; the Concerted Pathway<\/a><\/em>)<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15165\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-epoxides-can-be-synthesized-through-treatment-of-alkenes-with-peroxyacids-such-as-mcpba-gives-syn-product.gif\" alt=\"epoxides can be synthesized through treatment of alkenes with peroxyacids such as mcpba gives syn product\" width=\"600\" height=\"309\" \/><\/p>\n<h2><strong><a id=\"six\"><\/a>6. Synthesis of Epoxides (2): Treating Halohydrins With Base<\/strong><\/h2>\n<p>There&#8217;s a second way to make epoxides via a two-step process that I don&#8217;t believe we&#8217;ve covered here before.\u00a0\u00a0Starting with an alkene, if one adds a halogen (such as Br<sub>2 <\/sub>or Cl<sub>2<\/sub>) and water as solvent, we make a species known as a <strong>halohydrin<\/strong>. Treatment of a halohydrin with strong base (such as NaH or NaOH) leads to deprotonation of the OH to give O- , which then displaces the adjacent halide via S<sub>N<\/sub>2 reaction to provide the resulting epoxide. [<span style=\"color: #993366;\"><em>why deprotonation and not S<sub>N<\/sub>2? see <a style=\"color: #993366;\" href=\"#noteone\"><strong>Note 1<\/strong><\/a><\/em><\/span>]<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15166\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-second-way-to-synthesize-epoxides-is-through-formation-of-halohydrins-from-ethers-and-treat-with-base-giving-epoxides-has-to-be-trans.gif\" alt=\"second way to synthesize epoxides is through formation of halohydrins from ethers and treat with base giving epoxides has to be trans\" width=\"600\" height=\"423\" \/><\/p>\n<p>Note that stereochemistry is important here! S<sub>N<\/sub>2 reactions proceed via a backside attack, (<em>See post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/07\/04\/the-sn2-mechanism\/\">The SN2 Mechanism<\/a><\/em>) leading to inversion of configuration. If the halohydrin is &#8220;locked&#8221; in position (as part of a ring, for example) and the alkoxide [O- ] cannot approach the backside of the C-Br bond, then the S<sub>N<\/sub>2 cannot occur and therefore an epoxide will not be formed. Instructors love to ask questions like this, so be alert!<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15167\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/8-for-halohydrins-to-give-epoxides-oh-and-br-have-to-be-on-opposite-sides-of-the-ring-otherwise-backside-attack-not-possible.gif\" alt=\"for halohydrins to give epoxides oh and br have to be on opposite sides of the ring otherwise backside attack not possible\" width=\"600\" height=\"217\" \/><\/p>\n<h2><a id=\"seven\"><\/a>7. Opening Of Epoxides Gives Different Products\u00a0 Depending\u00a0 On Whether Acid Or Base Is Used<\/h2>\n<p>This post has given us a little taste of the properties, reactions, and synthesis of epoxides, but there are many more details to explore here. For example, if you are very observant, you might have noticed an odd thing about the reactions of that cyclohexane epoxide from the acid and base slides: it gives a different product depending on whether H<sub>3<\/sub>O+ or NaOH is added!<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15168\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/9-epoxide-opening-is-condition-dependent-if-you-use-basic-or-acidic-conditions-get-different-results-basic-is-sn2-like-acidic-is-sn1-like.gif\" alt=\"epoxide opening is condition dependent if you use basic or acidic conditions get different results basic is sn2 like acidic is sn1 like\" width=\"600\" height=\"292\" \/><\/p>\n<p>This isn&#8217;t a typo! This represents the actual pattern of reactivity of this epoxide. Isn&#8217;t it strange that NaOH and H<sub>3<\/sub>O+ should lead to different products. Why might that be?<\/p>\n<p>One hint: this is a consequence of\u00a0the fact that these reactions go through different mechanisms. Mechanisms that &#8211; believe it or not &#8211; we have seen before, in one form or another. However, this dichotomy of mechanism is a prime source of confusion for students on this topic, and again, one that tends to be heavily tested on exams.<\/p>\n<p>We&#8217;ll start to delve into this mystery in the next post &#8211; as well as explore the reactions of epoxides in greater detail.