{"id":26157,"date":"2023-01-18T16:17:32","date_gmt":"2023-01-18T22:17:32","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=26157"},"modified":"2026-04-11T05:46:27","modified_gmt":"2026-04-11T10:46:27","slug":"where-will-substitution-elimination-reactions-occur","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2023\/01\/18\/where-will-substitution-elimination-reactions-occur\/","title":{"rendered":"Identifying Where Substitution and Elimination Reactions Happen"},"content":{"rendered":"<p><strong>Identifying Carbons Where Substitution and Elimination Reactions Can Take Place<\/strong><\/p>\n<ul>\n<li>Substitution and elimination reactions need a <strong>leaving group<\/strong> in order for them to occur.<\/li>\n<li>Look for a good\u00a0<strong>leaving group<\/strong> on the substrate undergoing the substitution or elimination reaction.<\/li>\n<li>If there is <strong>no<\/strong> good leaving group, then there <strong>won&#8217;t<\/strong> be a substitution or elimination reaction. It&#8217;s that simple.<\/li>\n<li>What makes a good leaving group? Review here (<span style=\"color: #993366;\"><em>See Article: <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/04\/12\/what-makes-a-good-leaving-group\/\">What Makes a Good Leaving Group<\/a><\/em><\/span>), but the bottom line is look for <strong>halogens<\/strong> and other species that are <strong>weak bases<\/strong>.<\/li>\n<li>Hydroxyl groups (HO-) are poor leaving groups unless acid is present.<\/li>\n<li>Furthermore, S<sub>N<\/sub>1\/S<sub>N<\/sub>2 and E1\/E2 generally only happen on <em>sp<sup>3<\/sup><\/em>-hybridized carbons.<\/li>\n<li><em>sp<\/em><sup>2<\/sup>-hybridized carbons such as alkenyl, aryl and alkynyl halides will <strong>not<\/strong> undergo S<sub>N<\/sub>1\/S<sub>N<\/sub>2\/E1\/E2<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-33956\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/0-summary-where-will-sn1-sn2-e1-e2-reactions-occur-sp3-hybridized-alkyl-halides-mostly.gif\" alt=\"summary-where will sn1 sn2 e1 e2 reactions occur - sp3 hybridized alkyl halides mostly\" width=\"640\" height=\"603\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Look For A Good Leaving Group On The Substrate<\/a><\/li>\n<li><a href=\"#two\">The Leaving Group Must Be On An sp<sup>3<\/sup> Hybridized Carbon<\/a><\/li>\n<li><a href=\"#three\">Identify The Type of Carbon As Primary, Secondary, or Tertiary<\/a><\/li>\n<li><a href=\"#four\">Acid Makes Alcohols (and Ethers) Into Better Leaving Groups<\/a><\/li>\n<li><a href=\"#five\">Multiple Functional Groups<\/a><\/li>\n<li><a href=\"#six\">Epoxides<\/a><\/li>\n<li><a href=\"#seven\">Summary<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quiz\">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. Look For A Good Leaving Group On The Substrate<\/h2>\n<p>This article presumes you are familiar with the S<sub>N<\/sub>1, S<sub>N<\/sub>2, E1, and E2 reactions. If you need a review on any of these reactions, please follow these links and then come back.<\/p>\n<ul>\n<li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/07\/13\/the-sn1-mechanism\/\">The SN1 Reaction<\/a><\/li>\n<li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/07\/04\/the-sn2-mechanism\/\">The SN2 Reaction<\/a><\/li>\n<li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/09\/19\/the-e1-reaction\/\">The E1 Reaction<\/a><\/li>\n<li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/09\/27\/the-e2-mechanism\/\">The E2 Reaction<\/a><\/li>\n<\/ul>\n<p>In nucleophilic <strong>substitution<\/strong> reactions, the <strong>substrate <\/strong>or <strong>electrophile <\/strong>(an electron-pair acceptor, e.g. an alkyl halide) undergoes attack by a <strong>nucleophile<\/strong> (the electron-pair donor).\u00a0 A\u00a0new carbon-nucleophile bond <strong>forms<\/strong>, and a carbon-leaving group bond <strong>breaks\u00a0<\/strong>off from the substrate.<\/p>\n<p>In <strong>elimination<\/strong> reactions, a\u00a0<strong>base<\/strong> breaks a C-H bond on the substrate, and a new C-C pi bond <strong>forms<\/strong>, with the <strong>breaking <\/strong>of a carbon-leaving group bond from the substrate.<\/p>\n<p>Both of these reactions require the\u00a0<strong>loss of a leaving group\u00a0<\/strong>from the substrate (i.e. the molecule which is accepting a lone pair from the nucleophile, or is being deprotonated by a base).