{"id":10871,"date":"2017-07-11T17:52:57","date_gmt":"2017-07-11T21:52:57","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=10871"},"modified":"2026-04-17T21:10:51","modified_gmt":"2026-04-18T02:10:51","slug":"electrophilic-aromatic-substitution-introduction","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2017\/07\/11\/electrophilic-aromatic-substitution-introduction\/","title":{"rendered":"Electrophilic Aromatic Substitution: Introduction"},"content":{"rendered":"<p><strong>The Six Key Electrophilic Aromatic Substitution Reactions<\/strong><\/p>\n<ul>\n<li>\u00a0In <strong>electrophilic aromatic substitution <\/strong>a C-H bond is broken and a new C-E bond (E being an electrophilic atom such as Cl, Br, N&#8230;) is formed.<\/li>\n<li>There are\u00a0<strong>six<\/strong> key electrophilic aromatic substitution reactions in most introductory organic chemistry courses: <strong>chlorination<\/strong>, <strong>bromination<\/strong>, <strong>nitration<\/strong>, <strong>sulfonation<\/strong>, <strong>Friedel-Crafts alkylation<\/strong>, and <strong>Friedel-Crafts acylation<\/strong>.<\/li>\n<li>Each of these reactions requires an\u00a0<strong>acid catalyst<\/strong> to activate it so that the relatively unreactive aromatic ring will attack it.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-15833\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/0-summary-of-electrophilic-aromatic-substitution-lewis-acid-helps-form-c-e-break-c-h.gif\" alt=\"summary of electrophilic aromatic substitution lewis acid helps form c-e break c-h\" width=\"600\" height=\"351\" \/><a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2017\/07\/1-EAS-summary-e1499808658886.png\"><br \/>\n<\/a><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Alkenes Give &#8220;Addition&#8221; Products Upon Reaction With Electrophiles. So How Does Benzene Compare?<\/a><\/li>\n<li><a href=\"#two\"><span class=\"s1\">Electrophilic Aromatic Substitution<\/span><\/a><\/li>\n<li><a href=\"#three\"><span class=\"s1\"><span class=\"s1\">Lewis Acids Accelerate The Rate of Electrophilic Aromatic Substitution Reactions<\/span><\/span><\/a><\/li>\n<li><a href=\"#four\">The Key Pattern For Six Important Electrophilic Aromatic Substitution Reactions<\/a><\/li>\n<li><a href=\"#five\">Aromatic Chlorination and Bromination<\/a><\/li>\n<li><a href=\"#six\">Aromatic Nitration and Sulfonation<\/a><\/li>\n<li><a href=\"#seven\">Friedel-Crafts Alkylation and Acylation<\/a><\/li>\n<li><a href=\"#eight\">Summary: The Six Key Electrophilic Aromatic Substitution Reactions<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quiz\">Quiz Yourself!<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><strong><a id=\"one\"><\/a>1. Alkenes Give &#8220;Addition&#8221; Products Upon Reaction With Electrophiles. So How Does Benzene Compare?<\/strong><\/h2>\n<p>When we covered the reactions of <a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/01\/21\/synthesis-reactions-of-alkenes\/\">alkenes<\/a> a while back &#8211; a <em>lot<\/em> of reactions! &#8211; \u00a0we saw that the vast majority fell into the class of reactions we call\u00a0<strong>addition reactions<\/strong>. That&#8217;s where we break a (relatively weak) C-C (pi) bond and form two new single bonds to carbon. Chlorination of alkenes with Cl<sub>2<\/sub> is a classic example:<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15834\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-example-of-alkene-addition-reaction-is-chlorination-of-alkenes-form-c-cl-break-c-c-pi.gif\" alt=\"example of alkene addition reaction is chlorination of alkenes form c-cl break c-c pi\" width=\"600\" height=\"213\" \/><\/p>\n<p>Since we&#8217;re on the topic of benzene, it&#8217;s natural to wonder how well the \u00a0pi bonds in aromatic systems (like benzene) compare in reactivity to the pi bonds in alkenes, and by extension, how the reactions of aromatic compounds compare to the reactions of\u00a0alkenes.