{"id":8738,"date":"2015-02-10T13:08:02","date_gmt":"2015-02-10T18:08:02","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=8738"},"modified":"2026-04-18T09:46:12","modified_gmt":"2026-04-18T14:46:12","slug":"opening-of-epoxide-with-base","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2015\/02\/10\/opening-of-epoxide-with-base\/","title":{"rendered":"Epoxide Ring Opening With Base"},"content":{"rendered":"<p><strong>Ring-opening of epoxides with basic nucleophiles<\/strong><\/p>\n<ul>\n<li>Epoxides are cyclic ethers with considerable ring strain (about 13 kcal\/mol)<\/li>\n<li>Epoxides undergo reaction with nucleophiles under basic conditions at the\u00a0<strong>least substituted\u00a0<\/strong>end of the epoxide<\/li>\n<li>If a chiral center is at this carbon, its stereochemistry will be inverted.<\/li>\n<li>Nucleophiles that will add to epoxides include hydroxide ion (HO-) alkoxides, Grignard reagents, organolithium reagents, and LiAlH<sub>4<\/sub> (among others)<\/li>\n<li>A simple way to remember this is to think of epoxide opening under basic conditions as proceeding much like an S<sub>N<\/sub>2 reaction.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-33286\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2015\/02\/0-reaction-of-epoxides-under-basic-conditions-via-sn2-reaction-with-naoh-and-h2o-attack-at-least-substituted-position-occurs-with-inversion-other-nucleophiles-possible.gif\" alt=\"reaction of epoxides under basic conditions via sn2 reaction with naoh and h2o attack at least substituted position occurs with inversion other nucleophiles possible\" width=\"641\" height=\"244\" \/><\/a><\/p>\n<p><strong>Table of Contents:\u00a0<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Opening Epoxides With Base: How it Works<\/a><\/li>\n<li><a href=\"#two\">The Role of Solvent<\/a><\/li>\n<li><a href=\"#three\">Understanding Separate Quench Steps: 1) Add this 2) THEN add this!<\/a><\/li>\n<li><a href=\"#four\">What Doesn&#8217;t Work: Poor Nucleophiles<\/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. Opening Epoxides With Base: How It Works<\/strong><\/h2>\n<p>In the <a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/02\/02\/opening-of-epoxides-with-acid\/\"><strong>last post<\/strong><\/a> we discussed the reactions of epoxides under acidic conditions and saw how they resembled the \u201c3-membered ring\u201d family of alkene mechanisms. We left off by noting that the reaction of the epoxide (shown above) \u00a0with NaOH in H<sub>2<\/sub>O gave a different product than that obtained through H<sub>3<\/sub>O+. \u00a0<strong>Therefore it must go through a different mechanism.\u00a0<\/strong><\/p>\n<p>Our question is, how does this reaction work?<\/p>\n<p>Noting the fact that the nucleophile (HO- \u00a0) attacks the epoxide at the least substituted position (C2) and results in inversion of stereochemistry at this position, <strong>our best evidence is consistent with this reaction proceeding through the familiar <a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/07\/04\/the-sn2-mechanism\/?_ga=1.173665187.1023948618.1419307631\">S<sub>N<\/sub>2 mechanism<\/a><\/strong> followed by a transfer of proton from the weakly acidic solvent (H<sub>2<\/sub>O) to the alkoxide (RO &#8211; ) providing a neutral alcohol.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-33287\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2015\/02\/1-opening-of-epoxide-under-basic-conditions-follows-sn2-mechanism-followed-by-protonation-giving-neutral-alcohol.gif\" alt=\"-opening of epoxide under basic conditions follows sn2 mechanism followed by protonation giving neutral alcohol\" width=\"640\" height=\"310\" \/><\/a><\/p>\n<p>Along the same lines,\u00a0 if epoxides are treated with alkoxides (RO- ) in alcohol solvent, they lead to essentially the same reaction. Here&#8217;s an example with NaOCH<sub>3<\/sub>. Note that the proton must come from CH<sub>3<\/sub>OH here.