<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-33888\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/1-how-leaving-groups-work-in-substitution-and-elimination-reactions.gif\" alt=\"how leaving groups work in substitution and elimination reactions\" width=\"640\" height=\"428\" \/><\/a><\/p>\n<p>If there&#8217;s no good leaving group on the substrate&#8230; then no substitution or elimination reaction can happen! It&#8217;s that simple.<\/p>\n<p>Common examples of\u00a0<strong>good\u00a0<\/strong>leaving groups are species that can be\u00a0<strong>weak bases<\/strong> once they accept a lone pair of electrons:<\/p>\n<ul>\n<li>Halogens (Cl, Br, I, but not F, as the C-F bond is very strong)<\/li>\n<li>Sulfonates [OTs or OMs]<\/li>\n<li>Acyloxy groups (O-C(O)R)<\/li>\n<li>Positively charged groups containing oxygen [OH<sub>2 <\/sub>(+),\u00a0 OH(R)(+)], nitrogen [NR<sub>3<\/sub>(+)], or even sulfur [SR<sub>2<\/sub>(+)]<\/li>\n<\/ul>\n<p><img decoding=\"async\" class=\"alignnone wp-image-33889\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/2-partial-list-of-good-groups-in-nucleophilic-substitution-reactions-and-elimination.gif\" alt=\"partial list of good groups in nucleophilic substitution reactions and elimination\" width=\"640\" height=\"343\" \/><\/a><\/p>\n<p>(<em><span style=\"color: #993366;\">There is an excellent correlation\u00a0 between low pK<sub>a<\/sub> and leaving group ability of the conjugate base. <\/span><\/em><span style=\"color: #993366;\"><em>For more on this, see article: <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/04\/12\/what-makes-a-good-leaving-group\/\">What Makes A Good Leaving Group?<\/a><\/em><\/span>)<\/p>\n<p>Examples of\u00a0<strong>poor\u00a0<\/strong>leaving groups include strong bases such as hydroxide (HO<sup>\u2013<\/sup>), alkoxides, amides (NH<sub>2<\/sub><sup>\u2013<\/sup>)hydride (H<sup>\u2013<\/sup>) and carbanions (R<sup>\u2013<\/sup>). The fluoride ion (F<sup>\u2013<\/sup>) also tends to be a poor leaving group in substitution and elimination reactions since it forms extremely <strong>strong<\/strong> bonds to carbon. [<a href=\"#noteone\"><span style=\"color: #ff0000;\">Note 1<\/span><\/a>] The cyano group (CN) is a weak base but does not tend to act as a leaving group in substitution or elimination reactions. [<a href=\"#notetwo\"><span style=\"color: #ff0000;\">Note 2<\/span><\/a>]<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-33890\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/3-a-partial-list-of-poor-leaving-groups-in-nucleophilic-substitution-and-elimination.gif\" alt=\"a partial list of poor leaving groups in nucleophilic substitution and elimination\" width=\"640\" height=\"270\" \/><\/a><\/p>\n<p>So the first order of business in determining the product of any of these reactions is to\u00a0<strong>identify the site(s) on the substrate where there is a good leaving group.\u00a0<\/strong><\/p>\n<p>In other words, look for groups that will be <strong>weak bases<\/strong> when they accept a lone pair of electrons.<\/p>\n<p>Not all molecules are capable of substitution or elimination!<\/p>\n<p>For example, hydrocarbons do not act as <strong>substrates<\/strong> in S<sub>N<\/sub>1\/S<sub>N<\/sub>2 or elimination reactions because the leaving groups would have to be the extremely strong bases H(-) or alkyl anions (e.g. CH<sub>3<\/sub>(-) ).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-33891\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/4-hydrocarbons-do-not-undergo-substitution-or-elimination.gif\" alt=\"hydrocarbons do not undergo substitution or elimination\" width=\"640\" height=\"303\" \/><\/a><\/p>\n<p><span style=\"color: #993366;\"><em>Some hydrocarbons can act as <strong>nucleophiles<\/strong> in substitution and elimination reactions, but that&#8217;s different than being the\u00a0<strong>substrate. (See post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/05\/01\/the-2-most-important-reactions-of-alkynes\/\">Acetylides from Alkynes And Their Use In Substitution Reactions<\/a>)<\/strong><\/em><\/span><\/p>\n<p>These exercises give you the challenge of identifying sites on a molecule where substitution or elimination can occur.<\/p>\n<p>If you identify the leaving group, then you are identifying at least one of the bonds that will break. You are halfway there!<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"34829\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"34829\"] {\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=\"34829\"] {\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=\"34829\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-34829\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-34829 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"34829\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-rpg1r\" data-id=\"rpg1r\">\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\/2419-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\/2419-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>Here&#8217;s another set of examples.