<\/p>\n<p>We&#8217;ve\u00a0seen\u00a0that benzene has <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/01\/20\/introducing-aromaticity\/\">unusual stability<\/a> (36 kcal\/mol of resonance energy) relative to what we&#8217;d expect for theoretical &#8220;cyclohexatriene&#8221;, which would certainly lead us to predict that\u00a0the pi bonds in aromatic molecules\u00a0will be\u00a0less reactive, relative to alkenes.<\/p>\n<p>You might also recall that benzene itself is unusually difficult to hydrogenate. Hydrogen (H<sub>2<\/sub>) can be made to add across most alkenes in the presence of a catalytic amount of finely divided palladium on carbon (<a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/11\/25\/palladium-on-carbon-pdc\/\">Pd\/C<\/a>), but you really need to break out the can\u00a0of <a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2017\/07\/q4nwpBa-e1499710544883.jpg\">Aldrich Brand Whup-Ass<\/a><sup>\u00ae\u00a0<\/sup>(i.e. high temperatures, high pressures of H<sub>2\u00a0<\/sub>, extended reaction times<sub>\u00a0<\/sub>) in order to successfully add H<sub>2<\/sub> to benzene, relative to &#8220;typical&#8221; alkenes.<\/p>\n<p>Knowing this, how might we expect electrophiles like Cl<sub>2<\/sub> or Br<sub>2<\/sub> to react with aromatic compounds like benzene?<\/p>\n<h2><strong><a id=\"two\"><\/a>2. Electrophilic Aromatic Substitution<\/strong><\/h2>\n<p>Our first guess might be that benzene reacts with Cl<sub>2<\/sub> to give an &#8220;addition&#8221; product like that shown below (albeit more slowly than with a &#8220;normal&#8221; alkene):<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15835\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-electrophilic-aromatic-substitution-addition-does-not-happen-with-cl2.gif\" alt=\"electrophilic aromatic substitution - addition does not happen with cl2\" width=\"600\" height=\"225\" \/><\/p>\n<p>That&#8217;s actually not the product that we observe!<\/p>\n<p>Instead, if you treat benzene with Cl<sub>2<\/sub> you will \u00a0eventually (and very slowly) obtain the following product: chlorobenzene.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15836\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-example-of-electrophilic-aromatic-substitution-of-benzene-with-cl2-gving-chlorobenzene-form-c-cl-break-c-h.gif\" alt=\"example of electrophilic aromatic substitution of benzene with cl2 gving chlorobenzene form c-cl break c-h\" width=\"600\" height=\"253\" \/><\/p>\n<p>What bonds formed and what bonds broke in this reaction?<\/p>\n<p>We formed <strong>C-Cl<\/strong> and broke <strong>C-H<\/strong> . Since the pi bonds are all intact, this is <strong>not<\/strong> an addition reaction. Instead, this is therefore a type of <strong>substitution<\/strong> reaction, where we form and break a bond on a single carbon.<\/p>\n<p>We&#8217;ve seen an example of substitution reactions before, but those were <strong>nucleophilic<\/strong> substitutions, where a nucleophile (e.g. RS<sup>&#8211;<\/sup> ) is added to an alkyl halide electrophile (e.g. R-Br), displacing a leaving group (Br<sup>\u2013<\/sup> here)\u00a0\u00a0forming a\u00a0C-Nuc bond (C-S in this case) and breaking a C-LG bond (C-Br here).<\/p>\n<p>So is the reaction of Cl<sub>2<\/sub> with benzene likewise a nucleophilic substitution reaction? <strong>No! <\/strong><\/p>\n<p>Cl<sub>2<\/sub> is an extremely poor\u00a0nucleophile, reacting as an electron-donor only with strong Lewis acids (e.g. AlCl<sub>3<\/sub>, below). \u00a0When combined with even a relatively mild\u00a0nucleophile such as the pi-bond in an alkene, it behaves as an <strong>electrophile<\/strong> (electron acceptor) as we saw in its reaction with <a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/03\/20\/alkene-addition-pattern-2-the-three-membered-ring-pathway\/\">alkenes<\/a>.