<\/p>\n<p><strong>Next Post &#8211; <a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/02\/02\/opening-of-epoxides-with-acid\/\">Opening Of Epoxides 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\/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\/2011\/06\/17\/reagent-friday-m-cpba-meta-chloroperoxybenzoic-acid\/\" class=\"\"><span>Epoxidation of alkenes with m-CPBA (meta-chloroperoxybenzoic acid)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/reaction-guide\/formation-of-epoxides-from-bromohydrins\/\" class=\"\"><span>Formation of epoxides from bromohydrins (MOC Reaction Guide)<\/span><\/a><\/li><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\/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\/reaction-guide\/reaction-of-epoxides-with-nucleophiles-under-basic-conditions\/\" class=\"\"><span>Reaction of epoxides with nucleophiles under basic conditions (MOC Membership)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/07\/04\/the-sn2-mechanism\/\" class=\"\"><span>The SN2 Mechanism<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/05\/21\/acid-base-reactions-are-fast\/\" class=\"\"><span>Acid Base Reactions Are Fast<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/reaction-guide\/corey-chaykovsky-epoxides-from-addition-of-sulfur-ylides-to-aldehydes-and-ketones\/\" class=\"\"><span>Epoxides From Addition of Sulfur Ylides To Aldehydes and Ketones (Corey-Chaykovsky)<\/span><\/a><\/li><\/ul><\/div>\n<p><strong><a id=\"noteone\"><\/a>Note 1. <\/strong>By the way: you might ask &#8211; why doesn&#8217;t NaOH just do a backside attack on the C-Br bond in the first example? The answer is that <a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/05\/21\/acid-base-reactions-are-fast\/\">acid-base reactions tend to be fast relative to substitution reactions<\/a>, because there is very little atomic reorganization required. Secondly, once the alcohol has been deprotonated, the <strong>intra<\/strong>molecular S<sub>N<\/sub>2 reaction [forming the epoxide] is faster\u00a0than the <strong>inter<\/strong>molecular S<sub>N<\/sub>2 forming a new alcohol, because the proximity of the O- to the C-Br gives it a higher &#8220;effective concentration&#8221;. ]<\/p>\n<p><strong>Note 2.\u00a0<\/strong>Some bond dissociation energies of C-O bonds in cyclic ethers<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-40759\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/06\/F1-table-of-bond-dissociation-energies-in-cyclic-ethers-based-on-studies-of-cox.gif\" alt=\"table of bond dissociation energies in cyclic ethers based on studies of cox\" width=\"640\" height=\"470\" \/><\/a><\/p>\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\/3259-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\/3260-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\/3261-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\/3262-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\/3263-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\/3264-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\/3265-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\/3266-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><strong>Epoxide formation from halohydrins:<\/strong><\/p>\n<p>This reaction can be considered as an internal Williamson Ether Synthesis.<\/p>\n<ol>\n<li><strong>CYCLOHEXENE OXIDE<br \/>\n<\/strong>A. E. Osterberg<br \/>\n<em>Org. Synth.<\/em> <strong>1925<\/strong>, <em>5,<\/em> 35<br \/>\n<strong>DOI<\/strong>: <a href=\"http:\/\/orgsyn.org\/demo.aspx?prep=CV1P0185\">10.15227\/orgsyn.005.0035<\/a><br \/>\nSimple, straightforward <em>Organic Syntheses<\/em> prep of cyclohexene oxide from the chlorohydrin.<\/li>\n<li><strong>Kinetics of formation of substituted styrene oxides by reaction of 2-aryl- and 1-aryl-2-halogenoethanols with aqueous alkali<br \/>\n<\/strong>Anthony C. Knipe<br \/>\n<em>J. Chem. Soc. Perkin Trans. 2 <\/em><strong>1973, <\/strong>589-595<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.rsc.org\/en\/Content\/ArticleLanding\/P2\/1973\/P29730000589#!divAbstract\">10.1039\/P29730000589<\/a><br \/>\nThis paper studies the kinetics of styrene oxide formation using a Hammett plot, a classic tool of physical organic chemistry.<\/li>\n<li><strong>Stereochemical Aspects of the Synthesis of 1,2\u2010Epoxides<br \/>\n<\/strong>Giancarlo Berti<strong><br \/>\n<\/strong><em>Topics in Stereochemistry <\/em><strong>1973<\/strong>, 93<br \/>\n<strong>DOI:<\/strong><a href=\"https:\/\/onlinelibrary.wiley.com\/doi\/abs\/10.1002\/9780470147160.ch2\">1002\/9780470147160.ch2<\/a><br \/>\nSee page 187 in this review for a detailed discussion of the formation of epoxides from halohydrins.