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"34830\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"34830\"] {\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=\"34830\"] {\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=\"34830\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-34830\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-34830 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"34830\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-qb95l\" data-id=\"qb95l\">\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\/2420-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\/2420-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>As these quizzes should hopefully have driven home, you want to look for\u00a0<strong>halogens<\/strong>,\u00a0<strong>sulfonates<\/strong>, or other species that will be <strong>weak bases<\/strong> once they depart from the substrate.<\/p>\n<p>Some groups that are poor leaving groups can be made into better leaving groups through the addition of\u00a0<strong>acids.\u00a0<\/strong>More on that<strong>\u00a0<\/strong>below.<\/p>\n<h2><a id=\"two\"><\/a>2. The Good Leaving Group Should Be Attached To An <em>sp<\/em><sup>3<\/sup> Hybridized Carbon<\/h2>\n<p>In substitution and elimination reactions, the transition state generally involves the formation of <strong>partial positive<\/strong> charge at the carbon bearing the leaving group.<\/p>\n<p>Carbocations are most stable when they are formed through the loss of a leaving group on an <em>sp<\/em><sup>3<\/sup>-hybridized carbon. Removing a leaving group from an <em>sp<\/em><sup>2<\/sup> or <em>sp<\/em>-hybridized carbon is very difficult, since the greater s-character means the electrons are held closer to the nucleus. [<span style=\"color: #993366;\"><em>See article: <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/03\/11\/3-factors-that-stabilize-carbocations\/\">Carbocation Stability<\/a><\/em><\/span>] [<a href=\"#notethree\"><span style=\"color: #ff0000;\">Note 3<\/span><\/a>]<\/p>\n<p>So another key to identifying where a nucleophilic substitution or elimination reaction will occur is to\u00a0<strong>examine the carbon attached to the good leaving group.\u00a0<\/strong><\/p>\n<ul>\n<li>If the leaving group is attached to an <em>sp<\/em><sup>3<\/sup> hybridized carbon, then this is a <strong>good<\/strong> candidate for the site of the reaction.<\/li>\n<li>If it is attached to an <em>sp<\/em><sup>2<\/sup> or <em>sp<\/em>\u00a0hybridized carbon, then it is <strong>unlikely<\/strong> to undergo nucleophilic substitution or elimination.<\/li>\n<\/ul>\n<p>In this exercise, identify the carbon atoms which are capable of undergoing substitution or elimination.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"34831\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"34831\"] {\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=\"34831\"] {\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=\"34831\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-34831\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-34831 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"34831\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-gjfz8\" data-id=\"gjfz8\">\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\/2421-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\/2421-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>Here is another set of examples.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"34832\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"34832\"] {\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=\"34832\"] {\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=\"34832\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-34832\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-34832 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"34832\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-8muq8\" data-id=\"8muq8\">\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\/2422-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\/2422-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>It&#8217;s important to know the few exceptions. [<a href=\"#notefour\"><span style=\"color: #ff0000;\">Note 4<\/span><\/a>] Elimination