{"id":3928,"date":"2012-01-10T12:00:14","date_gmt":"2012-01-10T18:00:14","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=3928"},"modified":"2024-12-05T15:46:31","modified_gmt":"2024-12-05T21:46:31","slug":"common-mistakes-how-not-to-draw-resonance-curved-arrows","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2012\/01\/10\/common-mistakes-how-not-to-draw-resonance-curved-arrows\/","title":{"rendered":"Drawing Resonance Structures: 3 Common Mistakes To Avoid"},"content":{"rendered":"<p><strong>How To Draw Resonance Structures: Avoiding Common Mistakes<\/strong><\/p>\n<p>No discussion of resonance structures would be complete without mention of <em>how to royally screw them up<\/em>.\u00a0This isn&#8217;t something to feel bad about, by the way: there isn&#8217;t a chemist alive who hasn&#8217;t made one of these mistakes at some point. Think of it as a rite of passage.\u00a0<strong>The trick is to make the mistakes while doing problems,\u00a0not\u00a0while doing an exam<\/strong>.<\/p>\n<p>There are at least three common categories of mistakes regarding resonance structures:<\/p>\n<ul>\n<li>Unbalanced equations<\/li>\n<li>Moving atoms around<\/li>\n<li>Incorrect drawing of resonance arrows<\/li>\n<\/ul>\n<p>Let&#8217;s deal them each in turn.<\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-38619\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/12\/0-Summary-of-three-important-mistakes-to-avoid-when-drawing-resonance-structures-dont-add-atoms-dont-break-single-bonds-and-dont-break-the-octet-rule.gif\" alt=\"Summary of three important mistakes to avoid when drawing resonance structures - don't add atoms don't break single bonds and don't break the octet rule\" width=\"640\" height=\"537\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Mistake #1: Unbalanced Resonance Equations<\/a><\/li>\n<li><a href=\"#two\">Mistake #2 :Moving Atoms Around<\/a><\/li>\n<li><a href=\"#three\">Mistake #3 : Incorrectly Drawing Curved Arrows<\/a><\/li>\n<li><a href=\"#four\">How To Avoid Making Mistakes Drawing Resonance Structures<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><a id=\"one\"><\/a>1. Common Resonance Structure Mistake #1 : Drawing Unbalanced Resonance Equations<\/h2>\n<p>Let&#8217;s first talk about\u00a0<strong>unbalanced <\/strong>resonance equations, where something (either an atom or electrons) has been added or subtracted. Remember that in drawing resonance forms we&#8217;re <strong>only allowed to move electrons<\/strong>, and nothing more. That means that the two resonance forms can neither differ in the number of their electrons nor can they differ in the number of atoms.<\/p>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14107\" title=\"1-unbalanced\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/1-common-mistakes-resonance-forms-drawing-unbalanced-resonance-forms-add-hydrogens-and-electrons.gif\" alt=\"common-mistakes-resonance-forms-drawing-unbalanced-resonance-forms-add-hydrogens-and-electrons\" width=\"625\" height=\"502\" \/><\/p>\n<h2><strong><a id=\"two\"><\/a>2. Common Resonance Mistake #2 :Moving Atoms Around<\/strong><\/h2>\n<p>A second category of common mistake is to move atoms around.\u00a0 Although the two structures shown below have the same number of atoms and electrons, they are not resonance forms because we have broken <strong>single<\/strong> bonds (as opposed to \u03c0 bonds) and thus moved the location of one or several <strong>atoms<\/strong>. The easiest way to screw this up is to move <strong>hydrogens<\/strong>.<\/p>\n<p>While these molecules are related, they are actually pairs of constitutional isomers, not resonance structures.<\/p>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14108\" title=\"2-moveatoms\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/2-common-mistakes-with-resonance-forms-moving-atoms-breaking-sigma-bonds.gif\" alt=\"common-mistakes-with-resonance-forms-moving-atoms-breaking-sigma-bonds\" width=\"630\" height=\"330\" \/><\/p>\n<p>One way to avoid making these types of mistakes is to try to interconvert the structures using <a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/02\/15\/curved-arrows-for-reactions\">curved arrows<\/a>.<\/p>\n<p>There are only <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/11\/30\/introduction-to-resonance-2-curved-arrows\/\">three legal arrow-pushing moves<\/a> for drawing resonance structures. Double check to make sure you aren&#8217;t breaking the rules.<\/p>\n<h2><strong><a id=\"three\"><\/a>3. Resonance Mistake #3 : Incorrectly Drawing Curved Arrows\u00a0<\/strong><\/h2>\n<p>The last &#8211; and by far the most common class of mistake in drawing resonance structures is to screw up the <strong>curved arrows<\/strong>. There is a seemingly infinite number of different ways to do this. They fall into a number of sub-categories.<\/p>\n<p><strong>Breaking The Octet Rule<\/strong><\/p>\n<p>First, there&#8217;s <strong>arrow-pushing moves that are wrong and cannot be redeemed.<\/strong> Examples A-D each depict different ways of breaking the octet rule. In A, B, and C the resonance form that would result from these arrows would have five bonds to carbon. Example D would have <strong>five<\/strong> bonds to nitrogen. <em>Inconceivable!\u00a0<\/em><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14109\" title=\"3-arrowpushing\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/3-arrow-pushing-mistakes-with-resonance-dont-break-octet-rule.gif\" alt=\"arrow-pushing-mistakes-with-resonance-dont-break-octet-rule\" width=\"630\" height=\"336\" \/><\/p>\n<p>Examples E and F\u00a0 are wrong for a different reason: remember that the curved arrow depicts the movement of a pair of electrons. In example E, the &#8220;tail&#8221; of the leftmost arrow is shown at a positive charge &#8211; a big no-no, since there isn&#8217;t a lone pair of electrons here. Likewise for F, where the positively charged nitrogen also lacks an electron pair.