{"id":11246,"date":"2018-01-29T07:00:50","date_gmt":"2018-01-29T13:00:50","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=11246"},"modified":"2025-06-12T11:17:16","modified_gmt":"2025-06-12T16:17:16","slug":"ortho-para-and-meta-directors-in-electrophilic-aromatic-substitution","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2018\/01\/29\/ortho-para-and-meta-directors-in-electrophilic-aromatic-substitution\/","title":{"rendered":"Ortho-, Para- and Meta- Directors in Electrophilic Aromatic Substitution"},"content":{"rendered":"<p><strong>Two Important Reaction Patterns: <em>Ortho- , Para-<\/em> Directors and <em>Meta-<\/em> Directors<\/strong><\/p>\n<p>It&#8217;s one thing to learn about electrophilic aromatic substitution reactions of benzene itself.<\/p>\n<p>But once you move toward substituted benzenes, that&#8217;s when things start getting<em> really<\/em> interesting.<\/p>\n<p>Today we&#8217;ll describe the two main patterns by which various substituents &#8220;<strong>direct<\/strong>&#8221; electrophilic aromatic substitution.<\/p>\n<ul>\n<li>In <strong>one<\/strong> pattern, substituents direct the reaction to give either the &#8220;<em>ortho<\/em>&#8221; (1,2) or &#8220;<em>para<\/em>&#8221; (1,4) product, with a slight preference for &#8220;para&#8221; due to less steric hindrance.<\/li>\n<li>In the <strong>second<\/strong> pattern, a different family of substituents direct the reaction to give primarily the &#8220;<em>meta<\/em>&#8221; (1,3) product.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-30114\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2018\/01\/0-summary-ortho-meta-para-directors-for-electrophilic-aromatic-substitution.gif\" alt=\"summary-ortho meta para directors for electrophilic aromatic substitution\" width=\"640\" height=\"646\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">\u00a0o<em>rtho-<\/em>, <em>p<\/em><em>ara-<\/em> Directors<\/a><\/li>\n<li><a href=\"#two\"><i>meta-<\/i> Directors<\/a><\/li>\n<li><a href=\"#three\">How Well Do &#8220;<i>ortho-, para<\/i>&#8221; And &#8220;<i>meta<\/i>&#8220;- Directors Correlate With &#8220;Activating&#8221; and &#8220;Deactivating&#8221; Groups?<\/a><\/li>\n<li><a href=\"#four\">The Key To Understanding\u00a0<i>ortho-, para-\u00a0<\/i>Directors And\u00a0<i>meta-<\/i> Directors Is To Understand The Stability of The Carbocation Intermediate<\/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. o<em>rtho-<\/em>, <em>p<\/em><em>ara-<\/em>\u00a0Directors<\/strong><\/h2>\n<p>Here&#8217;s a fascinating observation.<\/p>\n<p>Start with a monosubstituted benzene. Then perform some kind of electrophilic aromatic substitution\u00a0 (nitration, halogenation, sulfonation &#8211; turns out it doesn&#8217;t matter).<\/p>\n<p><strong>Two important reaction patterns are observed.\u00a0<\/strong><\/p>\n<p>It&#8217;s important to note that these two patterns are wholly a function of the <strong>substituent<\/strong> and not the reaction itself.<\/p>\n<p>In one pattern, <em>ortho-<\/em>\u00a0and <em>para<\/em>&#8211; products dominate, and the <em>meta-<\/em> product is an extremely minor byproduct.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-40900\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/06\/1-what-is-an-ortho-para-director-gives-mostly-ortho-and-para-products-in-electrophilic-aromatic-substitution-with-examples-edit.gif\" alt=\"what is an ortho para director - gives mostly ortho and para products in electrophilic aromatic substitution with examples-edit\" width=\"640\" height=\"484\" \/><\/a><\/p>\n<p>Substituents which lead to this result are called, &#8220;<em>ortho-,\u00a0<\/em><em>para-\u00a0<\/em>directors&#8221;.\u00a0Examples of ortho-,\u00a0<em>para<\/em>&#8211; directors are hydroxyl groups, ethers, amines, alkyl groups, thiols, and halogens.<\/p>\n<p>Here&#8217;s a concrete example: the nitration of methoxybenzene (also known as anisole).