<\/li>\n<li><strong>Neighboring group effects in the regioselective cyclization of vicinal trans-1,2-bromohydrins to epoxides<\/strong><br \/>\nFengrui Lang, Darren J. Kassab, Bruce Ganem<br \/>\n<em>Tetrahedron Lett. <\/em><strong>1998<\/strong>, <em>39<\/em> (33), 5903-5906<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/www.sciencedirect.com\/science\/article\/abs\/pii\/S004040399801243X\">10.1016\/S0040-4039(98)01243-X<\/a><br \/>\nThe course of this intramolecular epoxide formation can also be influenced by neighboring group effects.<\/li>\n<li><strong>Diastereo- and enantioselective synthesis of \u03b1,\u03b2-epoxyketones using aqueous NaOCl in conjunction with dihydrocinchonidine derived phase-transfer catalysis at room temperature. Scope and limitations<br \/>\n<\/strong>Barry Lygo, Stuart D. Gardiner, Michael C. McLeod, and Daniel C. M. To<br \/>\n<em>Org.\u00a0 Biomol. Chem. <\/em><strong>2007,<\/strong> <em>5<\/em>, 2283-2290<br \/>\n<strong>DOI:<\/strong> <a href=\"https:\/\/pubs.rsc.org\/en\/content\/articlelanding\/2007\/ob\/b706546a#!divAbstract\">10.1039\/B706546A<\/a><br \/>\nEnantioselective epoxide-forming reactions are known, using chiral additives (e.g. dihydrocinchonidines).<strong>Epoxidation of alkenes with m-CPBA:<\/strong><\/li>\n<li><strong>Oxydation unges\u00e4ttigter Verbindungen mittels organischer Superoxyde<\/strong><br \/>\nNikolaus Prileschajew<br \/>\n<em>Chemische Berichte<\/em> <strong>1909<\/strong> <em>42<\/em>, 4811<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cber.190904204100\">10.1002\/cber.190904204100<\/a><br \/>\nThis reaction (epoxidations of alkenes with a peracid) is also known as the Prizelhaev reaction after the author.<\/li>\n<li><strong>The oxidation of olefins with perbenzoic acids. A kinetic study<br \/>\n<\/strong>B. M. Lynch and K. H. Pausacker<br \/>\n<em>J. Chem. Soc., <\/em><strong>1955<\/strong><em>, 1525-1531<\/em><br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.rsc.org\/en\/content\/articlelanding\/1955\/jr\/jr9550001525#!divAbstract\">10.1039\/JR9550001525<\/a><br \/>\nOne of the earliest papers on epoxidation with <em>m<\/em>-CPBA, comparing its reactivity with other substituted peracids. As expected, the reactivity of peroxyacids is increased by electron-withdrawing groups.<\/li>\n<li><strong>m-CHLOROPERBENZOIC ACID<br \/>\n<\/strong>Richard N. McDonald, Richard N. Steppel, and James E. Dorsey<br \/>\n<em>Org Synth.<\/em> Vol. 50, p.15 (1970)<br \/>\n<strong>DOI: <\/strong><a href=\"http:\/\/orgsyn.org\/demo.aspx?prep=CV6P0276\">10.15227\/orgsyn.050.0015<\/a><br \/>\nA reliable preparation for <em>m<\/em>-CPBA (which is commercially available) in <em>Organic Syntheses.<\/em> As this procedure shows, <em>m<\/em>-CPBA is not prepared as a pure compound (it is a mixture of the peracid and acid, and commercial samples may contain residual water for stability).<\/li>\n<li><strong>Epoxidations with m-Chloroperbenzoic Acid<br \/>\n<\/strong>Nelson N. Schwartz and John H. Blumbergs<br \/>\n<em>The Journal of Organic Chemistry<\/em> <strong>1964<\/strong> <em>29<\/em> (7), 1976-1979<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo01030a078\">1021\/jo01030a078<\/a><br \/>\nThis paper describes mechanistic studies of <em>m<\/em>-CPBA oxidation that demonstrate that ionic intermediates are not involved in the reaction, and that the rate is insensitive to solvent polarity.<\/li>\n<li>Bartlett, P. D.<br \/>\n<em>Rec. Chem. Prog<\/em>. <strong>1950<\/strong>, <em>11<\/em>, 47<br \/>\nThis is the publication in which Prof. P. D. Bartlett describes the \u2018butterfly mechanism\u2019 for <em>m-<\/em>CPBA epoxidation.<\/li>\n<li><strong>MCPBA Epoxidation of Alkenes:\u2009 Reinvestigation of Correlation between Rate and Ionization Potential<br \/>\n<\/strong>Cheal Kim, Teddy G. Traylor, and Charles L. Perrin<br \/>\n<em>Journal of the American Chemical Society<\/em> <strong>1998<\/strong> <em>120<\/em> (37), 9513-9516<br \/>\n<strong>DOI:<\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ja981531e\">1021\/ja981531e<\/a><br \/>\nAn interesting paper that describes the development of a kinetic method for measuring the rate of epoxidation of various alkenes with <em>m<\/em>-CPBA.