{"id":5295,"date":"2012-06-27T20:30:41","date_gmt":"2012-06-27T20:30:41","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=5295"},"modified":"2025-11-20T12:49:52","modified_gmt":"2025-11-20T18:49:52","slug":"two-types-of-substitution-reactions","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2012\/06\/27\/two-types-of-substitution-reactions\/","title":{"rendered":"Two Types of Nucleophilic Substitution Reactions"},"content":{"rendered":"<p><strong>Comparing Two Nucleophilic Substitution Reactions That Clearly Have Different Mechanisms<\/strong><\/p>\n<p>Experiments tell us that\u00a0<strong>nucleophilic substitution reactions\u00a0<\/strong>generally fall into\u00a0<strong>two main groups:<\/strong><\/p>\n<p>In one group:<\/p>\n<ul>\n<li>The reaction rate depends\u00a0<strong>only\u00a0<\/strong>on the concentration of substrate (alkyl halide) and not on the concentration of nucleophile<\/li>\n<li>The reaction rate is\u00a0<strong>fastest<\/strong> for\u00a0<strong>tertiary\u00a0<\/strong>alkyl halides and\u00a0<strong>slowest<\/strong> for\u00a0<strong>primary\u00a0<\/strong>(and methyl) alkyl halides<\/li>\n<li>The\u00a0<strong>stereochemistry\u00a0<\/strong>of the product, relative to the starting material, is a mixture of\u00a0<strong>retention\u00a0<\/strong>and\u00a0<strong>inversion<\/strong><\/li>\n<\/ul>\n<p>In a second group:<\/p>\n<ul>\n<li>The reaction rate depends\u00a0<strong>both<\/strong> on the concentration of substrate and nucleophile<\/li>\n<li>The reaction rate is\u00a0<strong>fastest\u00a0<\/strong>for\u00a0<strong>primary\u00a0<\/strong>alkyl halides and\u00a0<strong>slowest<\/strong> for\u00a0<strong>tertiary\u00a0<\/strong>alkyl halides<\/li>\n<li>The\u00a0<strong>stereochemistry\u00a0<\/strong>of the product shows\u00a0<strong>inversion of configuration\u00a0<\/strong>relative to the stereochemistry of the starting material<strong>.\u00a0<\/strong><\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-37732\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/10\/0-Summary-Two-Types-of-Nucleophilic-Substitution-Reactions.gif\" alt=\"Summary Two Types of Nucleophilic Substitution Reactions\" width=\"640\" height=\"506\" \/><\/a><\/p>\n<p>As we will see, this experimental data points to the fact that there are\u00a0<strong>two distinct mechanisms\u00a0<\/strong>for substitution reactions, which we will identify as<strong> S<sub>N<\/sub>1<\/strong> (<em>nucleophilic substitution, <strong>unimolecular<\/strong> rate-determining step<\/em>) and<strong> S<sub>N<\/sub>2<\/strong> (<em>nucleophilic substitution, <strong>bimolecular<\/strong> rate-determining step<\/em>).<\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">How Two Nucleophilic Substitution Reactions Vary According To Substrate (Methyl, Primary, Secondary, Tertiary Alkyl Halides)<\/a><\/li>\n<li><a href=\"#two\">How Two Nucleophilic Substitution Reactions Vary According To Rate Laws (First Order versus Second Order)<\/a><\/li>\n<li><a href=\"#three\">How Two Substitution Reactions Vary According To Stereochemistry (Inversion versus Retention + Inversion)<\/a><\/li>\n<li><a href=\"#four\">Given This Information, Come Up With A Hypothesis For Two Substitution Mechanisms<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quizzes\">Quiz Yourself!<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><strong><a id=\"one\"><\/a>1. How Two Nucleophilic Substitution Reactions Vary According To Substrate (Methyl, Primary, Secondary, Tertiary Alkyl Halides)<\/strong><\/h2>\n<p>The <strong>rate<\/strong> of a reaction is something we can readily measure. Some substitution reactions show a definite pattern as we move from <strong>primary<\/strong> substrates (substrate here being an alkyl halide) to <strong>tertiary<\/strong> substrates.<\/p>\n<p>In the first reaction, the primary alkyl halide gives a faster reaction under otherwise identical conditions than does the tertiary alkyl halide.<\/p>\n<p>However, there are substitution reactions that serve as a counterpoint. In the second example, it is the <em>tertiary <\/em>substrate that reacts fastest, followed by the primary substrate.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-14801\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-comparing-substitution-reactions-primary-versus-tertiary-can-be-faster-depending-on-nucleophile.gif\" alt=\"comparing substitution reactions primary versus tertiary can be faster depending on nucleophile\" width=\"600\" height=\"387\" \/><\/p>\n<p>Interesting!<\/p>\n<h2><strong><a id=\"two\"><\/a>2. How Two Nucleophilic Substitution Reactions Vary According To Rate Laws (First Order versus Second Order)<\/strong><\/h2>\n<p>Measuring the rate also lets us test how dependent it is upon the <strong>concentrations<\/strong> of the various reactions. We can try seeing what happens to the rate when we double or quadruple <span style=\"color: #993366;\"><em>(or octuple &#8211; is that a word?)<\/em><\/span> the concentration of the nucleophile or substrate.<\/p>\n<p>In the first reaction, the rate increases <strong>linearly<\/strong> as we increase the <strong>concentration<\/strong> of either substrate or nucleophile. That is, if we keep the concentration of substrate constant, and <strong>double<\/strong> the concentration of nucleophile, we will <strong>double<\/strong> the rate.<\/p>\n<p>However, the rate of the second reaction is only sensitive to the concentration of substrate. No matter how much we increase (or decrease) the concentration of nucleophile, the rate does not change!