{"id":1624,"date":"2011-06-27T09:00:18","date_gmt":"2011-06-27T14:00:18","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=1624"},"modified":"2026-04-22T09:50:23","modified_gmt":"2026-04-22T14:50:23","slug":"hidden-hydrogens-hidden-lone-pairs-hidden-counterions","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2011\/06\/27\/hidden-hydrogens-hidden-lone-pairs-hidden-counterions\/","title":{"rendered":"Hidden Hydrogens, Hidden Lone Pairs, Hidden Counterions"},"content":{"rendered":"<p><strong>Hidden Hydrogens, Lone Pairs, and Counter-Ions<\/strong><\/p>\n<p>Time is precious. Drawing the full structures of chemical formulae out takes time.<\/p>\n<p>Shaving an extra 10-20 seconds here or there might not sound like a lot to you, but you might be surprised by what people will do to take 5 seconds of boredom off their journey. (<span style=\"color: #993366;\"><em>See article: <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2010\/09\/20\/the-power-of-laziness\/\">The Power of Laziness<\/a><\/em><\/span>)<\/p>\n<p>The point is, corners will get cut and shortcuts are inevitable. This post is about <strong>the shortcuts you have to know about when looking at chemical structures<\/strong>.<\/p>\n<p>There are 3 common types of shortcuts that organic chemists make when drawing structures. They will omit drawing the following:<\/p>\n<ul>\n<li>hydrogen atoms<\/li>\n<li>lone pairs<\/li>\n<li>counter-ions<\/li>\n<\/ul>\n<p>The key is learning to recognize the things that &#8220;you&#8217;re just supposed to know are there&#8221;.<\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-38631\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/12\/0-summary-hidden-explicit-hydrogens-lone-pairs-charges-make-sure-you-can-work-backwards-implicit-groups.gif\" alt=\"-summary-hidden explicit hydrogens lone pairs charges make sure you can work backwards implicit groups\" width=\"640\" height=\"646\" \/><\/a><\/p>\n<h2><strong><a id=\"one\"><\/a>1. Hidden hydrogens<\/strong><\/h2>\n<p>Line drawings are the chemists&#8217; method of choice for depicting structures. And it&#8217;s not hard to see why: they&#8217;re a snap to draw. Why? Because we omit drawing in all the pesky little hydrogens!<\/p>\n<p>The key thing in recognizing hidden hydrogens is that wherever you see <strong>less<\/strong> than <strong>4 bonds<\/strong> to carbon, that carbon is going to have hydrogens attached such that there&#8217;s a<strong> full octet<\/strong>. Here are some examples.<\/p>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14199\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-implicit-hydrogen-examples-with-full-structure-revealed.gif\" alt=\"implicit-hydrogen-examples-with-full-structure-revealed\" width=\"595\" height=\"381\" \/><\/p>\n<h2><strong><a id=\"two\"><\/a>2. Hidden lone pairs<\/strong><\/h2>\n<p>Lone pairs are often not drawn on structures either. Again, this is a time-saving measure, but also they tend to get in the way and clutter up the structure. Like hydrogens, you&#8217;re &#8220;just supposed to know that they&#8217;re there&#8221;.<\/p>\n<p>How do you know how many to draw? If you understand formal charge, this should be a snap.<\/p>\n<p>(<span style=\"color: #993366;\"><em>For more on formal charges, see: <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2010\/09\/24\/how-to-calculate-formal-charge\/\">How To Calcluate Formal Charge<\/a><\/em><\/span>)<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-40873\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/06\/2-implicit-lone-pairs-examples-with-lone-pairs-revealed.gif\" alt=\"implicit lone pairs examples with lone pairs revealed\" width=\"640\" height=\"990\" \/><\/a><\/p>\n<p>The atom that causes the most confusion on this point is probably carbon when it is drawn with a negative charge:<strong> the negative charge implies the existence of a lone pair<\/strong>.<\/p>\n<p>This also comes up in reactions. Using the curved arrow notation, you&#8217;ll often see the tail of an arrow coming from a negative charge on a given atom. You&#8217;re just supposed to know that the negative charge represents a pair of electrons on the atom.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14201\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-implicit-lone-pair-example-negative-charge-on-oxygen-implies-presence-of-lone-pair.gif\" alt=\"implicit-lone-pair-example-negative-charge-on-oxygen-implies-presence-of-lone-pair\" width=\"595\" height=\"197\" \/><\/p>\n<p>Finally, if you see a <strong>positive charge<\/strong> on carbon, you&#8217;re supposed to know that not only are there <strong>zero<\/strong> lone pairs on the carbon, there are only 3 bonds.<\/p>\n<h2><strong><a id=\"three\"><\/a>3. Hidden Counter-ions\u00a0<\/strong><\/h2>\n<p>The subject of counterions also causes a lot of confusion. Students coming out of gen chem where they have had to balance these massive redox equations often get confused when they notice their instructor (or the textbook) not balancing charges anymore. It&#8217;s a signal that &#8220;suddenly the charges aren&#8217;t that important&#8221;, or even worse, they aren&#8217;t there.