{"id":3622,"date":"2011-12-14T12:00:35","date_gmt":"2011-12-14T12:00:35","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=3622"},"modified":"2026-01-22T09:15:39","modified_gmt":"2026-01-22T15:15:39","slug":"resonance-structures-full-octets-carbocations","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2011\/12\/14\/resonance-structures-full-octets-carbocations\/","title":{"rendered":"Resonance Structures Should Have Full Octets (If Possible!)"},"content":{"rendered":"<p><strong>Resonance Structures With Positive Charge: Four Key Principles<\/strong><\/p>\n<p>The most important resonance form is generally the one where<a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/08\/evaluating-resonance-forms-1-the-rule-of-least-charges\/\" target=\"_blank\" rel=\"noopener noreferrer\"> the charges are minimized<\/a>.<\/p>\n<p>However, sometimes you can&#8217;t get around it: you have to put a charge <strong>somewhere<\/strong>.<\/p>\n<p>Two important rules in this article.<\/p>\n<ul>\n<li>First, if you must have a resonance form with a positive charge, a resonance form where\u00a0<strong>all atoms have full octets\u00a0<\/strong>will be preferred.<\/li>\n<li>Second, if having a carbocation is unavoidable, then the resonance form where the carbocation is on the <strong>most substituted carbon\u00a0<\/strong>(tertiary &gt; secondary &gt; primary) will make the\u00a0<strong>greatest contribution\u00a0<\/strong>to the hybrid.<\/li>\n<li>This is because carbocation stability increases as the number of attached carbons increase (<span style=\"color: #993366;\"><em>See Article: <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/03\/11\/3-factors-that-stabilize-carbocations\/\">Three Factors That Stabilize Carbocations<\/a><\/em><\/span>)<\/li>\n<\/ul>\n<p>At the bottom of this article are several\u00a0<strong>quizzes<\/strong> that will test you on these concepts.<\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-38644\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/12\/0-summary-determining-best-resonance-form-with-positive-charge-choose-form-with-full-octets-stabilize-carbocations.gif\" alt=\"summary-determining best resonance form with positive charge choose form with full octets stabilize carbocations\" width=\"640\" height=\"743\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Electron-Deficient Atoms Are Stabilized By Electron-Rich Neighbors<\/a><\/li>\n<li><a href=\"#two\">Positive Formal Charges On Oxygen Or Nitrogen Are OK So Long As It Has A Full Octet<\/a><\/li>\n<li><a href=\"#three\">When Placing Positive Charges On \u00a0Carbon, The Resonance Form Where The Positive Charge Is On The Most Substituted Carbon Will Be The Most Important<\/a><\/li>\n<li><a href=\"#four\">Carbocations Are Destabilized By Adjacent Electron Withdrawing Groups That Lack Lone Pairs (Such As CF3, NR3+, And C=O)<\/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. Electron-Deficient Atoms Are Stabilized By Electron-Rich Neighbors<\/strong><\/h2>\n<p>There are really one main principle to think about when deciding which site will stabilize positive charge the best. Recall the one sentence summary of chemistry: opposite charges attract, like charges repel.<\/p>\n<ul>\n<li><em>Electron-poor atoms are <strong>stabilized<\/strong> by adjacent electron-rich atoms. <\/em><\/li>\n<li><em>Electron poor atoms are <\/em><strong><em>destabilized<\/em><\/strong><em> by adjacent electron-poor atoms.\u00a0<\/em><\/li>\n<\/ul>\n<p>To be more specific, there are three main ways this plays out when evaluating resonance structures.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-42688\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/11\/1-evaluating-resonance-forms-with-positive-charges-principles-give-atom-full-octet-when-possible-rev.gif\" alt=\"-evaluating resonance forms with positive charges principles give atom full octet when possible-rev\" width=\"640\" height=\"255\" \/><\/a><\/p>\n<p>It&#8217;s probably this first principle which causes the most confusion of all. Let&#8217;s look at the &#8220;best&#8221; and &#8220;second-best&#8221; resonance forms for these positively charged species.<\/p>\n<p>Notice how in each one, the second-best resonance form has a carbocation &#8211; that is, a <strong>carbon with six valence electrons.