to give alkynes occurs on <em>sp<\/em><sup>2<\/sup> hybridized carbon using the extremely strong base NaNH<sub>2<\/sub>. [<span style=\"color: #993366;\"><em>See article: <a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/06\/11\/alkynes-via-elimination-reactions\/\">Alkynes via Elimination Reactions<\/a><\/em><\/span>]. <span style=\"color: #993366;\"><em>Another exception, more common in advanced courses, is a reaction related to the S<sub>N<\/sub>2 called the S<sub>N<\/sub>2-prime (S<sub>N<\/sub>2&#8242;) where formation of C-Nu and breakage of C-LG is accompanied by the shifting over of a C-C pi bond. [<a href=\"#notefive\">Note 5<\/a>]<\/em><\/span><\/p>\n<h2><a id=\"three\"><\/a>3. Identify The Carbon Attached To The Leaving Group As Primary, Secondary or Tertiary<\/h2>\n<p>Once a plausible site for substitution or elimination has been found, the next step is to be able to classify that carbon as <strong>primary<\/strong>, <strong>secondary<\/strong> or <strong>tertiary<\/strong>.<\/p>\n<p>Why is this important?\u00a0 Because it will greatly help in determining whether a reaction proceeds via SN1, SN2, E1 or E2 pathway.<\/p>\n<p>I have more to say on this in the subsequent article (<span style=\"color: #800080;\"><em>See article: <a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/11\/21\/deciding-sn1sn2e1e2-1-the-substrate\/\">SN1\/SN2\/E1\/E2 &#8211; The Substrate<\/a><\/em><\/span>)<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"34808\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"34808\"] {\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=\"34808\"] {\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=\"34808\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-34808\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-34808 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"34808\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-ojb3y\" data-id=\"ojb3y\">\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\/2349-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\/2349-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>Here is another quiz:<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"34834\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"34834\"] {\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=\"34834\"] {\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=\"34834\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-34834\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-34834 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"34834\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-xlopt\" data-id=\"xlopt\">\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\/2423-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\/2423-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=\"four\"><\/a>4. Alcohols And Ethers Can Participate In Substitution and Elimination Reactions If Acid Is Present<\/h2>\n<p>If you have made it this far, and have not covered alcohols or epoxides, then you are probably ready to proceed to the next article.<\/p>\n<p>If you are covering the substitution and elimination reactions of alcohols and ethers, however, you&#8217;ll need to know another important twist.<\/p>\n<p>Hydroxyl groups (OH) are poor leaving groups in substitution and elimination reactions.\u00a0<strong>Unless\u00a0<\/strong>strong acid is present, in which case they can be protonated to give their conjugate acids. (<span style=\"color: #993366;\"><em>See article: <a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/08\/07\/the-conjugate-acid-is-a-better-leaving-group\/\">The Conjugate Acid Is A Better Leaving Group<\/a><\/em><\/span>)<\/p>\n<p>How do you know if the alcohol or ether might be protonated? Look for <strong>strong acids<\/strong> such as HCl, HBr, HI, H<sub>2<\/sub>SO<sub>4<\/sub> or TsOH.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-33892\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/12-when-alcohols-are-treated-with-strong-acid-good-leaving-group-OH2-is-formed.gif\" alt=\"when alcohols are treated with strong acid good leaving group OH2 is formed\" width=\"640\" height=\"394\" \/><\/a><\/p>\n<p>The restriction that substitution and elimination reactions only happen on <em>sp<\/em><sup>3<\/sup> hybridized carbons s<strong>till applies<\/strong>, however.<\/p>\n<p>See if you can identify the carbons in each case which can undergo substitution or elimination reactions.