<\/li>\n<li><strong>Experimental Geometry of the Epoxidation Transition State<\/strong><br \/>\nDaniel A. Singleton, Steven R. Merrigan, Jian Liu, and K. N. Houk<br \/>\n<em>Journal of the American Chemical Society<\/em> <strong>1997<\/strong> <em>119<\/em> (14), 3385-3386<br \/>\n<strong>DOI:<\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ja963656u\">1021\/ja963656u<\/a><br \/>\nCombined experimental and theoretical studies of the epoxidation transition state, showing that both C-O bond forming events are nearly synchronous.<\/li>\n<li><strong>The mechanism of epoxidation of olefins by peracids<\/strong><br \/>\nV. G. Dryuk<br \/>\n<em>Tetrahedron<\/em> Volume <em>32<\/em>, Issue 23, <strong>1976<\/strong>, Pages 2855-2866<br \/>\n<strong>DOI:<\/strong> <a href=\"https:\/\/www.sciencedirect.com\/science\/article\/abs\/pii\/0040402076801378\">10.1016\/0040-4020(76)80137-8<\/a><br \/>\nAn account of the author\u2019s work on kinetic studies of the epoxidation of olefins with peracids in order to determine the exact mechanism.<\/li>\n<li><strong><a id=\"ref15\"><\/a>Thermochemical Studies of Epoxides and Related Compounds<br \/>\n<\/strong>Kathleen M. Morgan, Jamie A. Ellis, Joseph Lee, Ashley Fulton, Shavonda L. Wilson, Patrick S. Dupart, and Rosanna Dastoori<strong><br \/>\n<\/strong><em>The Journal of Organic Chemistry<\/em><strong> 2013<\/strong>, <em>78<\/em> (9), 4303-4311<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo4002867\">1021\/jo4002867<\/a><br \/>\nTable 7 in this paper contains strain energies of cyclopropane, epoxides, aziridines, thiiranes, and the phosphorous analog (which is purely theoretical). Table 8 contains strain energies of epoxides. These values are obtained through computational methods, and are compared with experimentally derived values where possible. Oxirane has a strain energy of 27.3 kcal\/mol, which is reduced with alkyl substitution.<\/li>\n<\/ol>\n<p><strong>\u00a0<\/strong><em>Note &#8211; an earlier version of this article quoted a ring strain for epoxides of about 13 kcal\/mol. This is in error.\u00a0<\/em><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Properties and Synthesis of Epoxides\u00a0 Epoxides (oxiranes) are cyclic ethers that have unusually high reactivity due to ring strain (about 25 kcal\/mol). The 3-membered ring <\/p>\n","protected":false},"author":1,"featured_media":15159,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1420],"tags":[],"post_folder":[],"class_list":["post-8703","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alcohols-epoxides-ethers"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Epoxides - The Outlier Of The Ether Family &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"Epoxides are 3-membered cyclic ethers which are unusually reactive due to ring strain. Here we show how they are made (2 methods) and their reactions.\" \/>\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\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Epoxides - The Outlier Of The Ether Family &#8211; Master Organic Chemistry\" \/>\n<meta property=\"og:description\" content=\"Epoxides are 3-membered cyclic ethers which are unusually reactive due to ring strain. Here we show how they are made (2 methods) and their reactions.\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/\" \/>\n<meta property=\"og:site_name\" content=\"Master Organic Chemistry\" \/>\n<meta property=\"article:publisher\" content=\"https:\/\/www.facebook.com\/Master-Organic-Chemistry-242610599108055\/\" \/>\n<meta property=\"article:published_time\" content=\"2015-01-26T21:21:04+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2025-11-17T17:53:22+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/0-summary-of-epoxides-much-more-reactive-than-normal-ethers-due-to-ring-strain-synthesis-through-halohydrin-formation.gif\" \/>\n\t<meta property=\"og:image:width\" content=\"900\" \/>\n\t<meta property=\"og:image:height\" content=\"446\" \/>\n\t<meta property=\"og:image:type\" content=\"image\/gif\" \/>\n<meta name=\"author\" content=\"James Ashenhurst\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"James Ashenhurst\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"14 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\\\/\\\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/01\\\/26\\\/epoxides-the-outlier-of-the-ether-family\\\/#article\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/01\\\/26\\\/epoxides-the-outlier-of-the-ether-family\\\/\"},\"author\":{\"name\":\"James