{"id":48904,"date":"2023-09-30T09:05:54","date_gmt":"2023-09-30T03:20:54","guid":{"rendered":"https:\/\/thechemistrynotes.com\/?p=48904"},"modified":"2023-09-30T09:05:57","modified_gmt":"2023-09-30T03:20:57","slug":"electrophilic-substitution-reaction","status":"publish","type":"post","link":"https:\/\/thechemistrynotes.com\/electrophilic-substitution-reaction\/","title":{"rendered":"Electrophilic Substitution Reaction: Mechanism, Types, Applications"},"content":{"rendered":"\n<figure class=\"wp-block-image size-large\"><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"536\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Electrophilic-Substitution-Reaction-1024x536.jpg\" alt=\"Electrophilic Substitution Reaction\" class=\"wp-image-48912\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Electrophilic-Substitution-Reaction-1024x536.jpg 1024w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Electrophilic-Substitution-Reaction-300x157.jpg 300w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Electrophilic-Substitution-Reaction-768x402.jpg 768w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Electrophilic-Substitution-Reaction.jpg 1205w\" sizes=\"(max-width: 1024px) 100vw, 1024px\" \/><\/figure>\n\n\n\n<p>An electrophilic substitution reaction is a chemical process in which an electrophile replaces the functional group connected to a molecule. The displaced functional group is usually a hydrogen atom.<\/p>\n\n\n\n<p>The primary distinction between nucleophilic and electrophilic substitution reactions is that the former requires the displacement of a leaving group by a nucleophile, whereas the latter involves the displacement of a functional group by an electrophile.<\/p>\n\n\n\n<div id=\"ez-toc-container\" class=\"ez-toc-v2_0_65 counter-hierarchy ez-toc-counter ez-toc-custom ez-toc-container-direction\">\n<div class=\"ez-toc-title-container\">\n<p class=\"ez-toc-title \" >Table of Contents<\/p>\n<span class=\"ez-toc-title-toggle\"><a href=\"#\" class=\"ez-toc-pull-right ez-toc-btn ez-toc-btn-xs ez-toc-btn-default ez-toc-toggle\" aria-label=\"Toggle Table of Content\"><span class=\"ez-toc-js-icon-con\"><span class=\"\"><span class=\"eztoc-hide\" style=\"display:none;\">Toggle<\/span><span class=\"ez-toc-icon-toggle-span\"><svg style=\"fill: #0a0a0a;color:#0a0a0a\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" class=\"list-377408\" width=\"20px\" height=\"20px\" viewBox=\"0 0 24 24\" fill=\"none\"><path d=\"M6 6H4v2h2V6zm14 0H8v2h12V6zM4 11h2v2H4v-2zm16 0H8v2h12v-2zM4 16h2v2H4v-2zm16 0H8v2h12v-2z\" fill=\"currentColor\"><\/path><\/svg><svg style=\"fill: #0a0a0a;color:#0a0a0a\" class=\"arrow-unsorted-368013\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" width=\"10px\" height=\"10px\" viewBox=\"0 0 24 24\" version=\"1.2\" baseProfile=\"tiny\"><path d=\"M18.2 9.3l-6.2-6.3-6.2 6.3c-.2.2-.3.4-.3.7s.1.5.3.7c.2.2.4.3.7.3h11c.3 0 .5-.1.7-.3.2-.2.3-.5.3-.7s-.1-.5-.3-.7zM5.8 14.7l6.2 6.3 6.2-6.3c.2-.2.3-.5.3-.7s-.1-.5-.3-.7c-.2-.2-.4-.3-.7-.3h-11c-.3 0-.5.1-.7.3-.2.2-.3.5-.3.7s.1.5.3.7z\"\/><\/svg><\/span><\/span><\/span><\/a><\/span><\/div>\n<nav><ul class='ez-toc-list ez-toc-list-level-1 ' ><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-1\" href=\"https:\/\/thechemistrynotes.com\/electrophilic-substitution-reaction\/#mechanism-of-electrophilic-substitution-reaction\" title=\"Mechanism of electrophilic substitution reaction\">Mechanism of electrophilic substitution reaction<\/a><ul class='ez-toc-list-level-3' ><li class='ez-toc-heading-level-3'><a class=\"ez-toc-link ez-toc-heading-2\" href=\"https:\/\/thechemistrynotes.com\/electrophilic-substitution-reaction\/#generation-of-electrophile\" title=\"Generation of electrophile\">Generation of electrophile<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-3'><a class=\"ez-toc-link ez-toc-heading-3\" href=\"https:\/\/thechemistrynotes.com\/electrophilic-substitution-reaction\/#formation-of-intermediate\" title=\"Formation of intermediate\">Formation of intermediate<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-3'><a class=\"ez-toc-link ez-toc-heading-4\" href=\"https:\/\/thechemistrynotes.com\/electrophilic-substitution-reaction\/#abstraction-of-hydrogen-from-intermediate\" title=\"Abstraction