{"id":3568,"date":"2011-12-12T12:00:09","date_gmt":"2011-12-12T12:00:09","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=3568"},"modified":"2026-01-16T14:18:35","modified_gmt":"2026-01-16T20:18:35","slug":"evaluating-resonance-structures-2-applying-electronegativity","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2011\/12\/12\/evaluating-resonance-structures-2-applying-electronegativity\/","title":{"rendered":"How To Find The Best Resonance Structure By Applying Electronegativity"},"content":{"rendered":"<p><strong>Finding The Best (And Second-Best) Resonance Structures By Applying Electronegativity<\/strong><\/p>\n<ul>\n<li>If any atom has to have less than a full octet, let it be on\u00a0<strong>carbon<\/strong>. Never have less than a full octet on oxygen or nitrogen, as these highly electronegative elements are highly stable without a full octet.<\/li>\n<li>Resonance forms with less than a full octet on oxygen or nitrogen can be considered to be\u00a0<strong>insignificant<\/strong>.<\/li>\n<li>When using curved arrows to interconvert resonance structures, always break them such that the <strong>more electronegative element<\/strong> gets the <strong>electron pair.<\/strong><\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-38637\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/12\/0-summary-drawing-resonance-structures-applying-electronegativity-always-break-pi-bonds-to-put-electrons-on-most-electronegative-atom.gif\" alt=\"summary-drawing resonance structures applying electronegativity always break pi bonds to put electrons on most electronegative atom\" width=\"640\" height=\"530\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Always Break A Pi Bond So As To Put The Electrons On The More Electronegative Atom<\/a><\/li>\n<li><a href=\"#two\">Evaluating The Resonance Structures Of Acetone (Propanone)<\/a><\/li>\n<li><a href=\"#three\">Evaluating The Resonance Structures Of An Imine<\/a><\/li>\n<li><a href=\"#four\">Evaluating The Resonance Structures Of The Acetate Ion<\/a><\/li>\n<li><a href=\"#five\">Apply The Rule Of Electronegativity To Determine The &#8220;Second-Best&#8221; Resonance Structures For These Molecules<\/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. Always Break A Pi Bond So As To Put The Electrons On The More Electronegative Atom<\/strong><\/h2>\n<p>The last time I talked about evaluating resonance structures the molecules were, to be honest &#8211; pretty simple. Evaluating the resonance structures of ethene, the allyl carbocation, and the allyl carbanion are a pretty far cry from some of the more complicated structures you&#8217;ll see in a typical course.<\/p>\n<p>So today let&#8217;s get started with how to evaluate non-equivalent resonance structures from pi bonds.<\/p>\n<p>So today I thought I&#8217;d start to talk about the (much more common) situation when you have a \u03c0 bond between two dissimilar atoms. How do you evaluate the resonance forms in these cases?<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-42780\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/1-evaluate-the-resonance-forms-of-these-molecules-acetone-co2-dimethyl-sulfoxide-hcn-ylide.gif\" alt=\"evaluate the resonance forms of these molecules acetone co2 dimethyl sulfoxide hcn ylide\" width=\"640\" height=\"159\" \/><\/a><\/p>\n<p>We&#8217;re going to have to go back to using our old friendly measuring stick, electronegativity for this task. Here&#8217;s the bottom line lesson for the resonance structures we&#8217;ll evaluate today.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-42781\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/2-second-rule-for-drawing-resonance-structures-always-break-pi-bond-to-put-electrons-on-the-more-electronegative-atom.gif\" alt=\"second rule for drawing resonance structures always break pi bond to put electrons on the more electronegative atom\" width=\"640\" height=\"353\" \/><\/a><\/p>\n<p>Hopefully this makes some sense! Charged resonance forms are less stable than neutral resonance forms. So if we absolutely must form a charged resonance form, it makes sense to put the negative charge on the atom best able to stabilize it. How do we know which atoms stabilize negative charge the best? Well, a pKa table will give you a really good idea. But beyond that, if you look at the five key factors that influence acidity, one of the most important factors is the electronegativity of an atom.\u00a0After all, electronegativity is ultimately a measure of<strong> to what extent an atom is able to stabilize negative charge<\/strong>.<\/p>\n<h2><a id=\"two\"><\/a>2. What Are The Best Resonance Structures Of Acetone (Propanone)?<\/h2>\n<p>So hopefully it should come as no surprise as we walk through these three examples that the second-best resonance forms are the ones where negative charge ends up on the more electronegative atom.<\/p>\n<p>Let&#8217;s start by looking at a simple carbonyl compound, acetone (propanone).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42782\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/3-carbonyl-compound-acetone-best-second-best-and-worst-resonance-forms-best-has-fewest-charges.gif\" alt=\"carbonyl compound acetone best second best and worst resonance forms best has fewest charges\" width=\"640\" height=\"560\" \/><\/a><\/p>\n<p>If we look at the possible curved-arrow &#8220;moves&#8221; for drawing the resonance forms of this molecule, there&#8217;s <strong>two<\/strong> possibilities.<\/p>\n<p>In the first possibility, we draw an arrow from the \u03c0\u00a0bond to the oxygen atom, putting a <strong>negative<\/strong> charge on the <strong>oxygen<\/strong> and leaving behind a <strong>positive<\/strong> charge on the <strong>carbon<\/strong>.<\/p>\n<p>In the second, we&#8217;re making the carbon negative and leaving behind a positive charge on the oxygen. Not only is there a positive charge on the oxygen, it has <strong>less<\/strong> than a<strong> full octet<\/strong>. <em>This is an extremely <span style=\"color: #ff0000;\">unstable<\/span> situation.