<\/p>\n<p>The reaction of Cl<sub>2<\/sub> with benzene is thus called an\u00a0<strong>electrophilic aromatic substitution<\/strong>\u00a0(EAS for short):\u00a0<strong>\u00a0<\/strong><\/p>\n<ul>\n<li><strong>Electrophilic,<\/strong> because we&#8217;re adding an electron-poor species (electrophile),<\/li>\n<li>to an <strong>aromatic<\/strong> compound (benzene);<\/li>\n<li><strong>substitution<\/strong>, because we&#8217;re breaking C-H and forming C-E, where E is our electrophile (Cl in this case).<\/li>\n<\/ul>\n<h2><strong><a id=\"three\"><\/a>3. Lewis Acids Accelerate The Rate of Electrophilic Aromatic Substitution Reactions\u00a0<\/strong><\/h2>\n<p>The reaction of Cl<sub>2<\/sub>\u00a0with benzene is faster than toenail growth, but not by much\u00a0[<a href=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01134a032\">ref]<\/a>\u00a0<em>(It is, however, much faster with more electron-rich aromatics such as toluene and phenol)<\/em>. So instead of sitting around the lab for weeks waiting for a reaction to complete,\u00a0we can add a reagent that &#8220;soups up&#8221; the reactivity of Cl<sub>2<\/sub> to make it into an even better electrophile: a <strong>catalyst<\/strong>, in other words.<\/p>\n<p>Addition of a good Lewis acid like AlCl<sub>3<\/sub> or FeCl<sub>3<\/sub> does the trick.<span style=\"color: #993366;\"><em> [There are many other Lewis acids which will also do the job, but that&#8217;s a topic for when we get into the mechanism &#8211; not today]. update: <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2017\/11\/09\/electrophilic-aromatic-substitution-the-mechanism\/\">see post on mechanism<\/a><\/em><\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15837\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-reaction-of-cl2-with-benzene-is-slow-lewis-acids-greatly-accelerate-rate-of-chlorination-eg-alcl3-fecl3.gif\" alt=\"reaction of cl2 with benzene is slow lewis acids greatly accelerate rate of chlorination eg alcl3 fecl3\" width=\"600\" height=\"231\" \/><\/p>\n<p>How does this work?<\/p>\n<p>From our series on alcohols you may recall that alcohols (R\u2013OH) can be coaxed\u00a0to participate in substitution and elimination reactions\u00a0if a strong\u00a0acid is added ( forming R\u2013OH<sub>2<\/sub><sup>+<\/sup>\u00a0). \u00a0That&#8217;s because <strong><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/08\/07\/the-conjugate-acid-is-a-better-leaving-group\/\">the conjugate acid is always a better leaving group<\/a>\u00a0;<\/strong>\u00a0H<sub>2<\/sub>O is a weaker base, and thus a much better leaving group, than HO<sup>\u2013<\/sup> . \u00a0Ethanol itself will never react with NaCl to give ethyl chloride, because the resulting leaving group HO- is too strong a base relative to Cl- for the reaction to proceed to any extent. But if we convert the alcohol into its conjugate acid R-OH<sub>2<\/sub> + with a strong acid such as HCl, the reaction can then proceed, since Cl<sup>\u2013<\/sup> is displacing the much weaker base H<sub>2<\/sub>O.<\/p>\n<p>It&#8217;s\u00a0can be helpful\u00a0to think of H+ as weakening the C-O bond, and thus making the carbon attached to it a better electrophile.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15838\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-conjugate-acid-is-always-better-leaving-group-example-alcohols-substitution.gif\" alt=\"conjugate acid is always better leaving group example alcohols substitution\" width=\"600\" height=\"242\" \/><\/p>\n<p>Just as acid &#8220;primes&#8221; the carbon attached to the OH group for a subsequent reaction by converting\u00a0the hydroxyl group\u00a0into its conjugate acid, Lewis acids similarly work the same magic on Cl<sub>2\u00a0<\/sub>(and for that\u00a0matter, all the electrophilic aromatic substitution reactions we&#8217;ll be covering will involve some kind of acid catalysis).