of hydrogen from intermediate\">Abstraction of hydrogen from intermediate<\/a><\/li><\/ul><\/li><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-5\" href=\"https:\/\/thechemistrynotes.com\/electrophilic-substitution-reaction\/#types-of-electrophilic-substitution-reaction\" title=\"Types of electrophilic substitution reaction\">Types of electrophilic substitution reaction<\/a><ul class='ez-toc-list-level-3' ><li class='ez-toc-heading-level-3'><a class=\"ez-toc-link ez-toc-heading-6\" href=\"https:\/\/thechemistrynotes.com\/electrophilic-substitution-reaction\/#electrophilic-aliphatic-substitution-reaction\" title=\"Electrophilic aliphatic substitution reaction\">Electrophilic aliphatic substitution reaction<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-3'><a class=\"ez-toc-link ez-toc-heading-7\" href=\"https:\/\/thechemistrynotes.com\/electrophilic-substitution-reaction\/#electrophilic-aromatic-substitution-reaction\" title=\"Electrophilic aromatic substitution reaction\">Electrophilic aromatic substitution reaction<\/a><\/li><\/ul><\/li><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-8\" href=\"https:\/\/thechemistrynotes.com\/electrophilic-substitution-reaction\/#importance-of-electrophilic-substitution-reactions\" title=\"Importance of electrophilic substitution reactions\">Importance of electrophilic substitution reactions<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-9\" href=\"https:\/\/thechemistrynotes.com\/electrophilic-substitution-reaction\/#references\" title=\"References\">References<\/a><\/li><\/ul><\/nav><\/div>\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"mechanism-of-electrophilic-substitution-reaction\"><\/span><strong>Mechanism of electrophilic substitution reaction<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<p>Electrophilic substitution reaction mainly involves three steps:<\/p>\n\n\n\n<ol type=\"1\">\n<li>Generation of electrophile<\/li>\n\n\n\n<li>Formation of intermediate<\/li>\n\n\n\n<li>Abstraction of hydrogen from intermediate<\/li>\n<\/ol>\n\n\n\n<h3 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"generation-of-electrophile\"><\/span><strong>Generation of electrophile<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h3>\n\n\n\n<p>Anhydrous aluminum chloride is a very helpful Lewis acid in the production of electrophiles for\u00a0aromatic ring chlorination, alkylation, and acylation. Electrophiles are formed in the presence of Lewis acid. The attacking reagent&#8217;s electron pair is accepted by the Lewis acid. Cl<sup>+<\/sup>, R<sup>+<\/sup>, and RC<sup>+<\/sup>O electrophiles are generated from the conjunction of anhydrous aluminum chloride with the attacking reagent.<\/p>\n\n\n<div class=\"wp-block-image\">\n<figure class=\"aligncenter size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"620\" height=\"143\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-88.png\" alt=\"\" class=\"wp-image-48907\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-88.png 620w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-88-300x69.png 300w\" sizes=\"(max-width: 620px) 100vw, 620px\" \/><\/figure><\/div>\n\n\n<h3 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"formation-of-intermediate\"><\/span><strong>Formation of intermediate<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h3>\n\n\n\n<p>When an electrophile attacks an aromatic ring, an arenium ion or sigma complex is formed. Another carbon in this arenium ion has gone through sp3 hybridization. This arenium ion achieves stability in a resonance configuration. Because electron delocalization occurs at the sp3 hybridized\u00a0carbon,&#8217; the aromatic property of the sigma\u00a0complex or intermediate ion&#8217; is lost.