{"id":11195,"date":"2018-01-16T07:00:41","date_gmt":"2018-01-16T13:00:41","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=11195"},"modified":"2026-04-17T21:14:33","modified_gmt":"2026-04-18T02:14:33","slug":"a-hybridization-shortcut","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2018\/01\/16\/a-hybridization-shortcut\/","title":{"rendered":"How To Determine Hybridization: A Shortcut"},"content":{"rendered":"<p><strong>A Shortcut For Determining The Hybridization Of An Atom In A Molecule<\/strong><\/p>\n<p>Here&#8217;s a shortcut for how to determine the hybridization of an atom in a molecule <strong>that will work in at least 95% of the cases you see in Org 1.\u00a0<\/strong><\/p>\n<p>For a given atom:<\/p>\n<ul>\n<li>Count the number of <strong>atoms<\/strong> connected to it <em><strong>(atoms &#8211; <\/strong>not bonds!)<\/em><\/li>\n<li>Count the number of <strong>lone pairs<\/strong> attached to it.<\/li>\n<li><strong>Add<\/strong> these two numbers together.<\/li>\n<\/ul>\n<ul>\n<li>If it&#8217;s <strong>4<\/strong>, your atom is <strong>sp<sup>3<\/sup>.<\/strong><\/li>\n<li>If it&#8217;s <strong>3<\/strong>, your atom is<strong> sp<sup>2<\/sup>.<\/strong><\/li>\n<li><span class=\"Apple-style-span\">If it&#8217;s <strong>2<\/strong>, your atom is <strong>sp.\u00a0<\/strong><\/span><\/li>\n<\/ul>\n<p>(If it&#8217;s 1, it&#8217;s probably hydrogen!)<\/p>\n<p>The main exception is atoms with lone pairs that are <strong>adjacent<\/strong> to pi bonds, which we&#8217;ll discuss in detail below.<\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-26357\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2018\/01\/0-tips-for-determining-hybridization-of-molecules.gif\" alt=\"-tips for determining hybridization of molecules\" width=\"640\" height=\"521\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Some Simple Worked Examples Of The Hybridization Shortcut<\/a><\/li>\n<li><a href=\"#two\">How To Determine Hybridization Of An Atom: Two Exercises<\/a><\/li>\n<li><a href=\"#three\">Are There Any Exceptions?<\/a><\/li>\n<li><a href=\"#four\">Exception #1: Lone Pairs Adjacent To Pi-bonds<\/a><\/li>\n<li><a href=\"#five\">Lone Pairs In P-Orbitals (Versus Hybrid Orbitals) Have Better Orbital Overlap With Adjacent Pi Systems<\/a><\/li>\n<li><a href=\"#six\">Exception #2. Geometric Constraints<\/a><\/li>\n<li><a href=\"#seven\">&#8220;Geometry Determines Hybridization, Not The Other Way Around&#8221;<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quiz\">Quiz Yourself!<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><a id=\"one\"><\/a>1. Some Simple Worked Examples Of The Hybridization Shortcut<\/h2>\n<p><strong>sp<sup>3<\/sup> hybridization<\/strong>: sum of attached <strong>atoms<\/strong> + <strong>lone pairs<\/strong> = <strong>4<\/strong><\/p>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14001\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/1-shortcut-for-calculating-hybridization-of-atoms-sp3-add-attached-atoms-plus-lone-pairs-three-examples.gif\" alt=\"shortcut-for-calculating-hybridization-of-atoms-sp3-add-attached-atoms-plus-lone-pairs-three-examples\" width=\"485\" height=\"184\" \/><\/p>\n<p><strong>sp<sup>2<\/sup> hybridization<\/strong>: sum of attached <strong>atoms<\/strong> +<strong> lone pairs<\/strong> = <strong>3<\/strong><\/p>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14002\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/2-three-hybridization-examples-calculation-sp2-carbonyl-alkene-imine.gif\" alt=\"three-hybridization-examples-calculation-sp2-carbonyl-alkene-imine\" width=\"480\" height=\"158\" \/><\/p>\n<p><strong>sp hybridization<\/strong>: sum of attached <strong>atoms<\/strong> + <strong>lone pairs<\/strong> = <strong>2<\/strong><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14003\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/3-3-hybridization-examples-sp-add-attached-atoms-plus-lone-pair-alkyne-nitrile-co.gif\" alt=\"hybridization-examples-sp-add-attached-atoms-plus-lone-pair-alkyne-nitrile-co\" width=\"475\" height=\"145\" \/><\/p>\n<p>Where it can start to get slightly tricky is in dealing with line diagrams <strong>containing implicit (&#8220;hidden&#8221;) hydrogens and lone pairs.