<\/strong><\/p>\n<p>The best resonance form has a new <strong>\u03c0<\/strong> bond that has been formed through the donation of a pair of electrons on the adjacent atom (O, N, Cl, F). In the process we put a <strong>positive<\/strong> charge on that atom.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-42689\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/11\/2-determine-importance-of-resonance-forms-promote-full-octets-when-possible-rev.gif\" alt=\"determine importance of resonance forms promote full octets when possible-rev\" width=\"641\" height=\"332\" \/><\/a><\/p>\n<h2><a id=\"two\"><\/a>2. Positive Formal Charges On Oxygen Or Nitrogen Are OK So Long As It Has A Full Octet<\/h2>\n<p>Why is this weird? Because up to this point, you&#8217;re probably used to thinking of atoms like F, \u00a0O, Cl, and N as the &#8220;electron Scrooges&#8221; of the periodic table. Due to their high electronegativity they take electrons away from whatever they&#8217;re attached to.<\/p>\n<p>Here&#8217;s an important new concept: <strong>When atoms with a lone pair are adjacent to an atom with an empty orbital, formation of a <strong>\u03c0\u00a0<\/strong>bond will be favored. <\/strong>Remember that <em>formation of a chemical bond is an energy-lowering event.<\/em> The &#8220;loss&#8221; of a full lone pair on the donating atom is more than compensated for by the energy released through formation of a new <strong>\u03c0<\/strong> bond to the empty orbital.<\/p>\n<p>We call this <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/15\/exploring-resonance-pi-donation\/\"><strong><strong>\u03c0<\/strong><\/strong> donation<\/a>. It&#8217;s such an important concept there will be much more to say about it in a subsequent post, but if you want to anthropomorphize matters here, you can compare F, O, N and Cl to \u00a0famous Scrooges such as John D. Rockefeller, Andrew Carnegie, and even Bill Gates: \u00a0while they may have been thought of as greedy, they also have a philanthropic side.<\/p>\n<p>Just one thing to note: although it might look &#8220;bad&#8221; to put a positive charge on electronegative atoms such as O, N, Cl, and F,\u00a0 this is fine in these cases because if you look closely there is a full octet of electrons on each of these atoms. Recall that the &#8220;positive charge&#8221; we draw is actually <strong>formal charge<\/strong>, and remember that <strong><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/11\/15\/how_to_use_electronegativity\/\" target=\"_blank\" rel=\"noopener noreferrer\">formal charge does not always reflect electron density<\/a>.\u00a0<\/strong> So in these cases these atoms are not actually electron-deficient.<\/p>\n<p>However it&#8217;s important to distinguish between these types of positively charged atoms, and those in the diagram below which lack a full octet. <strong><em>It is extremely energetically unfavorable for atoms like F, O, and N to have less than a full octet of electrons.\u00a0<\/em> <\/strong>Avoid!<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42690\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/11\/3-good-versus-bad-positive-charges-on-oxygen-nitrogen-and-chlorine-as-long-as-they-have-full-octet-rev.gif\" alt=\"good versus bad positive charges on oxygen nitrogen and chlorine as long as they have full octet-rev\" width=\"640\" height=\"509\" \/><\/a><\/p>\n<h2><strong><a id=\"three\"><\/a>3. When Placing Positive Charges On \u00a0Carbon, The Resonance Form Where The Positive Charge Is On The Most Substituted Carbon Will Be The Most Important<\/strong><\/h2>\n<p>Here comes the second most important principle when it comes to stabilizing positive charge: if possible, it is best to place the positive charge on the most substituted carbon atom. As I often say to my students, &#8220;if you&#8217;re poor, it helps to have rich neighbors&#8221;. The stability of carbocations increases with the number of attached alkyl groups. It might be useful to review the <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/03\/11\/3-factors-that-stabilize-carbocations\/\" target=\"_blank\" rel=\"noopener noreferrer\">3 factors that stabilize carbocations.