Ashenhurst\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/person\\\/78d83ec7d02b4b7365bade2cedaef80c\"},\"headline\":\"Epoxides &#8211; The Outlier Of The Ether Family\",\"datePublished\":\"2015-01-26T21:21:04+00:00\",\"dateModified\":\"2025-11-17T17:53:22+00:00\",\"mainEntityOfPage\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/01\\\/26\\\/epoxides-the-outlier-of-the-ether-family\\\/\"},\"wordCount\":2266,\"commentCount\":19,\"publisher\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#organization\"},\"image\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/01\\\/26\\\/epoxides-the-outlier-of-the-ether-family\\\/#primaryimage\"},\"thumbnailUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2019\\\/12\\\/0-summary-of-epoxides-much-more-reactive-than-normal-ethers-due-to-ring-strain-synthesis-through-halohydrin-formation.gif\",\"articleSection\":[\"Alcohols, Epoxides and Ethers\"],\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"CommentAction\",\"name\":\"Comment\",\"target\":[\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/01\\\/26\\\/epoxides-the-outlier-of-the-ether-family\\\/#respond\"]}]},{\"@type\":\"WebPage\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/01\\\/26\\\/epoxides-the-outlier-of-the-ether-family\\\/\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/01\\\/26\\\/epoxides-the-outlier-of-the-ether-family\\\/\",\"name\":\"Epoxides - The Outlier Of The Ether Family &#8211; Master Organic Chemistry\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#website\"},\"primaryImageOfPage\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/01\\\/26\\\/epoxides-the-outlier-of-the-ether-family\\\/#primaryimage\"},\"image\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/01\\\/26\\\/epoxides-the-outlier-of-the-ether-family\\\/#primaryimage\"},\"thumbnailUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2019\\\/12\\\/0-summary-of-epoxides-much-more-reactive-than-normal-ethers-due-to-ring-strain-synthesis-through-halohydrin-formation.gif\",\"datePublished\":\"2015-01-26T21:21:04+00:00\",\"dateModified\":\"2025-11-17T17:53:22+00:00\",\"description\":\"Epoxides are 3-membered cyclic ethers which are unusually reactive due to ring strain. Here we show how they are made (2 methods) and their reactions.\",\"breadcrumb\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/01\\\/26\\\/epoxides-the-outlier-of-the-ether-family\\\/#breadcrumb\"},\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"ReadAction\",\"target\":[\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/01\\\/26\\\/epoxides-the-outlier-of-the-ether-family\\\/\"]}]},{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/01\\\/26\\\/epoxides-the-outlier-of-the-ether-family\\\/#primaryimage\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2019\\\/12\\\/0-summary-of-epoxides-much-more-reactive-than-normal-ethers-due-to-ring-strain-synthesis-through-halohydrin-formation.gif\",\"contentUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2019\\\/12\\\/0-summary-of-epoxides-much-more-reactive-than-normal-ethers-due-to-ring-strain-synthesis-through-halohydrin-formation.gif\",\"width\":900,\"height\":446,\"caption\":\"summary of epoxides much more reactive than normal ethers due to ring strain synthesis through halohydrin formation\"},{\"@type\":\"BreadcrumbList\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2015\\\/01\\\/26\\\/epoxides-the-outlier-of-the-ether-family\\\/#breadcrumb\",\"itemListElement\":[{\"@type\":\"ListItem\",\"position\":1,\"name\":\"Home\",\"item\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/\"},{\"@type\":\"ListItem\",\"position\":2,\"name\":\"Epoxides &#8211; The Outlier Of The Ether Family\"}]},{\"@type\":\"WebSite\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#website\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/\",\"name\":\"Master Organic Chemistry\",\"description\":\"\",\"publisher\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#organization\"},\"potentialAction\":[{\"@type\":\"SearchAction\",\"target\":{\"@type\":\"EntryPoint\",\"urlTemplate\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/?s={search_term_string}\"},\"query-input\":{\"@type\":\"PropertyValueSpecification\",\"valueRequired\":true,\"valueName\":\"search_term_string\"}}],\"inLanguage\":\"en-US\"},{\"@type\":\"Organization\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#organization\",\"name\":\"Master