<\/strong><\/p>\n<p>Chemists like time-saving shortcuts just as much as anybody else, and learning to quickly interpret line diagrams is as fundamental to organic chemistry as learning the alphabet is to written English.<\/p>\n<p>Remember:<\/p>\n<ul>\n<li>Just because lone pairs aren&#8217;t drawn in on oxygen, nitrogen, and fluorine <strong>doesn&#8217;t<\/strong> mean they&#8217;re not there.<\/li>\n<li><strong>Assume a full octet<\/strong> for C, N, O, and F with the following\u00a0<strong>one<\/strong> exception: a positive charge on carbon indicates that there are only <strong>six<\/strong> electrons around it. [<strong>Nitrogen<\/strong> and <strong>oxygen<\/strong> bearing a formal charge of +1 still have full octets].<\/li>\n<\/ul>\n<p><span style=\"color: #993366;\">[<em>Advanced: <a style=\"color: #993366;\" href=\"#noteone\">Note 1<\/a> covers how to determine the hybridization of atoms in some weird cases like free radicals, carbenes and nitrenes ]<\/em><\/span><\/p>\n<h2><strong><a id=\"two\"><\/a>2. How To Determine Hybridization Of An Atom: Two Exercises<\/strong><\/h2>\n<p>Here&#8217;s an exercise. Try picking out the hybridization of the atoms in this highly poisonous molecule made by the frog in funky looking pyjamas, below right.<\/p>\n<p>[Don&#8217;t worry if the molecule looks a little crazy: just focus on the\u00a0<strong>individual atoms<\/strong>\u00a0that the arrows point to (A, B, C, D, E). A and B especially. \u00a0If you haven&#8217;t mastered line diagrams yet (<a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/06\/27\/hidden-hydrogens-hidden-lone-pairs-hidden-counterions\/\">and &#8220;hidden&#8221; hydrogens<\/a>) maybe get some more practice and come back to this later.]<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"43634\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"43634\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"43634\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"43634\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-43634\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-43634 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"43634\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-9tnix\" data-id=\"9tnix\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2299-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2299-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>Here are some more examples.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"43635\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"43635\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"43635\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"43635\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-43635\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-43635 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"43635\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-rxo4q\" data-id=\"rxo4q\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2300-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2300-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p><span style=\"color: #993366;\"><em>More practice quizzes for hybridization can be found <a href=\"https:\/\/www.masterorganicchemistry.com\/organic-chemistry-practice-problems\/bond-hybridization-practice\/\"><span style=\"text-decoration: underline;\">here<\/span> <\/a>(MOC Membership unlocks them all)<\/em><\/span><\/p>\n<h2><strong><a id=\"three\"><\/a>3. Are There Any Exceptions?\u00a0<\/strong><\/h2>\n<p>Sure. \u00a0Although as with many things, explaining the shortcut takes about 2 minutes, while explaining the exceptions takes about 10 times longer.