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15180\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-opening-of-epoxides-with-alkoxides-ro-occurs-via-sn2-reaction-inversion-at-least-substituted-carbon.gif\" alt=\"opening of epoxides with alkoxides ro occurs via sn2 reaction inversion at least substituted carbon\" width=\"640\" height=\"236\" \/><\/p>\n<h2><strong><a id=\"two\"><\/a>2. The Role Of Solvent<\/strong><\/h2>\n<p>Now &#8211; at the end of the last post, we mentioned that acids are incompatible with some strong nucleophiles because they will be destroyed by irreversible protonation [<span style=\"color: #993366;\"><em>classic example: Grignard reagents and water<\/em><\/span>]. Should we be worried about NaOH in H<sub>2<\/sub>O or NaOCH<sub>3<\/sub> in CH<sub>3<\/sub>OH? \u00a0No!\u00a0\u00a0These are examples of bases <span style=\"text-decoration: underline;\">in equilibrium<\/span> with their conjugate acids.<\/p>\n<p>It&#8217;s fine to have NaOH in the same reaction vessel with H<sub>2<\/sub>O since the reaction is reversible.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15181\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-role-of-solvent-is-that-alkodie-and-hydroxide-are-in-equilibrium-with-neutral-species-so-basicity-is-preserved-nucleophilicity-not-diminished.gif\" alt=\"role of solvent is that alkodie and hydroxide are in equilibrium with neutral species so basicity is preserved nucleophilicity not diminished\" width=\"640\" height=\"194\" \/><\/p>\n<p>However, if we move to more strongly basic nucleophiles, such as Grignard reagents (RMgX), organolithium reagents (R-Li) or hydrides (H-) we <b>should<\/b> be concerned, because the conjugate acids of each of these species (pK<sub>a<\/sub> of about 50 for alkanes, and about 38 for H<sub>2<\/sub>) are much weaker acids than ROH (pK<sub>a<\/sub> 16-18).<\/p>\n<p>[<span style=\"color: #993366;\"><em>A good rule of thumb for \u201creversibility\u201d of an acid base reaction is a pK<sub>a<\/sub> difference of 8 or less &#8211; see <a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/05\/17\/a-handy-rule-of-thumb-for-acid-base-reactions\/\">A Handy Rule of Thumb for Acid-Base Reactions<\/a><\/em><\/span>].<\/p>\n<p>That means that if these strong bases come into contact with ROH, an <strong>irreversible<\/strong> acid-base reaction will occur. We thus obtain an alkoxide (RO-)\u00a0 which is insufficient in strength to deprotonate alkanes or H<sub>2<\/sub>.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-33288\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2015\/02\/4-strong-bases-such-as-grignrads-organolithiums-nanh2-h-not-compatible-with-water-as-solvent-so-must-involve-second-quench-step-which-protonates-resulting-alkoxide.gif\" alt=\"strong bases such as grignrads organolithiums nanh2 h- not compatible with water as solvent so must involve second quench step which protonates resulting alkoxide\" width=\"639\" height=\"196\" \/><\/a><\/p>\n<p>Bye-bye nucleophile!<\/p>\n<h2><strong><a id=\"three\"><\/a>3.\u00a0 Understanding Separate Quench Steps: 1) Add this \u00a02) THEN, add this! \u00a0<\/strong><\/h2>\n<p>What this means in practice is that we just move the protonation step to the end, in a process sometimes called a \u201cquench\u201d. Note how each of the following reactions has a Step 1) and a Step 2).<\/p>\n<p>Step 1 is addition of nucleophile. <em>After the reaction is done<\/em>, we add our source of proton (Step 2) to quench. Note that there are many reagents commonly written for this process &#8211; H<sub>2<\/sub>O, H<sub>3<\/sub>O+, H+, NH<sub>4<\/sub>Cl, \u201cacid workup\u201d just to name a few. <strong>They all mean the same thing!<\/strong><\/p>\n<p>Here are some examples of reactions of epoxides with strongly basic nucleophiles. Grignard reagents , organolithium reagents, and hydride (e.g. LiAlH<sub>4<\/sub> , a source of H- ).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-33289\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2015\/02\/5-with-more-basic-nucleophiles-opening-epoxides-quencgh-step-is-separate-happens-during-workup-such-as-h-or-nh4cl-etc.gif\" alt=\"with more basic nucleophiles opening epoxides quencgh step is separate happens during workup such as h+ or nh4cl etc\" width=\"640\" height=\"499\" \/><\/a><\/p>\n<p>Is there anything else? [<span style=\"color: #993366;\"><em>yes &#8211; there are other nucleophiles which will react with epoxides, but they are seldom seen at this level. However I have added them in <a href=\"#noteone\">Note 1<\/a> at the bottom<\/em><\/span>].