<\/p>\n<p>In the case of chlorination, the Lewis acid (AlCl<sub>3<\/sub>, below) accepts a pair of electrons from Cl<sub>2<\/sub>. This weakens the Cl\u2013Cl bond, making it into an even better electrophile.\u00a0 Attack by a nucleophile at the distal Cl will liberate not Cl- , but the even weaker base (and thus, better leaving group) AlCl<sub>4<\/sub>(-).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15839\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-reaction-of-cl2-with-lewis-acid-eg-alcl3-results-in-activating-cl-towards-electrophilic-attack.gif\" alt=\"reaction of cl2 with lewis acid eg alcl3 results in activating cl towards electrophilic attack\" width=\"600\" height=\"178\" \/><\/p>\n<p>Addition of a Lewis acid (<em>which, recall, \u00a0includes Br\u00f8nsted acids like H<sub>2<\/sub>SO<sub>4\u00a0<\/sub><\/em>) is a common thread in the six key electrophilic aromatic substitutions which are generally covered in introductory organic chemistry.<\/p>\n<h2><strong><a id=\"four\"><\/a>4. The Key Pattern For Six Important Electrophilic Aromatic Substitution Reactions<\/strong><\/h2>\n<p>In this section, we&#8217;ll\u00a0introduce these six key electrophilic aromatic substitution reactions, which group nicely into three pairs:<\/p>\n<ul>\n<li>chlorination and bromination<\/li>\n<li>nitration and sulfonylation<\/li>\n<li>Friedel-Crafts alkylation and Friedel-Crafts acylation<\/li>\n<\/ul>\n<p>We&#8217;re not going to get into the mechanisms yet.\u00a0\u00a0 The point here is just to <strong>follow what bonds form and break<\/strong>, so that you see the key pattern.<\/p>\n<p>Here it is:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15840\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-table-of-six-key-electrophilic-aromatic-substitution-reactions-chlorinatio-bromination-nitration-sulfonation-friedel-crafts.gif\" alt=\"table of six key electrophilic aromatic substitution reactions chlorinatio bromination nitration sulfonation friedel crafts\" width=\"600\" height=\"555\" \/><\/p>\n<h2><strong><a id=\"five\"><\/a>5. Chlorination and Bromination Of Aromatic Molecules<\/strong><\/h2>\n<p>We&#8217;ve seen <strong>chlorination <\/strong>(above); <strong>bromination<\/strong> is very similar. Since Br<sub>2<\/sub> by itself is not a strong enough electrophile to react with benzene at a reasonable rate, we use a Lewis acid\u00a0such as\u00a0AlBr<sub>3<\/sub> or FeBr<sub>3<\/sub> to accelerate the reaction. [Using AlBr<sub>3<\/sub>\/FeBr<sub>3<\/sub> instead of AlCl<sub>3<\/sub>\/ FeCl<sub>3<\/sub> avoids some &#8220;scrambling&#8221; of the halides, as we&#8217;ll see in a subsequent post when we get into the mechanism].<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15841\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/8-bromination-of-benzene-with-br2-and-albr3-gives-bromobenzene.gif\" alt=\"bromination of benzene with br2 and albr3 gives bromobenzene\" width=\"600\" height=\"183\" \/><\/p>\n<h2><strong><a id=\"six\"><\/a>6. Nitration and Sulfonation of Aromatic Molecules<\/strong><\/h2>\n<p><strong>Nitration<\/strong> (replacement of H with\u00a0a NO<sub>2<\/sub> group) is not a reaction we saw in our section on alkenes, but it&#8217;s a popular reaction with aromatic molecules such as benzene. This is the reaction by which methylbenzene (toluene) is converted to 2,4,6-trinitrotoluene. You&#8217;re likely more familiar with this molecule as the high explosive TNT.