<\/p>\n<p>Helpfully, these exceptions fall into two main categories. It should be noted that by the time your course explains why these examples are exceptions, it will likely have moved far beyond hybridization. Phytoplankton<\/p>\n<p>Bottom line: <em>these probably won&#8217;t be found on your first midterm.<\/em><\/p>\n<h2><strong><a id=\"four\"><\/a>4. Exception #1: Lone Pairs Adjacent To Pi-bonds\u00a0<\/strong><\/h2>\n<p>The main exception is for atoms bearing lone pairs that are <strong>adjacent to pi bonds.<\/strong><\/p>\n<p><strong>Quick shortcut:<\/strong> Lone pairs adjacent to pi-bonds (and pi-systems) tend to be in <strong>unhybridized<\/strong> p orbitals, rather than in hybridized\u00a0sp<sup>n\u00a0<\/sup>orbitals.<\/p>\n<p>This is most common for\u00a0<strong>nitrogen\u00a0<\/strong>and\u00a0<strong>oxygen<\/strong>.<\/p>\n<p>In the cases below, a nitrogen or oxygen that we might expect to be <strong>sp<sup>3<\/sup><\/strong> hybridized is actually <strong>sp<sup>2<\/sup><\/strong> hybridized (trigonal planar).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14006\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/6-exceptions-to-shortcut-expected-hybridization-versus-actual-due-to-resonance-and-aromaticity.gif\" alt=\"exceptions-to-shortcut-expected-hybridization-versus-actual-due-to-resonance-and-aromaticity\" width=\"525\" height=\"353\" \/><\/p>\n<p>Why? The quick answer is that lowering of energy from\u00a0<strong>conjugation of the p-orbital with the adjacent pi-bond<\/strong> more than compensates for the rise in energy due to greater electron-pair repulsion for sp<sup>2<\/sup> versus sp<sup>3<\/sup><\/p>\n<p><span style=\"color: #993366;\"><em>[see this post: &#8220;<a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2017\/01\/24\/conjugation-and-resonance\/\">Conjugation and Resonance<\/a>&#8220;]<\/em><\/span><\/p>\n<p>What&#8217;s the long answer?<\/p>\n<h2><a id=\"five\"><\/a>5. Lone Pairs In P-Orbitals (Versus Hybrid Orbitals) Have Better Orbital Overlap With Adjacent Pi Systems<\/h2>\n<p>Let&#8217;s think back to why atoms hybridize in the first place: minimization of electron-pair repulsion.<\/p>\n<p>For a primary amine like methylamine, adoption of a tetrahedral (sp<sup>3<\/sup>) geometry by nitrogen versus a trigonal planar (sp<sup>2<\/sup>) geometry is worth about 5 kcal\/mol [<span style=\"color: #993366;\"><em>roughly 20 kJ\/mol]<\/em><\/span>.<\/p>\n<p>That might not sound like a lot, but for two species in equilibrium, a difference of 5 kcal\/mol in energy represents a ratio of about<strong> 4400:1<\/strong>\u00a0. <span style=\"color: #993366;\"><em>[How do we know this? See this (advanced) <a style=\"color: #993366;\" href=\"#notetwo\">Note 2<\/a> on nitrogen inversion]\u00a0<\/em><\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14007\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/7-amines-favor-tetrahedral-sp3-hybridized-geometrl.gif\" alt=\"amines-favor-tetrahedral-sp3-hybridized-geometrl\" width=\"495\" height=\"224\" \/><\/p>\n<p>What if there was some compensating effect whereby a lone pair in an <strong>unhybridized<\/strong> p-orbital was actually <strong>more stable<\/strong> than if it was in a hybridized orbital?<\/p>\n<p>This turns out to be the case in many situations where the lone pair is <strong>adjacent to a pi bond<\/strong>! \u00a0The most common and important example is that of <strong>amides<\/strong>, which constitute the linkages between amino acids. The nitrogen in amides is planar (sp<sup>2<\/sup>), not trigonal pyramidal (sp<sup>3<\/sup>), as proven by X-ray crystallography.