<\/p>\n<p>The charge IS there, <strong>it just hasn&#8217;t been drawn in<\/strong>.<\/p>\n<p>Charge is <strong>always<\/strong> conserved, and balanced: the presence of a charge <strong>implies<\/strong> the existence of an equal and opposite charge somewhere else. Always.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14202\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-implied-or-hidden-counter-ions-such-as-in-negatively-charged-species-with-postiively-charged-metal-salts.gif\" alt=\"implied-or-hidden-counter-ions-such-as-in-negatively-charged-species-with-postiively-charged-metal-salts\" width=\"595\" height=\"953\" \/><\/p>\n<p>The reason why the balancing ions are often left off, I think, is not due to simple laziness but also for a desire to avoid confusion by focusing on specifics.\u00a0 It&#8217;s a bit of a Catch-22.<\/p>\n<ul>\n<li>If the counterion is <strong>omitted<\/strong>, one risks <strong>confusing<\/strong> the students by implying that the charges are <strong>unbalanced<\/strong>.<\/li>\n<li>However, if one puts in a <strong>specific<\/strong> counterion such as Cl(-) , then one will have to eventually <strong>explain<\/strong> that Cl(-) is <strong>not crucial<\/strong> to the reaction and any number of other counterions would work just as well.<\/li>\n<\/ul>\n<p>My compromise is to use X(-) or M(+) for this purpose.\u00a0\u00a0The exact counterion for a given reaction will depend on how the ion is made in the first place.<\/p>\n<h2><strong>4. Hidden Charges<\/strong><\/h2>\n<p>A related issue is not hidden counterions but <strong>hidden charges<\/strong>. Specifically, ionic compounds.<\/p>\n<p>Again, it&#8217;s easier to just <strong>omit<\/strong> drawing in charges rather than drawing them in.<\/p>\n<p>A classic example is <strong>NaOH<\/strong>. From general chemistry, it&#8217;s well understood that NaOH is an <strong>ionic<\/strong> compound and is better represented as Na(+)OH(-). However oftentimes the charges will be omitted.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14203\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-implicit-charges-hidden-charges-naoh-and-naoet-dont-show-charges.gif\" alt=\"implicit-charges-hidden-charges-naoh-and-naoet-dont-show-charges\" width=\"595\" height=\"267\" \/><\/p>\n<p>Hopefully now you&#8217;ll have a better idea of the things that you&#8217;re &#8220;just supposed to know are there&#8221;.<\/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\/11\/10\/dont-be-futyl-learn-the-butyls\/\" class=\"\"><span>Don\u2019t Be Futyl, Learn The Butyls<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/06\/16\/1-2-3-4\/\" class=\"\"><span>Primary, Secondary, Tertiary, Quaternary In Organic Chemistry<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/07\/09\/branching-melting-boiling-points\/\" class=\"\"><span>Branching, and Its Affect On Melting and Boiling Points<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/10\/15\/the-many-many-ways-to-draw-butane\/\" class=\"\"><span>The Many, Many Ways of Drawing Butane<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/03\/12\/common-mistakes-drawing-tetrahedral-carbons\/\" class=\"\"><span>Common Mistakes: Drawing Tetrahedral Carbons<\/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\/2010\/10\/06\/functional-groups-organic-chemistry\/\" class=\"\"><span>Meet the (Most Important) Functional Groups<\/span><\/a><\/li><\/ul><\/div>\n<hr 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class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3477-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3478-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3479-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Hidden Hydrogens, Lone Pairs, and Counter-Ions Time is precious. Drawing the full structures of chemical formulae out takes time. Shaving an extra 10-20 seconds here <\/p>\n","protected":false},"author":1,"featured_media":38631,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1408],"tags":[566,196,408,567,229,242,276],"post_folder":[],"class_list":["post-1624","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alkanes-nomenclature","tag-blind-spots","tag-conventions","tag-hidden-hydrogens","tag-hidden-lone-pairs","tag-line-drawings","tag-nomenclature","tag-structure-drawings"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Hidden Hydrogens, Hidden Lone Pairs, Hidden Counterions &#8211; Master Organic Chemistry<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.masterorganicchemistry.com\/2011\/06\/27\/hidden-hydrogens-hidden-lone-pairs-hidden-counterions\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Hidden Hydrogens, Hidden Lone Pairs, Hidden Counterions &#8211; Master Organic Chemistry\" \/>\n<meta property=\"og:description\" content=\"Hidden Hydrogens, Lone Pairs, and Counter-Ions Time is precious. 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