<\/p>\n\n\n\n<figure class=\"wp-block-image size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"972\" height=\"175\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-89.png\" alt=\"\" class=\"wp-image-48908\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-89.png 972w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-89-300x54.png 300w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-89-768x138.png 768w\" sizes=\"(max-width: 972px) 100vw, 972px\" \/><\/figure>\n\n\n\n<h3 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"abstraction-of-hydrogen-from-intermediate\"><\/span><strong>Abstraction of hydrogen from intermediate<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h3>\n\n\n\n<p>The sigma complex releases a proton from the sp3 hybridized carbon when it is attacked by AlCl4 to\u00a0restore the aromatic characteristic. As a result, the electrophile replaces the hydrogen ion within the benzene ring. Because the concept of electrophilic substitution has been applied in the majority of organic name reactions, it is an extremely important reaction in organic chemistry.<\/p>\n\n\n<div class=\"wp-block-image\">\n<figure class=\"aligncenter size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"803\" height=\"173\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-91.png\" alt=\"\" class=\"wp-image-48910\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-91.png 803w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-91-300x65.png 300w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-91-768x165.png 768w\" sizes=\"(max-width: 803px) 100vw, 803px\" \/><\/figure><\/div>\n\n\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"types-of-electrophilic-substitution-reaction\"><\/span><strong>Types of electrophilic substitution reaction<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<p>There are two types of electrophilic substitution reaction processes. They are:<\/p>\n\n\n\n<ol type=\"1\">\n<li>Electrophilic aliphatic substitution reaction<\/li>\n\n\n\n<li>Electrophilic Aromatic substitution reaction<\/li>\n<\/ol>\n\n\n\n<h3 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"electrophilic-aliphatic-substitution-reaction\"><\/span><strong>Electrophilic aliphatic substitution reaction<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h3>\n\n\n\n<p>&#8216;Electrophilic aliphatic substitution reactions&#8217; occur when an electrophile displaces a functional group in an aliphatic molecule. In these reactions, the electrophile attacks the aliphatic molecule, resulting in a 180\u00b0 inversion. The electrophilic substitution in aliphatic compounds is identical to the nucleophilic substitution in aliphatic compounds, except that an electrophile replaces a functional group rather than a nucleophile. The two basic electrophilic substitutions are SE<sub>2 <\/sub>(substitution electrophilic bimolecular) and SE<sub>i<\/sub> (substitution electrophilic internal) processes.<\/p>\n\n\n\n<h4 class=\"wp-block-heading\"><strong>Substitution electrophilic bimolecular(SE<sub>2<\/sub>)<\/strong><\/h4>\n\n\n\n<p>Bimolecular electrophilic substitution (SE2) reactions are essentially chemical changes in which a stronger electrophile displaces a weaker electrophile in an aliphatic substrate.<\/p>\n\n\n\n<p>Except for the form of attack, this technique is very similar to the SN<sub>2<\/sub> route. Due to its inter-cloud repulsion with the leaving group, a stronger nucleophile replaces a weaker one via the backside attack in the SN<sub>2<\/sub> mechanism; however, in the SE<sub>2<\/sub> route, the attacking electrophile may come from the front as well as the backside because it is only using its vacant orbital towards substrates, causing little to no repulsion. So, depending on the front and rear attacks, the SE<sub>2<\/sub> mechanism can be separated into SE<sub>2<\/sub>-front and SE<sub>2<\/sub>-back.<\/p>\n\n\n\n<h4 class=\"wp-block-heading\"><strong>Substitution electrophilic internal (SE<sub>i<\/sub>)<\/strong><\/h4>\n\n\n\n<p>Internal electrophilic substitution reactions are chemical changes that occur when a stronger electrophile displaces a weaker one in an aliphatic substrate by facilitating its departure.<\/p>\n\n\n\n<p>Except for the form of attack, this technique is extremely similar to the SN2 route. Due to its inter-cloud repulsion with the leaving group, a stronger nucleophile replaces a weaker one via the backside attack in the SN2 mechanism; whereas, in the SEI pathway, the attacking electrophile comes from the front and facilitates the leaving group&#8217;s departure by establishing a bond&nbsp;with it.