<\/p>\n<h2><strong><a id=\"four\"><\/a>4. What Doesn&#8217;t Work: Poor Nucleophiles<\/strong><\/h2>\n<p>Just like any S<sub>N<\/sub>2 reaction, for this pathway to work, we really must be dealing with a decent nucleophile. Poor nucleophiles, especially neutral species like H<sub>2<\/sub>O, ROH, and RCOOH simply won\u2019t cut it.<\/p>\n<p>In order for epoxides to react we need either to use strongly acidic conditions (good for weak nucleophiles) or basic conditions (HO- , RO- , RMgBr, RLi, LiAlH<sub>4<\/sub>).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15184\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-by-themselves-poor-nucleophiles-like-roh-water-carboxylic-acids-do-not-open-epoxides-not-strong-enough.gif\" alt=\"by themselves poor nucleophiles like roh water carboxylic acids do not open epoxides not strong enough\" width=\"640\" height=\"172\" \/><\/p>\n<p><em>This concludes our exploration of epoxides and ethers<\/em>. However we still have a lot to talk about regarding alcohols &#8211; and certainly we aren\u2019t done with examples of S<sub>N<\/sub>1 and S<sub>N<\/sub>2 reactions. That\u2019s coming up next.<\/p>\n<p><strong>Next Post &#8211; <a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/02\/27\/making-alkyl-halides-from-alcohols\/\">Making Alkyl Halides From Alcohols<\/a><\/strong><\/p>\n<hr \/>\n<h2><b><a id=\"notes\"><\/a>Notes<\/b><\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/02\/27\/making-alkyl-halides-from-alcohols\/\" class=\"\"><span>Making Alkyl Halides From Alcohols<\/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\/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\/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\/2012\/07\/04\/the-sn2-mechanism\/\" class=\"\"><span>The SN2 Mechanism<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/12\/10\/reactions-of-grignard-reagents\/\" class=\"\"><span>Reactions of Grignard Reagents<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/05\/17\/a-handy-rule-of-thumb-for-acid-base-reactions\/\" class=\"\"><span>A Handy Rule of Thumb for Acid-Base Reactions<\/span><\/a><\/li><\/ul><\/div>\n<p><strong><a id=\"noteone\"><\/a>Note 1. <\/strong>Some other nucleophiles which react with epoxides but are rarely seen in introductory organic chemistry. Note that the second and third examples don&#8217;t show the source of proton (H+) that adds to the oxygen, but it can be added afterwards in a \u00a0&#8220;quench&#8221; step.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15185\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F1-other-nucleophiles-that-open-epoxides-include-cyanide-ion-thiolate-and-azide.gif\" alt=\"other nucleophiles that open epoxides include cyanide ion thiolate and azide\" width=\"640\" height=\"319\" \/><\/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\/0693-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\/1398-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. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1400-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. <br \/>\n <\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1411-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. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1396-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. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1414-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. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1455-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<ol>\n<li><strong>\u2014The velocities of combination of sodium derivatives of phenols with olefine oxides<br \/>\n<\/strong>David Runciman Boyd and Ernest Robert Marle<strong><br \/>\n<\/strong><em>J. Chem. Soc., Trans.,<\/em><strong> 1914, <\/strong><em>105<\/em>, 2117-2139<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.rsc.org\/en\/content\/articlelanding\/1914\/ct\/ct9140502117\/unauth#!divAbstract\">10.1039\/CT9140502117<\/a><br \/>\nThis and the accompanying paper are early examples of ring-opening of epoxides with alkoxides.