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14008\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/8-why-sp2-hybridization-favored-for-amide-nitrogens-planarity-allows-delocalization-of-electrons-worth-10-kcal-mol.gif\" alt=\"why-sp2-hybridization-favored-for-amide-nitrogens-planarity-allows-delocalization-of-electrons-worth-10-kcal-mol\" width=\"525\" height=\"197\" \/><\/p>\n<p>The difference in energy varies widely, but a typical value is about 10 kcal\/mol favouring the trigonal planar geometry. <span style=\"color: #993366;\"><em>\u00a0[We know this because many amides have a measurable<strong> barrier to rotation<\/strong> &#8211;\u00a0 a topic we also talked about in the<span style=\"text-decoration: underline;\"> <a style=\"color: #993366; text-decoration: underline;\" href=\"https:\/\/www.masterorganicchemistry.com\/2017\/01\/24\/conjugation-and-resonance\/\">Conjugation and Resonance<\/a><\/span> post]<\/em><\/span><\/p>\n<p>Why is trigonal planar geometry favoured here? <strong>Better orbital overlap of the p orbital with the pi bond vs. the (hybridized) sp<sup>3<\/sup> orbital<\/strong>.<\/p>\n<p>The drawing below tries to show how a change in hybridization from sp<sup>3<\/sup> to sp<sup>2<\/sup> brings the p-orbital closer to the adjoining p-orbitals of the pi bond, allowing for better orbital overlap. Better orbital overlap allows for stronger pi-bonding between the nitrogen lone pair and the carbonyl p-orbital, which results in an overall lowering of energy.\u00a0<img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14009\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/9-sp2-hybridization-of-nitrogens-in-amides-allows-for-better-orbital-overlap.gif\" alt=\"sp2-hybridization-of-nitrogens-in-amides-allows-for-better-orbital-overlap\" width=\"525\" height=\"209\" \/><\/p>\n<p>You can think of this as leading to a stronger &#8220;partial&#8221; C\u2013N bond.\u00a0Two important consequences of this interaction are\u00a0<a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/01\/24\/conjugation-and-resonance\/\">restricted rotation<\/a> in amides, as well as the fact that acid reacts with amides on the oxygen, not the nitrogen lone pair (!)<\/p>\n<p>The oxygen in <strong>esters<\/strong> and <strong>enols<\/strong> is also also sp<sup>2<\/sup> hybridized, as is the nitrogen in <strong>enamines<\/strong> and countless other examples.<\/p>\n<p>As you will likely see in Org 2, some of the most dramatic cases are those where the &#8220;de-hybridized&#8221; lone pair participates in an <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/02\/23\/rules-for-aromaticity\/\">aromatic system<\/a>. Here, the energetic compensation for a change in hybridization from sp<sup>3<\/sup> to sp<sup>2<\/sup> can be very great indeed &#8211; more than 20 kcal\/mol in some cases.<\/p>\n<p>For this reason, the most basic site of pyrrole is not the nitrogen lone pair, but on the carbon (C-2) (!).<\/p>\n<h2><strong><a id=\"six\"><\/a>6. Exception #2. Geometric Constraints<\/strong><\/h2>\n<p>Another example where the actual hybridization differs from what we might expect from the shortcut is in cases with geometric constraints. For instance in the phenyl cation below, the indicated carbon is attached to two atoms and zero lone pairs.<\/p>\n<p>What&#8217;s the hybridization?<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14010\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/10-geometry-determines-hybridization-not-the-other-way-round-aryl-carbocation-is-sp2-hybridized.gif\" alt=\"geometry-determines-hybridization-not-the-other-way-round-aryl-carbocation-is-sp2-hybridized\" width=\"495\" height=\"294\" \/><a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2018\/01\/10-exception-constraint-e1515787498239.png\"><br \/>\n<\/a><\/p>\n<p>From our shortcut, we might expect the hybridization to be<strong> sp<\/strong>.<\/p>\n<p>In fact, the geometry around the atom is much closer to sp<sup>2<\/sup>. That&#8217;s because the angle strain adopting the linear (sp) geometry would lead to far too much angle strain to be a stable molecule.