<\/p>\n\n\n\n<p>Examples of electrophilic aliphatic substitution reactions are:<\/p>\n\n\n\n<ul>\n<li>Nitrosation<\/li>\n\n\n\n<li><a href=\"https:\/\/thechemistrynotes.com\/aldehyde-ketone\/\">Ketone<\/a> halogenation<\/li>\n\n\n\n<li>Carbene insertion into a carbon-hydrogen bond<\/li>\n\n\n\n<li>Tautomerism of keto-enol<\/li>\n\n\n\n<li>Diazonium fusion (aliphatic)<\/li>\n<\/ul>\n\n\n\n<h3 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"electrophilic-aromatic-substitution-reaction\"><\/span><strong>Electrophilic aromatic substitution reaction<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h3>\n\n\n\n<p>An aromatic compound undergoes an electrophilic substitution reaction when the aromatic ring is substituted or displaced by an electrophile. In such reactions, the aromaticity of molecules is retained. Examples of electrophilic aromatic substitution reactions include sulfonation, Friedel-Crafts reactions, and nitration in aromatic compounds.<\/p>\n\n\n\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"importance-of-electrophilic-substitution-reactions\"><\/span><strong>Importance of electrophilic substitution reactions<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<ul>\n<li>One of the most important procedures in synthetic organic chemistry is electrophilic aromatic substitution.<\/li>\n\n\n\n<li>These reactions produce a significant intermediate that can be used as a precursor in the manufacture of industrial, agrochemical, and medicinal products.<\/li>\n\n\n\n<li>In mild conditions, zeolites can benefit from halogenation, alkylation, para-regioselective nitration, acylation, and methanesulfonyl reaction pathways. They are also typically simple to filter out of the reaction mixture and then revitalize by heating, enabling recurrent use with nearly the same productivity and selectivity as samples.<\/li>\n<\/ul>\n\n\n\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"references\"><\/span><strong>References<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<ul>\n<li>https:\/\/www.dalalinstitute.com\/wp-content\/uploads\/Books\/A-Textbook-of-Organic-Chemistry-Volume-1\/ATOOCV1-7-0-Aliphatic-Electrophilic-Substitution.pdf<\/li>\n\n\n\n<li>https:\/\/byjus.com\/chemistry\/electrophilic-substitution-reaction-mechanism\/<\/li>\n\n\n\n<li>https:\/\/www.chemistrylearner.com\/electrophilic-substitution.html<\/li>\n\n\n\n<li>https:\/\/collegedunia.com\/exams\/electrophilic-substitution-definition-reaction-and-mechanism-chemistry-articleid-1947<\/li>\n\n\n\n<li>https:\/\/unacademy.com\/content\/jee\/study-material\/chemistry\/electrophilic-substitution-reaction\/<\/li>\n<\/ul>\n","protected":false},"excerpt":{"rendered":"<p>An electrophilic substitution reaction is a chemical process in which an electrophile replaces the functional group connected to a molecule. The displaced functional group is usually a hydrogen atom. The &#8230; <a title=\"Electrophilic Substitution Reaction: Mechanism, Types, Applications\" class=\"read-more\" href=\"https:\/\/thechemistrynotes.com\/electrophilic-substitution-reaction\/\" aria-label=\"Read more about Electrophilic Substitution Reaction: Mechanism, Types, Applications\">Read more<\/a><\/p>\n","protected":false},"author":4,"featured_media":48912,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[21],"tags":[2924,2921,2922,2923],"_links":{"self":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts\/48904"}],"collection":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/users\/4"}],"replies":[{"embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/comments?post=48904"}],"version-history":[{"count":3,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts\/48904\/revisions"}],"predecessor-version":[{"id":48913,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts\/48904\/revisions\/48913"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/media\/48912"}],"wp:attachment":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/media?parent=48904"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/categories?post=48904"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/tags?post=48904"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}