<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15871\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-electrophilic-aromatic-substitution-of-anisole-showing-it-to-be-ortho-para-director-example.gif\" alt=\"electrophilic aromatic substitution of anisole showing it to be ortho para director example\" width=\"600\" height=\"290\" \/><\/p>\n<p><em>ortho-\u00a0<\/em>and<em>\u00a0<\/em><em>para-\u00a0<\/em>products dominate, while\u00a0<em>meta<\/em>&#8211; products comprise less than 3%.<\/p>\n<h2><a id=\"two\"><\/a>2.\u00a0<em>meta-<\/em> Directors<\/h2>\n<p>In the second pattern, the\u00a0<em>meta<\/em>&#8211; product dominates, and the\u00a0<em>ortho-\u00a0<\/em>and\u00a0<em>para<\/em>&#8211; products are minor.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-40901\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/06\/3-what-is-a-meta-director-substituent-which-gives-mostly-meta-product-in-electrophilic-aromatic-substitution-with-example-edit.gif\" alt=\"what is a meta director - substituent which gives mostly meta product in electrophilic aromatic substitution with example-edit\" width=\"640\" height=\"493\" \/><\/a><\/p>\n<p>We call the substituents which lead to this result &#8220;<em>meta-\u00a0<\/em>directors&#8221;. Examples of <em>meta<\/em>&#8211; directors include nitriles, carbonyl compounds (such as aldehydes, ketones, and esters), sulfones, electron-deficient alkyl groups, nitro groups, and alkylammoniums.<\/p>\n<p>Specific example: nitration of trifluoromethylbenzene gives the <em>meta\u00a0<\/em>product in about 90% yield. (Compare that to the case of anisole, above, where nitration resulted in a &lt;5% yield of the\u00a0<em>meta<\/em> product. )\u00a0 Barnacle<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15873\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-electrophilic-aromatic-substitution-of-trifluoromethylbenzene-gives-mostly-meta-products.gif\" alt=\"electrophilic aromatic substitution of trifluoromethylbenzene gives mostly meta products\" width=\"600\" height=\"306\" \/><\/p>\n<h2><strong><a id=\"three\"><\/a>3. How Well Do &#8220;<em>ortho-, para<\/em>&#8221; And &#8220;<em>meta<\/em>&#8220;- Directors Correlate With &#8220;Activating&#8221; and &#8220;Deactivating&#8221; Groups?<\/strong><\/h2>\n<p>What factors could be in play here? How do\u00a0<em>ortho-, para-\u00a0<\/em>and\u00a0<em>meta<\/em>&#8211; directors differ, and how could this difference affect the product distribution?<\/p>\n<p>Great question.<\/p>\n<p>One aspect we&#8217;ve covered previously is the concept of <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/09\/26\/activating-and-deactivating-groups-in-electrophilic-aromatic-substitution\/\">&#8220;activating&#8221; and &#8220;deactivating&#8221; groups<\/a>.<\/p>\n<p>We said that<\/p>\n<ul>\n<li><strong>Activating\u00a0<\/strong><strong>groups<\/strong>\u00a0<span style=\"color: #0000ff;\"><strong><em>increase<\/em><\/strong><\/span> the rate of electrophilic aromatic substitution, relative to hydrogen.<\/li>\n<li><strong>Deactivating groups<\/strong>\u00a0<span style=\"color: #ff0000;\"><strong><em>decrease<\/em><\/strong><\/span> the rate of electrophilic aromatic substitution, relative to hydrogen.<\/li>\n<\/ul>\n<p>If you look through the list of\u00a0<em>ortho- , para-\u00a0<\/em>directors, you might recognize that many of them are also activating groups.<\/p>\n<p>Likewise, the list of\u00a0<em>meta-<\/em> directors (nitro, CF<sub>3<\/sub>, cyano) is like a who&#8217;s who of\u00a0deactivating groups.<\/p>\n<p>If you&#8217;re a real nerd, you could even make a 2\u00a0\u00d7 2 matrix, like this:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15874\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-table-of-activating-deactivating-ortho-para-meta-directors-matrix.gif\" alt=\"table of activating deactivating ortho para meta directors matrix\" width=\"600\" height=\"508\" \/><\/p>\n<p>What do we notice?<\/p>\n<ul>\n<li>First: no activating groups are <em>meta<\/em> directors.<\/li>\n<li>Second: what&#8217;s up with the halogens?<\/li>\n<\/ul>\n<p>Yes indeed. What\u00a0<em>is<\/em> up with the halogens, and how is it that they can be deactivating (i.e. slow down the reaction rate) and\u00a0<em>yet<\/em> lead to\u00a0<em>ortho-, para-\u00a0<\/em>products?