<\/em><\/p>\n<p>So hopefully it&#8217;s clear that:<\/p>\n<ul>\n<li>the <strong>best<\/strong> resonance form is the <strong>neutral <\/strong>form with full octets<\/li>\n<li>the <strong>second-best <\/strong>resonance form is the one with a <strong>negative charge<\/strong> on <strong>oxygen <\/strong>(and less than a full octet on carbon), and<\/li>\n<li>the resonance form where there is a negative charge on carbon and less than a full octet on\u00a0<strong>oxygen<\/strong> is <strong>insignificant<\/strong>.<\/li>\n<\/ul>\n<p>Experiment bears this out. Calculations of the charge density on acetone reveal that the carbon is electropositive and the oxygen is electronegative, as per what we&#8217;d expect from electronegativity differences. So the molecule can be thought of as a <strong>hybrid<\/strong> of the <strong>best<\/strong> and <strong>second-best<\/strong> resonance forms.<\/p>\n<h2><a id=\"three\"><\/a>3. What Are The Best Resonance Structures Of This Imine?<\/h2>\n<p>Likewise, the resonance forms for the <strong>imine<\/strong> below similar behavior.<\/p>\n<p>As expected, calculations of electron density for this imine show that there is considerable <strong>positive<\/strong> charge density on the <strong>carbon<\/strong> and a high density of <strong>negative<\/strong> charge on the <strong>nitrogen<\/strong>. As you&#8217;d expect, the resonance form where there&#8217;s negative charge on carbon gets very little weight.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42783\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/4-best-resonance-forms-for-imine-is-neutral-second-best-has-positive-charge-on-carbon-and-negative-charge-on-nitrogen.gif\" alt=\"best resonance forms for imine is neutral second best has positive charge on carbon and negative charge on nitrogen\" width=\"640\" height=\"573\" \/><\/a><\/p>\n<h2><a id=\"four\"><\/a>4. What Are The Best Resonance Structures Of The Acetate Ion?<\/h2>\n<p>Finally we come to the acetate ion, which we discussed previously. Again, the second-best resonance form is that where there&#8217;s a positive charge on the carbon (and the worst is the one where it bears a negative charge).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42784\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/11\/5-resonance-forms-for-acetate-ion-best-are-negative-on-oxygen-second-best-has-three-charges.gif\" alt=\"resonance forms for acetate ion best are negative on oxygen second best has three charges\" width=\"640\" height=\"586\" \/><\/a><\/p>\n<h2><a id=\"five\"><\/a>5. Apply The Rule Of Electronegativity To Determine The &#8220;Second-Best&#8221; Resonance Structures For These Molecules<\/h2>\n<p>With these examples in mind, can you apply the rule to determine the &#8220;second-best&#8221; resonance forms for each of these molecules?<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-42785\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/11\/6-determine-second-best-resonance-forms-for-each-of-these-molecules-co2-dmso-hcn-h3po4.gif\" alt=\"determine second best resonance forms for each of these molecules co2 dmso hcn h3po4\" width=\"640\" height=\"289\" \/><\/a><\/p>\n<p class=\"p1\"><span class=\"s1\">To see the answer, <a href=\"\" class=\"custom-tooltip\" data-image=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2011\/12\/Screen-Shot-2014-01-05-at-12.35.15-PM.png\" data-link=\"\" data-title=\"\" data-text=\"\">hover here<\/a> or click on this <a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2011\/12\/Screen-Shot-2014-01-05-at-12.35.15-PM.png\">link<\/a>.\u00a0<\/span><\/p>\n<p>Next time I&#8217;ll go into a few more details on evaluating resonance forms based on lessons we learn from acidity and basicity.<\/p>\n<p><strong>Next Post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/evaluating-resonance-forms-3-where-to-put-the-negative-charge\/\">Evaluating Resonance Forms (3) &#8211; Where to Put Negative Charges<\/a><\/strong><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/13\/evaluating-resonance-forms-3-where-to-put-the-negative-charge\/\">\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\/13\/evaluating-resonance-forms-3-where-to-put-the-negative-charge\/\" class=\"\"><span>Evaluating Resonance Structures With Negative 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\/2020\/10\/02\/organic-chemistry-gifs-resonance-forms\/\" class=\"\"><span>Organic Chemistry GIFS \u2013 Resonance Forms<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/14\/evaluating-resonance-forms-4-positive-charges\/\" class=\"\"><span>Evaluating Resonance Structures With Positive Charge<\/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\/06\/07\/valence-electrons\/\" class=\"\"><span>Valence Electrons of the First Row Elements<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/09\/24\/how-to-calculate-formal-charge\/\" class=\"\"><span>A Key Skill: How to Calculate Formal Charge<\/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\/0009-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\/2267-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\/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","protected":false},"excerpt":{"rendered":"<p>Finding The Best (And Second-Best) Resonance Structures By Applying Electronegativity If any atom has to have less than a full octet, let it be on\u00a0carbon. <\/p>\n","protected":false},"author":1,"featured_media":38637,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1406],"tags":[199,401,388,267,400],"post_folder":[],"class_list":["post-3568","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-bonding-structure-resonance","tag-electronegativity","tag-fewest-charges","tag-positive-charge","tag-resonance","tag-stabilizing-negative-charge"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>How To Find The Best Resonance Structure By Applying Electronegativity<\/title>\n<meta name=\"description\" content=\"Finding the best and second-best resonance structures in molecules with C=O and C=N bonds by applying electronegativities - break the pi bond the right way!\" \/>\n<meta name=\"robots\" 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