Organic Chemistry\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/\",\"logo\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/logo\\\/image\\\/\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2019\\\/04\\\/cutmypic.png\",\"contentUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2019\\\/04\\\/cutmypic.png\",\"width\":225,\"height\":225,\"caption\":\"Master Organic Chemistry\"},\"image\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/logo\\\/image\\\/\"},\"sameAs\":[\"https:\\\/\\\/www.facebook.com\\\/Master-Organic-Chemistry-242610599108055\\\/\"]},{\"@type\":\"Person\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/person\\\/78d83ec7d02b4b7365bade2cedaef80c\",\"name\":\"James Ashenhurst\",\"image\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/secure.gravatar.com\\\/avatar\\\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g\",\"url\":\"https:\\\/\\\/secure.gravatar.com\\\/avatar\\\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g\",\"contentUrl\":\"https:\\\/\\\/secure.gravatar.com\\\/avatar\\\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g\",\"caption\":\"James Ashenhurst\"},\"description\":\"Ph.D. 2006, McGill University (James L. Gleason). Postdoctoral Associate, 2008-2010, Massachusetts Institute of Technology (M. Movassaghi). Founder, Master Organic Chemistry, 2010-present.\",\"sameAs\":[\"https:\\\/\\\/www.masterorganicchemistry.com\\\/about\\\/\"],\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/author\\\/james\\\/\"}]}<\/script>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Epoxides - The Outlier Of The Ether Family &#8211; Master Organic Chemistry","description":"Epoxides are 3-membered cyclic ethers which are unusually reactive due to ring strain. Here we show how they are made (2 methods) and their reactions.","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/","og_locale":"en_US","og_type":"article","og_title":"Epoxides - The Outlier Of The Ether Family &#8211; Master Organic Chemistry","og_description":"Epoxides are 3-membered cyclic ethers which are unusually reactive due to ring strain. Here we show how they are made (2 methods) and their reactions.","og_url":"https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/","og_site_name":"Master Organic Chemistry","article_publisher":"https:\/\/www.facebook.com\/Master-Organic-Chemistry-242610599108055\/","article_published_time":"2015-01-26T21:21:04+00:00","article_modified_time":"2025-11-17T17:53:22+00:00","og_image":[{"width":900,"height":446,"url":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/0-summary-of-epoxides-much-more-reactive-than-normal-ethers-due-to-ring-strain-synthesis-through-halohydrin-formation.gif","type":"image\/gif"}],"author":"James Ashenhurst","twitter_card":"summary_large_image","twitter_misc":{"Written by":"James Ashenhurst","Est. reading time":"14 minutes"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"Article","@id":"https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/#article","isPartOf":{"@id":"https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/"},"author":{"name":"James Ashenhurst","@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/person\/78d83ec7d02b4b7365bade2cedaef80c"},"headline":"Epoxides &#8211; The Outlier Of The Ether Family","datePublished":"2015-01-26T21:21:04+00:00","dateModified":"2025-11-17T17:53:22+00:00","mainEntityOfPage":{"@id":"https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/"},"wordCount":2266,"commentCount":19,"publisher":{"@id":"https:\/\/www.masterorganicchemistry.com\/#organization"},"image":{"@id":"https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/#primaryimage"},"thumbnailUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/0-summary-of-epoxides-much-more-reactive-than-normal-ethers-due-to-ring-strain-synthesis-through-halohydrin-formation.gif","articleSection":["Alcohols, Epoxides and Ethers"],"inLanguage":"en-US","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/","url":"https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/","name":"Epoxides - The Outlier Of The Ether Family &#8211; Master Organic