<\/p>\n<h2><a id=\"four\"><\/a>4. The Key To Understanding <em>ortho-, para-\u00a0<\/em>Directors and <em>meta-<\/em> Directors Is To Understand The Stability of The Carbocation Intermediate<\/h2>\n<p>There&#8217;s no quick\u00a0<em>and<\/em> thorough answer to these questions, and it&#8217;s worth its own separate article for that reason.<\/p>\n<p>However, the first place to start\u00a0is that it has to do with the stability of the <strong>carbocation intermediate<\/strong> in electrophilic aromatic substitution reactions. <em>[See this previous post on <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/11\/09\/electrophilic-aromatic-substitution-the-mechanism\/\">the mechanism of electrophilic aromatic substitution<\/a>].\u00a0<\/em> More specifically, how does each substituent affect the stability of that intermediate?<\/p>\n<p>It might be worth going back and revisiting some of the <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/03\/11\/3-factors-that-stabilize-carbocations\/\">factors that affect the stability (and instability) of carbocations<\/a>.<\/p>\n<p>In our next post, we&#8217;ll explain the reasons for\u00a0both\u00a0<em>ortho-, para-<\/em> and\u00a0<em>meta-<\/em> direction, and try to show why halogens fit in the former category but not the latter.<\/p>\n<p><strong>Next Post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/02\/02\/understanding-ortho-para-meta-directors\/\">Understanding Ortho, Meta, and Para Directors<\/a><\/strong><\/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\/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\/2017\/09\/26\/activating-and-deactivating-groups-in-electrophilic-aromatic-substitution\/\" class=\"\"><span>Activating and Deactivating Groups In Electrophilic Aromatic Substitution<\/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\/2011\/12\/15\/exploring-resonance-pi-donation\/\" class=\"\"><span>Exploring Resonance:  Pi-Donation<\/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 (MOC Membership)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/03\/11\/3-factors-that-stabilize-carbocations\/\" class=\"\"><span>3 Factors That Stabilize Carbocations<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/03\/21\/three-factors-that-destabilize-carbocations\/\" class=\"\"><span>Three Factors that Destabilize Carbocations<\/span><\/a><\/li><\/ul><\/div>\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\/2447-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\/2889-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\/2890-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\/2891-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\/2892-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\/2893-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\/2894-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\/2895-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\/2896-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\/2897-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\/2898-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>Two Important Reaction Patterns: Ortho- , Para- Directors and Meta- Directors It&#8217;s one thing to learn about electrophilic aromatic substitution reactions of benzene itself. But <\/p>\n","protected":false},"author":1,"featured_media":30114,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1297],"tags":[1298,1275,319,1285],"post_folder":[],"class_list":["post-11246","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-aromatic-reactions","tag-activating","tag-deactivating-group","tag-electrophilic-aromatic-substitution","tag-ortho-para-meta"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Ortho-, Para- and Meta- Directors in Electrophilic Aromatic Substitution<\/title>\n<meta name=\"description\" content=\"What are ortho, para directors? What are meta directors? Are all activating groups ortho, para directors? (hint: no) Are all deactivating groups meta? 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