<\/p>\n<p>Nitration is the substitution of H with NO<sub>2<\/sub>, using nitric acid (HNO<sub>3<\/sub>) as the source of NO<sub>2<\/sub> and sulphuric acid (H<sub>2<\/sub>SO<sub>4<\/sub>) as the Lewis acid:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15842\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/9-nitration-of-benzene-with-hno3-and-h2so4-gives-nitrobenzene.gif\" alt=\"nitration of benzene with hno3 and h2so4 gives nitrobenzene\" width=\"600\" height=\"179\" \/><\/p>\n<p><strong>Sulfonation<\/strong> (replacement of H with a SO<sub>3<\/sub>H group) also turns out to be a useful reaction. It can be performed by adding sulfur trioxide (SO<sub>3<\/sub>) in the presence of sulphuric acid (H<sub>2<\/sub>SO<sub>4<\/sub>) as the Lewis acid:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15843\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/10-sulfonation-of-benzene-with-so3-and-h2so4-gives-sulfonic-acid.gif\" alt=\"sulfonation of benzene with so3 and h2so4 gives sulfonic acid\" width=\"600\" height=\"179\" \/><\/p>\n<h2><strong><a id=\"seven\"><\/a>7. Friedel-Crafts Alkylation and Acylation<\/strong><\/h2>\n<p>In the four reactions above, we observed the formation of C-Cl, C-Br, C-N and C-S.<\/p>\n<p>It&#8217;s also possible to form carbon-carbon\u00a0bonds to aromatic molecules by adding\u00a0alkyl or acyl halides in the presence of Lewis acids. These reactions are known as <a href=\"https:\/\/en.wikipedia.org\/wiki\/Friedel\u2013Crafts_reaction\">Friedel-Crafts<\/a> reactions, after their inventors (the reaction dates back to 1877).<\/p>\n<p>In<strong> Friedel-Crafts Alkylation<\/strong>, we start with an\u00a0<strong>alkyl\u00a0<\/strong>halide &#8220;R-X&#8221; such as CH<sub>3<\/sub>CH<sub>2<\/sub>Cl and then add a Lewis acid such as AlCl<sub>3<\/sub> or FeCl<sub>3<\/sub><span style=\"color: #993366;\"> [<em>there are many other Lewis acids which work, but those are the most common examples<\/em>].<\/span> \u00a0As with Cl<sub>2<\/sub>, the Lewis acid accelerates the reaction by coordinating to the halogen, weakening the C\u2013Cl bond, and making it a better leaving group and thus allowing the attached carbon to be more easily attacked by nucleophiles.\u00a0No reaction occurs without the Lewis acid.<\/p>\n<p>Note that here we form C\u2013C and break C\u2013H.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15844\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/11-friedel-crafts-alkylkation-of-benzene-with-ethyl-chloride-and-alcl3.gif\" alt=\"friedel crafts alkylkation of benzene with ethyl chloride and alcl3\" width=\"600\" height=\"208\" \/><\/p>\n<p>The <strong>Friedel-Crafts\u00a0Acylation<\/strong> is similar, but we start with an <strong>acyl<\/strong> halide. Addition of our Lewis acid results in the formation of C\u2013C and breakage of C\u2013H.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15845\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/12-friedel-crafts-acylation-of-benzene-with-acid-chloride-and-alcl3-form-c-c-break-c-h.gif\" alt=\"friedel crafts acylation of benzene with acid chloride and alcl3 form c-c break c-h\" width=\"600\" height=\"246\" \/><\/p>\n<h2><strong><a id=\"eight\"><\/a>8. Summary: The Six Key Electrophilic Aromatic Substitution Reactions<\/strong><\/h2>\n<p>We&#8217;ve shown six key electrophilic aromatic substitution reactions (chlorination, bromination, nitration, sulfonylation, and the Friedel-Crafts alkylation and acylation) and that they all involve the breakage of C-H and the formation of C-E (where &#8220;E&#8221; is the electrophile in question).<\/p>\n<p>But knowing the bonds that form and break is just the beginning.<\/p>\n<p>Here&#8217;s some questions we&#8217;d like to know the answer to:<\/p>\n<ul>\n<li>\u00a0How do substituents on benzene affect this reaction? For example, how might these reactions be affected if we performed them on methylbenzene? or phenol? or chlorobenzene?<\/li>\n<li>How do electron-donating or electron-withdrawing substituents affect the rate of the reaction?