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"34835\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"34835\"] {\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=\"34835\"] {\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=\"34835\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-34835\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-34835 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"34835\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-2s0ev\" data-id=\"2s0ev\">\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\/2425-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\/2425-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>As a side note, positively-charged sulfur, nitrogen and even phosphorus can also be good leaving groups. The leaving group in these cases are neutral amines (NR<sub>3<\/sub>) sulfides (SR<sub>2<\/sub>) or phosphines (PR<sub>3<\/sub>).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-33893\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/14-examples-of-positively-charged-leaving-groups.gif\" alt=\"examples of positively charged leaving groups\" width=\"640\" height=\"217\" \/><\/a><\/p>\n<h2><a id=\"five\"><\/a>5. Situations With Two Leaving Groups<\/h2>\n<p>There are times where you will be presented with cases where multiple good leaving groups are present, and your challenge will be to find the <strong>one\u00a0<\/strong>site on the molecule where substitution or elimination is most likely to occur.<\/p>\n<p>As we saw before, look for a good leaving group attached to an <em>sp<\/em><sup>3<\/sup> hybridized carbon.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"34836\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"34836\"] {\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=\"34836\"] {\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=\"34836\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-34836\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-34836 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"34836\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-cftun\" data-id=\"cftun\">\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\/2426-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\/2426-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>You might see other groups like OH, NH<sub>2<\/sub>, or SH in addition to the good leaving group. Those are likely <strong>nucleophiles<\/strong> that will react with the substrate via an\u00a0<strong>intramolecular\u00a0<\/strong>substitution reaction. (<span style=\"color: #993366;\"><em>See article: <a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/06\/12\/intramolecular-reactions-of-alcohols-and-ethers\/\">Intramolecular SN2 Reactions<\/a><\/em><\/span>)<\/p>\n<h2><a id=\"six\"><\/a>6. Epoxides<\/h2>\n<p>Epoxides are a special case of ethers that will undergo substitution reactions without the addition of acid. That is due to the considerable ring strain of the three-membered ring (<span style=\"color: #993366;\"><em>See article: <a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/02\/10\/opening-of-epoxide-with-base\/\">Epoxide Ring-Opening With Base<\/a><\/em><\/span>).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-33894\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/16-epoxides-can-undergo-sub-and-elim-reactions.gif\" alt=\"epoxides can undergo sub and elim reactions\" width=\"640\" height=\"376\" \/><\/a><\/p>\n<h2><a id=\"seven\"><\/a>7. Summary<\/h2>\n<p>In summary, the process for identifying where S<sub>N<\/sub>1\/S<sub>N<\/sub>2\/E1\/E2 reactions happen looks like this.<\/p>\n<ul>\n<li>Identify <strong>good leaving groups<\/strong> (such as halides, but also OTs and OMs, among others)<\/li>\n<li>&#8230; that are attached to <strong><em>sp<\/em><sup>3<\/sup> (alkyl) <\/strong>hybridized carbons.<\/li>\n<li>Additionally, alcohols and ethers can undergo S<sub>N<\/sub>1\/S<sub>N<\/sub>2\/E1\/E2 if strong acid is present.<\/li>\n<\/ul>\n<p>The next step is to identify the carbon bearing the leaving group as <strong>primary<\/strong>, <strong>secondary<\/strong>, or <strong>tertiary<\/strong>. That will help to narrow down whether the reaction will participate in an S<sub>N<\/sub>1, S<sub>N<\/sub>2, E1 or E2 reaction. More on that in the next post.<\/p>\n<p><strong>Next Post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/11\/21\/deciding-sn1sn2e1e2-1-the-substrate\/\">Deciding SN1\/SN2\/E1\/E2 &#8211; The Substrate<\/a><\/strong><\/p>\n<hr \/>\n<h2><strong><a id=\"notes\"><\/a>Notes<\/strong><\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/11\/21\/deciding-sn1sn2e1e2-1-the-substrate\/\" class=\"\"><span>Deciding SN1\/SN2\/E1\/E2 (1) \u2013 The Substrate<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/04\/12\/what-makes-a-good-leaving-group\/\" class=\"\"><span>What makes a good leaving group?