<\/p>\n<h2><a id=\"seven\"><\/a>7. &#8220;Geometry Determines Hybridization, Not The Other Way Around&#8221;<\/h2>\n<p>A quote passed on to me from <a href=\"https:\/\/www.masterorganicchemistry.com\/tutoring\/\">Matt<\/a> seems appropriate:<\/p>\n<p><em>&#8220;Geometry determines hybridization, not the other way around&#8221;<\/em><\/p>\n<p>Well, that&#8217;s probably more than you wanted to know about how to determine the hybridization of atoms.<\/p>\n<p>Suffice to say, any post from this site that contains shortcut in the title is a sure fire-bet to have over 1000 words and &gt;10 figures.<\/p>\n<p><strong>Thanks to Matt Pierce of\u00a0<a href=\"http:\/\/organicchemistrysolutions.com\">Organic Chemistry Solutions\u00a0<\/a>\u00a0for important contributions to this post. \u00a0Ask Matt about scheduling an online tutoring session\u00a0<a href=\"https:\/\/masterorganic.wufoo.com\/forms\/q1yg3qx8076h7gx\/\">here<\/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\/2011\/06\/27\/hidden-hydrogens-hidden-lone-pairs-hidden-counterions\/\" class=\"\"><span>Hidden Hydrogens, Hidden Lone Pairs, Hidden Counterions<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/10\/10\/hybrid-orbitals\/\" class=\"\"><span>Hybrid Orbitals and Hybridization<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/08\/25\/how-do-we-know-methane-is-tetrahedral\/\" class=\"\"><span>How Do We Know Methane (CH4) Is Tetrahedral?<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/01\/19\/hybridization-and-bond-strengths\/\" class=\"\"><span>Orbital Hybridization And Bond Strengths<\/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\/organic-chemistry-practice-problems\/bond-hybridization-practice\/\" class=\"\"><span>Bond Hybridization Practice (MOC Membership)<\/span><\/a><\/li><\/ul><\/div>\n<p><strong><a id=\"noteone\"><\/a>Note 1. Some weird cases.<\/strong><\/p>\n<p>Sometimes you might be asked to determine the hybridization of\u00a0<strong>free radicals<\/strong> and of\u00a0<strong>carbenes\u00a0<\/strong>(or nitrenes)<\/p>\n<p>Although you&#8217;re unlikely to encounter these, let&#8217;s still have a look.<\/p>\n<ul>\n<li>Free radicals exist in a <strong>shallow pyramidal\u00a0<\/strong>geometry, not purely sp<sup>2<\/sup> or sp<sup>3<\/sup>.<\/li>\n<li>However, if they are\u00a0<strong>adjacent<\/strong> to a pi system (e.g. a C-C double or triple bond) then the shallow pyramid will\u00a0<strong>re-hybridize<\/strong> to give it an sp<sup>2<\/sup> geometry, which allows for full <strong>resonance delocalization<\/strong> of the free radical.<\/li>\n<li><strong>Carbenes<\/strong> and\u00a0<strong>nitrenes<\/strong> would give us sp<sup>2<\/sup> geometry by the hybridization shortcut. However their actual structures can vary depending on whether or not the electron pair exists in a single orbital (a\u00a0<strong>singlet<\/strong> carbene) or is divided into two singly-filled orbitals\u00a0(a\u00a0<strong>triplet<\/strong> carbene). That&#8217;s really beyond the scope of introductory organic chemistry.<\/li>\n<\/ul>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14011\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/F1-hybridization-of-free-radicals-is-shallow-pyramidal-not-purely-sp3-carbenes-nitrenes-sp2-hybridization.gif\" alt=\" F1-hybridization-of-free-radicals-is-shallow-pyramidal-not-purely-sp3-carbenes-nitrenes-sp2-hybridization\" width=\"525\" height=\"410\" \/><\/p>\n<p>What about higher block elements like sulfur and phosphorus?<\/p>\n<p>Third row elements like phosphorus and sulfur can exceed an octet of electrons by incorporating d-orbitals in the hybrid. \u00a0This is more in the realm of inorganic chemistry so I don&#8217;t really want to discuss it. Here&#8217;s an example for the hybridization of SF<sub>4<\/sub> from <a href=\"https:\/\/chem.libretexts.org\/LibreTexts\/Mount_Royal_University\/Chem_1201\/Unit_4%3A_Chemical_Bonding_II_-_Advanced_Bonding_Theories\/4.06%3A_Hybridization_using_d_Orbitals\">elsewhere<\/a>. \u00a0(sp<sup>3<\/sup>d orbitals).