<\/li>\n<li>With benzene, only one mono-substituted product can possibly be formed. But what if we start with a mono-substituted product and do an electrophilic aromatic substitution on it? Where do the substituents end up?<\/li>\n<li>How does the reaction work? How do we explain the formation of C-E and the breakage of C-H ?<\/li>\n<li>What about other aromatic groups (beyond benzene). How do electrophilic aromatic substitution reactions on pyrrole, pyridine, naphthalene, or other groups compare?<\/li>\n<\/ul>\n<p>In the next post, we&#8217;ll discuss the first question: the effect of electron-donating and electron-withdrawing substituents. We&#8217;ll talk about <strong>activating<\/strong> and <strong>deactivating<\/strong> groups.<\/p>\n<p><strong>Next Post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/09\/26\/activating-and-deactivating-groups-in-electrophilic-aromatic-substitution\/\">Activating and Deactivating Groups<\/a><\/strong><\/p>\n<p>Thanks for reading!<\/p>\n<p>Many thanks to Matthew Knowe for assistance with this post.<\/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\/2018\/04\/18\/electrophilic-aromatic-substitutions-1-halogenation\/\" class=\"\"><span>Electrophilic Aromatic Substitutions (1) \u2013 Halogenation of Benzene<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/04\/30\/electrophilic-aromatic-substitutions-2-nitration-and-sulfonation\/\" class=\"\"><span>Electrophilic Aromatic Substitutions (2) \u2013 Nitration and Sulfonation<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/05\/17\/friedel-crafts-alkylation-acylation\/\" class=\"\"><span>EAS Reactions (3) \u2013 Friedel-Crafts Acylation and Friedel-Crafts Alkylation<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/11\/09\/electrophilic-aromatic-substitution-the-mechanism\/\" class=\"\"><span>Electrophilic Aromatic Substitution \u2013 The Mechanism<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/02\/02\/understanding-ortho-para-meta-directors\/\" class=\"\"><span>Understanding Ortho, Para, and Meta Directors<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/03\/05\/why-are-halogens-ortho-para-directors\/\" class=\"\"><span>Why are halogens ortho- para- directors?<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/organic-chemistry-practice-problems\/aromatic-reactions-and-synthesis-practice\/\" class=\"\"><span>Aromatic Reactions and Synthesis Practice<\/span><\/a><\/li><\/ul><\/div>\n<hr \/>\n<h2><a id=\"quiz\"><\/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\/0515-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\/3111-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\/3112-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\/0516-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\/0517-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>The Six Key Electrophilic Aromatic Substitution Reactions \u00a0In electrophilic aromatic substitution a C-H bond is broken and a new C-E bond (E being an electrophilic <\/p>\n","protected":false},"author":1,"featured_media":15833,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1297],"tags":[796,310,319,321,1231,1232],"post_folder":[],"class_list":["post-10871","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-aromatic-reactions","tag-bromination","tag-chlorination","tag-electrophilic-aromatic-substitution","tag-friedel-crafts","tag-nitration","tag-sulfonylation"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Electrophilic Aromatic Substitution: The Six Key Reactions<\/title>\n<meta name=\"description\" content=\"Introduction to the six key reactions of electrophilic aromatic substitution: chlorination, bromination, nitration, sulfonation, FC alkylation &amp; acylation\" \/>\n<meta name=\"robots\" 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