<\/p>\n<h2><img decoding=\"async\" class=\"alignnone wp-image-14802\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-comparing-nucleophilic-substitution-reactions-rate-law-of-sn1-is-unimolecular-rate-law-of-sn2-is-bimolecular.gif\" alt=\"comparing nucleophilic substitution reactions rate law of sn1 is unimolecular rate law of sn2 is bimolecular\" width=\"600\" height=\"626\" \/><a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2012\/06\/2-rate-laws.png\"><br \/>\n<\/a><strong><a id=\"three\"><\/a>3. How Two Substitution Reactions Vary According To Stereochemistry (Inversion versus Retention + Inversion)<\/strong><\/h2>\n<p>It&#8217;s also possible to measure the <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/02\/07\/optical-rotation-optical-activity-and-specific-rotation\/\">optical rotation<\/a> of a molecule, which is a property of its stereochemistry. As techniques became more refined, we&#8217;ve been able to isolate and work with enantiomerically pure compounds.<\/p>\n<p>Interesting observation: if you start with a single enantiomer in the top reaction, you obtain a single enantiomer &#8211; except that the absolute configuration has been reversed!<\/p>\n<p>This is called inversion of configuration.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-14803\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-stereochemistry-in-substitution-reactions-some-have-inversion-some-have-retention-plus-inversion.gif\" alt=\"stereochemistry in substitution reactions some have inversion some have retention plus inversion\" width=\"600\" height=\"351\" \/><\/p>\n<p>On the other hand, in the bottom reaction, starting with a single enantiomer we tend to get a mixture of retention <strong>and<\/strong> inversion.<\/p>\n<p><span style=\"color: #993366;\"><em>(If the amount of retention and inversion is equal, we call this &#8220;racemization&#8221;. Sometimes they&#8217;re not exactly equal).<\/em><\/span><\/p>\n<h2><strong><a id=\"four\"><\/a>4. Given This Information, Come Up With A Hypothesis For Two Substitution Mechanisms<\/strong><\/h2>\n<p>So given the data that we have (and these are just a few out of countless examples), how do we come up with hypotheses for how these reactions work?<\/p>\n<p>They have to explain:<\/p>\n<ol>\n<li>How the bonds form and how they break<\/li>\n<li>The dependence on type of substrate<\/li>\n<li>The dependence on concentration<\/li>\n<li>The observations of stereochemistry<\/li>\n<\/ol>\n<p>These hypotheses are called <strong>mechanisms<\/strong>. Think about how each of these two reactions could potentially work. Then, in the next post, we&#8217;ll go through the first type of substitution reaction.<\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/07\/04\/the-sn2-mechanism\/\"><strong>Next Post: The SN2 Mechanism<\/strong><\/a><\/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\/2012\/08\/08\/comparing-the-sn1-and-sn2-reactions\/\" class=\"\"><span>Comparing the SN1 and SN2 Reactions<\/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\/2023\/01\/18\/where-will-substitution-elimination-reactions-occur\/\" class=\"\"><span>Identifying Where Substitution and Elimination Reactions Happen<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/05\/01\/acetylide-formation-alkylation\/\" class=\"\"><span>Acetylides from Alkynes, And Substitution Reactions of Acetylides<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/11\/09\/e1-reaction-rearrangement\/\" class=\"\"><span>Elimination (E1) Reactions With Rearrangements<\/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><\/ul><\/div>\n<p><strong><a id=\"noteone\"><\/a>Note 1. <\/strong>[The initial introduction to this article] . Chemistry is an experimental science. There is no great <a href=\"http:\/\/en.wikipedia.org\/wiki\/Srinivasa_Ramanujan\">Ramanujan<\/a> of our discipline, who, starting with a simple set of premises, could derive and predict all of the depth and variety of modern chemistry. No, it is much messier than that.<\/p>\n<p>Chemists have to actively interrogate Nature to learn her secrets. We add substances together and make observations. Given enough reproducible observations, across a number of different variables, we start to see patterns. And once those patterns become apparent, we can then make hypotheses, and test them.\u00a0 The hypotheses that survive experimental testing eventually become known as &#8220;laws&#8221;, although they are really just very strong theories that have not been falsified.<\/p>\n<p>This is just a long way of saying that the data comes first, and hypotheses come second &#8211; in the act of looking \u00a0backwards. Since we&#8217;re talking about substitution reactions, let&#8217;s go through some interesting, seemingly contradictory <strong>data<\/strong> about substitution reactions that have been recorded, and then (in future posts) we can look backwards and talk about what they mean.<\/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\/3569-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\/3570-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\/3571-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\/3572-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\/3573-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","protected":false},"excerpt":{"rendered":"<p>Comparing Two Nucleophilic Substitution Reactions That Clearly Have Different Mechanisms Experiments tell us that\u00a0nucleophilic substitution reactions\u00a0generally fall into\u00a0two main groups: In one group: The reaction <\/p>\n","protected":false},"author":1,"featured_media":37732,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1414],"tags":[842,841,825,608,843,502,271,279,606],"post_folder":[],"class_list":["post-5295","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-substitution-reactions","tag-alkyl-halide","tag-leaving-group","tag-nucleophile","tag-primary","tag-rate-law","tag-sn1","tag-sn2","tag-substitution","tag-tertiary"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - 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