Chemistry","isPartOf":{"@id":"https:\/\/www.masterorganicchemistry.com\/#website"},"primaryImageOfPage":{"@id":"https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/#primaryimage"},"image":{"@id":"https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/#primaryimage"},"thumbnailUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/0-summary-of-epoxides-much-more-reactive-than-normal-ethers-due-to-ring-strain-synthesis-through-halohydrin-formation.gif","datePublished":"2015-01-26T21:21:04+00:00","dateModified":"2025-11-17T17:53:22+00:00","description":"Epoxides are 3-membered cyclic ethers which are unusually reactive due to ring strain. Here we show how they are made (2 methods) and their reactions.","breadcrumb":{"@id":"https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/#breadcrumb"},"inLanguage":"en-US","potentialAction":[{"@type":"ReadAction","target":["https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/"]}]},{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/#primaryimage","url":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/0-summary-of-epoxides-much-more-reactive-than-normal-ethers-due-to-ring-strain-synthesis-through-halohydrin-formation.gif","contentUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/0-summary-of-epoxides-much-more-reactive-than-normal-ethers-due-to-ring-strain-synthesis-through-halohydrin-formation.gif","width":900,"height":446,"caption":"summary of epoxides much more reactive than normal ethers due to ring strain synthesis through halohydrin formation"},{"@type":"BreadcrumbList","@id":"https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/#breadcrumb","itemListElement":[{"@type":"ListItem","position":1,"name":"Home","item":"https:\/\/www.masterorganicchemistry.com\/"},{"@type":"ListItem","position":2,"name":"Epoxides &#8211; The Outlier Of The Ether Family"}]},{"@type":"WebSite","@id":"https:\/\/www.masterorganicchemistry.com\/#website","url":"https:\/\/www.masterorganicchemistry.com\/","name":"Master Organic Chemistry","description":"","publisher":{"@id":"https:\/\/www.masterorganicchemistry.com\/#organization"},"potentialAction":[{"@type":"SearchAction","target":{"@type":"EntryPoint","urlTemplate":"https:\/\/www.masterorganicchemistry.com\/?s={search_term_string}"},"query-input":{"@type":"PropertyValueSpecification","valueRequired":true,"valueName":"search_term_string"}}],"inLanguage":"en-US"},{"@type":"Organization","@id":"https:\/\/www.masterorganicchemistry.com\/#organization","name":"Master Organic Chemistry","url":"https:\/\/www.masterorganicchemistry.com\/","logo":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/logo\/image\/","url":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/04\/cutmypic.png","contentUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/04\/cutmypic.png","width":225,"height":225,"caption":"Master Organic Chemistry"},"image":{"@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/logo\/image\/"},"sameAs":["https:\/\/www.facebook.com\/Master-Organic-Chemistry-242610599108055\/"]},{"@type":"Person","@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/person\/78d83ec7d02b4b7365bade2cedaef80c","name":"James Ashenhurst","image":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/secure.gravatar.com\/avatar\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g","contentUrl":"https:\/\/secure.gravatar.com\/avatar\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g","caption":"James Ashenhurst"},"description":"Ph.D. 2006, McGill University (James L. Gleason). Postdoctoral Associate, 2008-2010, Massachusetts Institute of Technology (M. Movassaghi). Founder, Master Organic Chemistry, 2010-present.","sameAs":["https:\/\/www.masterorganicchemistry.com\/about\/"],"url":"https:\/\/www.masterorganicchemistry.com\/author\/james\/"}]}},"_links":{"self":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/posts\/8703","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/comments?post=8703"}],"version-history":[{"count":0,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/posts\/8703\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/media\/15159"}],"wp:attachment":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/media?parent=8703"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/categories?post=8703"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/tags?post=8703"},{"taxonomy":"post_folder","embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/post_folder?post=8703"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}