<\/li>\n<li><strong>\u2014The velocities of combination of sodium derivatives of phenols with olefine oxides. Part II<br \/>\n<\/strong>David Runciman Boyd and Miss Doris Feltham Thomas<br \/>\n<em>J. Chem. Soc., Trans.,<\/em><strong> 1919<\/strong>, <em>115<\/em>, 1239-1243<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.rsc.org\/en\/content\/articlelanding\/1919\/ct\/ct9191501239\/unauth#!divAbstract\">10.1039\/CT9191501239<\/a><\/li>\n<li><strong>CYCLOHEXENE IMINE<br \/>\n<\/strong>Iain D. G. Watson, Nicholas Afagh, and Andrei K. Yudin<br \/>\n<em>Org. Synth.<\/em><strong> 2010, <\/strong><em>87<\/em>, 161<strong><br \/>\nDOI: <\/strong><a href=\"http:\/\/www.orgsyn.org\/demo.aspx?prep=v87p0161\">10.15227\/orgsyn.087.0161<\/a><br \/>\nThe first reaction in this procedure from <em>Organic Syntheses<\/em> is the ring-opening of cyclohexene oxide with sodium azide. As Prof. Yudin shows, this reaction is a useful precursor for the synthesis of N-H aziridines, the nitrogen analog of epoxides.<\/li>\n<li><strong>The Reaction of Dimethylmagnesium and of Diethylmagnesium with Cyclohexene Oxide<br \/>\n<\/strong>Paul D. Bartlett and C. Manly Berry<\/p>\n<div><cite>Journal of the American Chemical Society<\/cite>\u00a0<strong>1934<\/strong>\u00a0<em>56<\/em>\u00a0(12), 2683-2685<\/div>\n<p><strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ja01327a045\">10.1021\/ja01327a045<\/a>This is an early example of ring-opening of epoxides with Grignard reagents.<\/li>\n<li><strong>The stereochemical course of epoxide ring opening by allylic grignard reagents<br \/>\n<\/strong>Hugh Felkin, Georges Roussi<strong><br \/>\n<\/strong><em>Tetrahedron Lett.<\/em> <strong>1965<\/strong>, <em>6<\/em> (46), 4153-4159<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/www.sciencedirect.com\/science\/article\/pii\/S0040403901995814\">10.1016\/S0040-4039(01)99581-4<\/a><br \/>\nThis is a more advanced (and perhaps less relevant) paper, attempting to resolve whether allylic Gringard reagents go through an S<sub>N<\/sub>2\u2019 reaction. This could be resolved easily with isotopic labeling and <sup>13<\/sup>C NMR.<\/li>\n<li><strong>Acid- and base-catalyzed ring-opening reactions or a sterically hindered epoxide<br \/>\n<\/strong>Herbert Mayr, Rainer Koschinsky, Elfriede Will, and Englbert Bauml<strong><br \/>\n<\/strong><em>The Journal of Organic Chemistry<\/em><strong> 1987<\/strong>, <em>52<\/em> (7), 1342-1344<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo00383a033\">1021\/jo00383a033<\/a><strong><br \/>\n<\/strong>A nice paper describing the different products obtained when opening a hindered epoxide under acidic vs. basic conditions. Prof. Mayr (LMU, Germany) is well known for his extremely rigorous work in physical organic chemistry, where he has developed scales for quantifying electrophilicity and nucleophilicity.<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>Ring-opening of epoxides with basic nucleophiles Epoxides are cyclic ethers with considerable ring strain (about 13 kcal\/mol) Epoxides undergo reaction with nucleophiles under basic conditions <\/p>\n","protected":false},"author":1,"featured_media":15178,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1420],"tags":[1044,167,1029,1045,626,470,215,254,271],"post_folder":[],"class_list":["post-8738","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alcohols-epoxides-ethers","tag-acid-base","tag-alcohols","tag-alkoxide","tag-alkyllithiums","tag-epoxide-opening","tag-epoxides","tag-grignards","tag-pka","tag-sn2"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Epoxide Ring Opening With Base &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"Epoxide ring opening with base can be performed with hydroxide ion, alkoxides, Grignard reagents and several other nucleophiles. It proceeds through SN2.\" \/>\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\/02\/10\/opening-of-epoxide-with-base\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Epoxide Ring Opening With Base &#8211; Master Organic Chemistry\" \/>\n<meta property=\"og:description\" content=\"Epoxide ring opening with base can be performed with hydroxide ion, alkoxides, Grignard reagents and several other nucleophiles. 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