<\/p>\n<p><strong>Missing A Curved Arrow<\/strong><\/p>\n<p>Then there&#8217;s arrow pushing &#8220;moves&#8221; that are also illegal, <strong>but can\u00a0be made legal through drawing an additional arrow<\/strong>. See if you can draw an arrow to make it work (answers at the bottom (<a href=\"#noteone\">Note 1<\/a>).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14110\" title=\"4-makelegal\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/4-arrow-pushing-mistakes-resonance-how-to-fix-with-one-error-breaking-octet-rule.gif\" alt=\"arrow-pushing-mistakes-resonance-how-to-fix-with-one-error-breaking-octet-rule\" width=\"630\" height=\"231\" \/><\/p>\n<p><strong>Forgetting To Draw In Lone Pairs\u00a0<\/strong><\/p>\n<p>Then there&#8217;s the <strong>sloppy mistakes<\/strong>, where these arrow pushing forms are missing something important. I guess you could say this entire post is devoted to sloppy mistakes but these examples are particularly egregious because they are just one tiny little detail away from being correct.<\/p>\n<p>In the two cases below, there is neither a lone pair of electrons (or a formal negative charge) at the tail of one of the electron-pushing arrows, which make them incorrect. Neglecting to draw the formal charge of an atom is another common sloppy mistake (albeit not unique to resonance).<\/p>\n<p>Note that when I say sloppy I&#8217;m not making a moral judgement here. I&#8217;m just saying it makes for imprecise and ambiguous chemical structures, which are not useful.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14111\" title=\"5-missing\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/5-fix-resonance-form-arrow-pushing-by-drawing-in-source-of-electrons.gif\" alt=\"fix-resonance-form-arrow-pushing-by-drawing-in-source-of-electrons\" width=\"630\" height=\"270\" \/><\/p>\n<p>Finally, there are resonance structures which are not illegal, per se, but \u00a0won&#8217;t make a significant contribution to the resonance hybrid.<\/p>\n<p><strong>Insignificant Resonance Structures<\/strong><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14112\" title=\"6-insignif\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/6-resonance-quiz-why-are-these-resonance-forms-insignificant.gif\" alt=\"resonance-quiz-why-are-these-resonance-forms-insignificant\" width=\"630\" height=\"177\" \/><\/p>\n<p>In both examples we have very electronegative elements (oxygen and nitrogen) with less than a full octet.<\/p>\n<p>Recall that electronegativity is a rough measure of the ability of an atom to stabilize negative charge?<\/p>\n<p>Well, the\u00a0<em>converse<\/em>\u00a0is true &#8211; that is, the greater the electronegativity, the more positive charge will be <em>destabilized<\/em> on that atom (<span style=\"color: #993366;\"><em><strong>clarification:\u00a0<\/strong>by &#8220;positive charge&#8221; here I am specifically referring to having <strong>less than a full octet of electrons<\/strong> (like a carbocation),\u00a0not\u00a0the common situation where O or N with a full octet bears a formal charge of +1.<\/em><\/span>)<\/p>\n<h2><strong><a id=\"four\"><\/a>4. How To Avoid Making Mistakes Drawing Resonance Structures<\/strong><\/h2>\n<p>Avoiding all of these mistakes requires careful attention to detail, bordering on paranoia.<\/p>\n<p>The number of atoms and electrons on the left side of the resonance arrow should <strong>balance<\/strong> the number of atoms and electrons on the right side of the resonance arrow.<\/p>\n<p>Furthermore, the changes in bonding (and charge) \u00a0of the molecule on the left side of the arrow should be <strong>accurately mapped<\/strong>\u00a0by the appropriate curved arrow(s).<\/p>\n<p>If it sounds like I&#8217;m making a case for organic chemistry being a lot like accounting, you&#8217;re right! \u00a0In the final analysis,\u00a0<strong>organic chemistry equations are not unlike accounting transactions<\/strong>. The two sides need to balance.<\/p>\n<p><strong>Next Post: <\/strong><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/01\/17\/how-to-apply-electronegativity-and-resonance-to-understand-reactivity\/\">How To Apply Resonance and Electronegativity To Understand Reactivity<\/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\/2012\/01\/17\/how-to-apply-electronegativity-and-resonance-to-understand-reactivity\/\" class=\"\"><span>How to apply electronegativity and resonance to understand reactivity<\/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\/2012\/02\/15\/curved-arrows-for-reactions\/\" class=\"\"><span>Curved Arrows (for reactions)<\/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\/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\/2011\/12\/12\/evaluating-resonance-structures-2-applying-electronegativity\/\" class=\"\"><span>How To Find The Best Resonance Structure By Applying Electronegativity<\/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<p><strong><a id=\"noteone\"><\/a>Note 1. <\/strong>\u00a0Here&#8217;s the answers for the example above:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14113\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/7-answers-for-problems-resonance-form-adding-extra-curved-arrows.gif\" alt=\"answers-for-problems-resonance-form-adding-extra-curved-arrows\" width=\"630\" height=\"695\" \/><\/p>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>How To Draw Resonance Structures: Avoiding Common Mistakes No discussion of resonance structures would be complete without mention of how to royally screw them up.\u00a0This <\/p>\n","protected":false},"author":1,"featured_media":38619,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1406],"tags":[385,298,384,236,267],"post_folder":[],"class_list":["post-3928","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-bonding-structure-resonance","tag-accounting","tag-curved-arrows","tag-electrons","tag-mistakes","tag-resonance"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Drawing Resonance Structures: 3 Common Mistakes To Avoid<\/title>\n<meta name=\"description\" content=\"Here&#039;s a primer on how to avoid the most common mistakes in drawing resonance structures. 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