<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/05\/01\/the-2-most-important-reactions-of-alkynes\/\" class=\"\"><span>Acetylides from Alkynes, And Substitution Reactions of Acetylides<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/07\/13\/the-sn1-mechanism\/\" class=\"\"><span>The SN1 Mechanism<\/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\/09\/19\/the-e1-reaction\/\" class=\"\"><span>The E1 Reaction<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/09\/27\/the-e2-mechanism\/\" class=\"\"><span>The E2 Mechanism<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/06\/16\/1-2-3-4\/\" class=\"\"><span>Primary, Secondary, Tertiary, Quaternary In Organic Chemistry<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/12\/19\/sn1-vs-e1-temperature-sn2-vs-e2\/\" class=\"\"><span>SN1 vs E1 and SN2 vs E2 : The Temperature<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/11\/30\/deciding-sn1sn2e1e2-2-the-nucleophilebase\/\" class=\"\"><span>Deciding SN1\/SN2\/E1\/E2 (2) \u2013 The Nucleophile\/Base<\/span><\/a><\/li><\/ul><\/div>\n<p><strong><a id=\"noteone\"><\/a>Note 1<\/strong> &#8211; The bond dissociation energy of fluorine in CH<sub>3<\/sub>F is about 109 kcal\/mol, even larger than the C-H bond dissociation energy (104 kcal\/mol).<\/p>\n<p><strong><a id=\"notetwo\"><\/a>Note 2<\/strong> &#8211; Despite being a weak base (the pK<sub>a<\/sub> of HCN is 9.2) the cyanide ion does not act as a good leaving group in S<sub>N<\/sub>2 reactions for reasons similar to that for fluoride ion; the C\u2013CN bond is just too strong. (<em>One <a href=\"#refone\">estimate<\/a> is that the reaction is unfavorable by about 15 kcal\/mol, which makes displacement of CN(-) very unlikely<\/em>)<\/p>\n<p>In fact, methyl cyanide, more commonly known as acetonitrile, is a commonly used polar aprotic <strong>solvent<\/strong> for S<sub>N<\/sub>2 reactions.<\/p>\n<p><strong><a id=\"notethree\"><\/a>Note 3<\/strong> &#8211; Why do SN1\/SN2\/E1\/E2 reactions happen only on alkyl halides and not on alkenyl or alkynyl halides?<\/p>\n<p>Here&#8217;s one way to look at it.<\/p>\n<p>Remember how s-orbitals are held closer to the nucleus, which is why acetylide ions are more stable than alkyl anions? You can think of alkenyl and alkynl carbons as having a great <strong>effective electronegativity\u00a0<\/strong>than alkyl carbons, which makes them &#8220;hold on&#8221; to electrons more tightly and making it more difficult for an electron pair to leave.<\/p>\n<p>So in other words, alkenyl and alkynyl carbons form stronger bonds.<\/p>\n<p>Another, related explanation has to do with the relative abilities of carbon to stabilize\u00a0<strong>positive charge<\/strong> as the amount of s-character increases.<\/p>\n<p>The E1 and S<sub>N<\/sub>1 reactions go through carbocations, whereas the S<sub>N<\/sub>2 reaction requires a partially-positive charged carbon in the transition state.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-34326\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/F1-the-sn2-reaction-proceeds-through-a-5-membered-transition-state-involving-a-partial-positive-charge.gif\" alt=\"-the sn2 reaction proceeds through a 5-membered transition state involving a partial positive charge\" width=\"640\" height=\"238\" \/><\/a><\/p>\n<p>So each of these reactions involves a transition state where the central carbon bears a partial positive charge.<\/p>\n<p>If you recall that the ability to stabilize a lone pair of electrons increases as s-character increases (sp<sup>3<\/sup> &lt; sp<sup>2<\/sup> &lt; sp ) then think of the trend in the opposite direction; the ability of a carbon to stabilize a positive charge decreases as s-character increases, as the empty orbital is held closer to the positively charged nucleus.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-34327\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/F2-the-more-s-character-the-greater-effective-electronegativity.gif\" alt=\"the more s character the greater effective electronegativity\" width=\"640\" height=\"732\" \/><\/a><\/p>\n<p><span style=\"color: #993366;\"><em>For more on the stability of carbocations, see this post on <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2011\/03\/11\/3-factors-that-stabilize-carbocations\/\">Carbocation Stability<\/a>.