<\/a><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42691\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/11\/4-carbocations-increase-in-stability-as-number-of-attached-carbons-increases-rev.gif\" alt=\"carbocations increase in stability as number of attached carbons increases-rev\" width=\"639\" height=\"372\" \/><\/a><\/p>\n<h2><a id=\"four\"><\/a>4. Carbocations Are Destabilized By Adjacent Electron Withdrawing Groups That Lack Lone Pairs (Such As CF<sub>3<\/sub>, NR<sub>3<\/sub>+, And C=O)<\/h2>\n<p>The last factor to keep in mind is essentially the <strong>inverse<\/strong> of what we just discussed. Carbocations are <em>destabilized<\/em> when adjacent to electron-withdrawing groups. Now it&#8217;s important to add the caveat &#8211; <em>electron withdrawing groups that cannot donate a lone pair<\/em>.<\/p>\n<p>So we can put groups such as CF<sub>3<\/sub>, NR<sub>3<\/sub>,(+) COOR, COOH, SO<sub>3<\/sub>H, NO<sub>2<\/sub>, and others in this category. Let&#8217;s have a look.<\/p>\n<p>Note that in each case the carbocation is attached to a group which is removing electron density from it *without* being able to donate a lone pair of electrons.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42692\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/11\/5-carbocations-are-destabilized-by-adjacent-groups-that-remove-electron-density-rev.gif\" alt=\"carbocations are destabilized by adjacent groups that remove electron density-rev\" width=\"640\" height=\"875\" \/><\/a><\/p>\n<p>So hopefully that (mostly) covers an introduction to evaluating the stability of different resonance forms. In the next few posts, we&#8217;ll start to look at how to apply resonance to find the reactive sites on a molecule.<\/p>\n<p><strong>Next Post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/15\/exploring-resonance-pi-donation\/\">Applying Resonance (1): Pi-donation<\/a><\/strong><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/15\/exploring-resonance-pi-donation\/\">\u00a0<\/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\/2011\/12\/15\/exploring-resonance-pi-donation\/\" class=\"\"><span>Exploring Resonance:  Pi-Donation<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/08\/evaluating-resonance-forms-1-the-rule-of-least-charges\/\" class=\"\"><span>Evaluating Resonance Forms (1) \u2013 The Rule of Least Charges<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/11\/30\/introduction-to-resonance-2-curved-arrows\/\" class=\"\"><span>How To Use Curved Arrows To Interchange Resonance Forms<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/01\/10\/common-mistakes-how-not-to-draw-resonance-curved-arrows\/\" class=\"\"><span>Drawing Resonance Structures: 3 Common Mistakes To Avoid<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/22\/in-summary-resonance\/\" class=\"\"><span>In Summary: Evaluating Resonance Structures<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/01\/24\/conjugation-and-resonance\/\" class=\"\"><span>Conjugation And Resonance In Organic Chemistry<\/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\/organic-chemistry-practice-problems\/resonance-structures-practice\/\" class=\"\"><span>Resonance Structures Practice (MOC Membership)<\/span><\/a><\/li><\/ul><\/div>\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\/3663-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\/0008-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\/3676-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>Resonance Structures With Positive Charge: Four Key Principles The most important resonance form is generally the one where the charges are minimized. However, sometimes you <\/p>\n","protected":false},"author":1,"featured_media":38644,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1406],"tags":[173,397,334,199,379,388,267,396],"post_folder":[],"class_list":["post-3622","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-bonding-structure-resonance","tag-arrow-pushing","tag-carbocations","tag-electron-density","tag-electronegativity","tag-opposite-charges-attract","tag-positive-charge","tag-resonance","tag-stabilization-of-charge"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Resonance Structures Should Have Full Octets (If Possible!)<\/title>\n<meta name=\"description\" content=\"When a resonance structure has a positive charge, how do you decide where the &quot;best&quot; place to put it is? 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