<\/p>\n<p><a id=\"notetwo\"><\/a><strong>Note 2<\/strong>: For the 5 kcal\/mol figure, <a href=\"#reftwo\">see here<\/a>. [Tetrahedron Lett, 1971, <em>37<\/em>, 3437].<em> (Kurt Mislow, <a href=\"https:\/\/www.princeton.edu\/news\/2017\/10\/27\/kurt-mislow-pioneer-stereochemistry-dies-94\">RIP<\/a>. )<\/em><\/p>\n<p>An amine connected to three different substituents (R<sup>1<\/sup> R<sup>2<\/sup> and R<sup>3<\/sup>) should be chiral, since it has in total 4 different substituents (including the lone pair). However, all early attempts to prepare enantiomerically pure amines met with failure. It was later found that amines undergo <strong>inversion<\/strong> at room temperature, like an umbrella being forced inside-out by a strong wind.<\/p>\n<p>In the transition state for inversion the nitrogen is trigonal planar. One can thus calculate the difference in energy between the sp<sup>3<\/sup> and sp<sup>2<\/sup> geometries by measuring the activation barrier for this process (see <a href=\"#refone\">ref<\/a>).<\/p>\n<p><strong><a id=\"notethree\"><\/a>Note 3<\/strong>:A fun counter-example might be <a href=\"https:\/\/en.wikipedia.org\/wiki\/Coelenterazine\">Coelenterazine<\/a>\u00a0.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14012\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/F2-coelenterazine-hybridization-of-orbitals.gif\" alt=\"F2-coelenterazine-hybridization-of-orbitals\" width=\"525\" height=\"278\" \/><\/p>\n<p>One would not expect both nitrogen atoms to be sp<sup>2<\/sup> hybridized, because that would lead to a cyclic, flat, conjugated system with 8 pi electrons : in other words, <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/03\/27\/antiaromaticity\/\">antiaromatic.<\/a> I can&#8217;t find a crystal structure of the core molecule to confirm (but would welcome any additional information!)<\/p>\n<p>NOTE &#8211; (added afterwards) If you draw the resonance form where the nitrogen lone pair forms a pi bond with the carbonyl carbon, then the ring system has 10 electrons and would therefore be &#8220;aromatic&#8221;.<\/p>\n<h2><a id=\"quiz\"><\/a>Quiz Yourself!<\/h2>\n<p>&nbsp;<\/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\/0328-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\/0652-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\/0325-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\/2503-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\/3032-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<p>&nbsp;<\/p>\n<hr \/>\n<ol class=\"downloadCitList\">\n<li><strong><a id=\"refone\"><\/a>Barrier to pyramidal inversion of nitrogen in dibenzylmethylamine<\/strong><br \/>\nMichael J. S. Dewar and W. Brian Jennings<br \/>\n<cite>Journal of the American Chemical Society<\/cite>\u00a0<strong>1971<\/strong>\u00a0<em>93<\/em> (2), 401-403<br \/>\n<strong>DOI:<\/strong> <a href=\"https:\/\/doi.org\/10.1021\/ja00731a016\">10.1021\/ja00731a016<\/a><\/li>\n<li>\n<p id=\"screen-reader-main-title\" class=\"Head u-font-serif u-h2 u-margin-s-ver\"><strong><span class=\"title-text\"><a id=\"reftwo\"><\/a>Pyramidal inversion barriers: the significance of ground state geometry<br \/>\n<\/span><\/strong><span class=\"title-text\">Joseph Stackhouse, Raymond D.Baechler, Kurt Mislow<br \/>\n<em>Tetrahedron Letters\u00a0 <\/em>Volume 12, Issue 37,\u00a0<strong>1971<\/strong>, Pages 3437-3440<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/doi.org\/10.1016\/S0040-4039(01)97199-0\">doi.org\/10.1016\/S0040-4039(01)97199-0<\/a><\/span><strong><span class=\"title-text\"><br \/>\n<\/span><\/strong><\/p>\n<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>A Shortcut For Determining The Hybridization Of An Atom In A Molecule Here&#8217;s a shortcut for how to determine the hybridization of an atom in <\/p>\n","protected":false},"author":1,"featured_media":26357,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1406],"tags":[320,1291,399,1292,615,678,679],"post_folder":[],"class_list":["post-11195","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-bonding-structure-resonance","tag-aromaticity","tag-hybrid-shortcut","tag-hybridization","tag-nitrogen-inversion","tag-sp","tag-sp2","tag-sp3"],"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 Determine Hybridization: A Shortcut &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"So how do you quickly determine the hybridization of an atom? Here&#039;s a shortcut that works in 95% of cases (we also cover the exceptions, and show examples)\" \/>\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\/2018\/01\/16\/a-hybridization-shortcut\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"How To Determine Hybridization: A Shortcut &#8211; Master Organic Chemistry\" \/>\n<meta property=\"og:description\" content=\"So how do you quickly determine the hybridization of an atom? Here&#039;s a shortcut that works in 95% of cases (we also cover the exceptions, and show examples)\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.masterorganicchemistry.com\/2018\/01\/16\/a-hybridization-shortcut\/\" \/>\n<meta property=\"og:site_name\" content=\"Master Organic Chemistry\" \/>\n<meta property=\"article:publisher\" content=\"https:\/\/www.facebook.com\/Master-Organic-Chemistry-242610599108055\/\" \/>\n<meta property=\"article:published_time\" content=\"2018-01-16T13:00:41+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2026-04-18T02:14:33+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2018\/01\/0-tips-for-determining-hybridization-of-molecules.gif\" \/>\n\t<meta property=\"og:image:width\" content=\"896\" \/>\n\t<meta property=\"og:image:height\" content=\"730\" \/>\n\t<meta property=\"og:image:type\" content=\"image\/gif\" \/>\n<meta name=\"author\" content=\"James Ashenhurst\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"James Ashenhurst\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"12 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\\\/\\\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2018\\\/01\\\/16\\\/a-hybridization-shortcut\\\/#article\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2018\\\/01\\\/16\\\/a-hybridization-shortcut\\\/\"},\"author\":{\"name\":\"James Ashenhurst\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/person\\\/78d83ec7d02b4b7365bade2cedaef80c\"},\"headline\":\"How To Determine Hybridization: A Shortcut\",\"datePublished\":\"2018-01-16T13:00:41+00:00\",\"dateModified\":\"2026-04-18T02:14:33+00:00\",\"mainEntityOfPage\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2018\\\/01\\\/16\\\/a-hybridization-shortcut\\\/\"},\"wordCount\":1858,\"commentCount\":46,\"publisher\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#organization\"},\"image\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2018\\\/01\\\/16\\\/a-hybridization-shortcut\\\/#primaryimage\"},\"thumbnailUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2018\\\/01\\\/0-tips-for-determining-hybridization-of-molecules.gif\",\"keywords\":[\"aromaticity\",\"hybrid shortcut\",\"hybridization\",\"nitrogen inversion\",\"sp\",\"sp2\",\"sp3\"],\"articleSection\":[\"Bonding, Structure, and Resonance\"],\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"CommentAction\",\"name\":\"Comment\",\"target\":[\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2018\\\/01\\\/16\\\/a-hybridization-shortcut\\\/#respond\"]}]},{\"@type\":\"WebPage\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2018\\\/01\\\/16\\\/a-hybridization-shortcut\\\/\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2018\\\/01\\\/16\\\/a-hybridization-shortcut\\\/\",\"name\":\"How To Determine Hybridization: A Shortcut &#8211; Master Organic