\u00a0<\/em><\/span><\/p>\n<p><strong><a id=\"notefour\"><\/a>Note 4<\/strong> -One exception to the &#8220;no S<sub>N<\/sub>1\/S<sub>N<\/sub>2\/E1\/E2 on <em>sp<\/em><sup>2<\/sup> hybridized carbons&#8221; is formation of alkynes from alkenyl halides via use of the extremely strong base NaNH<sub>2<\/sub>. <span style=\"color: #993366;\"><em>See article &#8211; <a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/06\/11\/alkynes-via-elimination-reactions\/\">Synthesis of Alkynes via Elimination of Alkenyl Halides<\/a><\/em><\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-34328\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/F3-example-of-e2-reaction-on-alkenyl-halide-to-give-an-alkyne.gif\" alt=\"example of e2 reaction on alkenyl halide to give an alkyne\" width=\"640\" height=\"264\" \/><\/a><\/p>\n<p><strong><a id=\"notefive\"><\/a>Note 5<\/strong>. Another exception to the &#8220;no S<sub>N<\/sub>1\/S<sub>N<\/sub>2\/E1\/E2 on <em>sp<\/em><sup>2<\/sup> hybridized carbons&#8221; is found in a reaction known as the S<sub>N<\/sub>2-prime (S<sub>N<\/sub>2&#8242;) reaction. It&#8217;s similar to the S<sub>N<\/sub>2 in that it is concerted and bimolecular, but slightly different in that the attack does not occur directly on the <em>sp<\/em><sup>2<\/sup>-hybridized alkyl halide.<\/p>\n<p>It&#8217;s not a reaction that comes up too much in introductory organic, but a good exam question.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-34329\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/F4-example-of-an-sn2-prime-reaction-exception-to-the-no-sn2-on-sp2-hybridized-carbon-principle.gif\" alt=\"example of an sn2 prime reaction exception to the no sn2 on sp2 hybridized carbon principle\" width=\"640\" height=\"461\" \/><\/a><\/p>\n<hr \/>\n<h2><strong><a id=\"quiz\"><\/a>Quiz Yourself!<\/strong><\/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\/2484-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\/2485-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\/3227-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\/3228-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\/3229-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><strong><a id=\"references\"><\/a>(Advanced) References and Further Reading<\/strong><\/h2>\n<p>In Streitweiser&#8217;s Solvolytic Displacement Reactions, page 31, :<\/p>\n<p>[According to calculations] the reaction of methyl bromide with hydroxide ion is exothermic by 16 kcal\/mol. The equivalent increase in the activation energy of the reverse reaction corresponds to a factor of 10<sup>-12\u00a0<\/sup>in rate; i.e. the rate is far too slow to be observed. Since the reactions of alkyl halides with ethoxide, phenoxide, acetate, hydrosulfide,\u00a0<strong>cyanide<\/strong>, thiosulfate and sulfite ions are all exothermic by 10-20 kcal, the reverse reactions will be slower by factors of 10<sup>-7\u00a0<\/sup>to 10<sup>-14\u00a0<\/sup>and will, therefore, not be observed except under the most exceptional conditions.&#8221;<\/p>\n<ol>\n<li><strong><a id=\"refone\"><\/a>Mechanism of ionic reactions. The heat of ionic substitution reactions<br \/>\n<\/strong>R. A. Ogg<em><strong><br \/>\n<\/strong><\/em><i>Trans. Faraday Soc.<\/i>, <strong>1935,<\/strong>31, 1385-1392<br \/>\n<strong>DOI: <a class=\"text--small\" title=\"Link to landing page via DOI\" href=\"https:\/\/doi.org\/10.1039\/TF9353101385\">10.1039\/TF9353101385<\/a><br \/>\n<\/strong>Measurement of the heats of reaction for some simple nucleophilic substitution reactions of alkyl halides with various nucleophiles.<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>Identifying Carbons Where Substitution and Elimination Reactions Can Take Place Substitution and elimination reactions need a leaving group in order for them to occur. Look <\/p>\n","protected":false},"author":1,"featured_media":33956,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1417],"tags":[472,473,201,399,841,825,502,271,279],"post_folder":[],"class_list":["post-26157","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-sn1sn2e1e2","tag-e1","tag-e2","tag-elimination","tag-hybridization","tag-leaving-group","tag-nucleophile","tag-sn1","tag-sn2","tag-substitution"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Identifying Where Substitution and Elimination Reactions Happen<\/title>\n<meta name=\"description\" content=\"How to identify where substitution (SN1 and SN2) and elimination reactions (E1 and E2) will plausibly occur by analyzing the leaving group.\" \/>\n<meta name=\"robots\" content=\"index, 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