Chemistry\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#website\"},\"primaryImageOfPage\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2018\\\/01\\\/16\\\/a-hybridization-shortcut\\\/#primaryimage\"},\"image\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2018\\\/01\\\/16\\\/a-hybridization-shortcut\\\/#primaryimage\"},\"thumbnailUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2018\\\/01\\\/0-tips-for-determining-hybridization-of-molecules.gif\",\"datePublished\":\"2018-01-16T13:00:41+00:00\",\"dateModified\":\"2026-04-18T02:14:33+00:00\",\"description\":\"So how do you quickly determine the hybridization of an atom? Here's a shortcut that works in 95% of cases (we also cover the exceptions, and show examples)\",\"breadcrumb\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2018\\\/01\\\/16\\\/a-hybridization-shortcut\\\/#breadcrumb\"},\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"ReadAction\",\"target\":[\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2018\\\/01\\\/16\\\/a-hybridization-shortcut\\\/\"]}]},{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2018\\\/01\\\/16\\\/a-hybridization-shortcut\\\/#primaryimage\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2018\\\/01\\\/0-tips-for-determining-hybridization-of-molecules.gif\",\"contentUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2018\\\/01\\\/0-tips-for-determining-hybridization-of-molecules.gif\",\"width\":896,\"height\":730,\"caption\":\"-tips for determining hybridization of molecules\"},{\"@type\":\"BreadcrumbList\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2018\\\/01\\\/16\\\/a-hybridization-shortcut\\\/#breadcrumb\",\"itemListElement\":[{\"@type\":\"ListItem\",\"position\":1,\"name\":\"Home\",\"item\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/\"},{\"@type\":\"ListItem\",\"position\":2,\"name\":\"How To Determine Hybridization: A Shortcut\"}]},{\"@type\":\"WebSite\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#website\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/\",\"name\":\"Master Organic Chemistry\",\"description\":\"\",\"publisher\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#organization\"},\"potentialAction\":[{\"@type\":\"SearchAction\",\"target\":{\"@type\":\"EntryPoint\",\"urlTemplate\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/?s={search_term_string}\"},\"query-input\":{\"@type\":\"PropertyValueSpecification\",\"valueRequired\":true,\"valueName\":\"search_term_string\"}}],\"inLanguage\":\"en-US\"},{\"@type\":\"Organization\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#organization\",\"name\":\"Master Organic Chemistry\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/\",\"logo\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/logo\\\/image\\\/\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2019\\\/04\\\/cutmypic.png\",\"contentUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2019\\\/04\\\/cutmypic.png\",\"width\":225,\"height\":225,\"caption\":\"Master Organic Chemistry\"},\"image\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/logo\\\/image\\\/\"},\"sameAs\":[\"https:\\\/\\\/www.facebook.com\\\/Master-Organic-Chemistry-242610599108055\\\/\"]},{\"@type\":\"Person\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/person\\\/78d83ec7d02b4b7365bade2cedaef80c\",\"name\":\"James Ashenhurst\",\"image\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/secure.gravatar.com\\\/avatar\\\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g\",\"url\":\"https:\\\/\\\/secure.gravatar.com\\\/avatar\\\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g\",\"contentUrl\":\"https:\\\/\\\/secure.gravatar.com\\\/avatar\\\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g\",\"caption\":\"James Ashenhurst\"},\"description\":\"Ph.D. 2006, McGill University (James L. Gleason). Postdoctoral Associate, 2008-2010, Massachusetts Institute of Technology (M. Movassaghi). Founder, Master Organic Chemistry, 2010-present.\",\"sameAs\":[\"https:\\\/\\\/www.masterorganicchemistry.com\\\/about\\\/\"],\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/author\\\/james\\\/\"}]}<\/script>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"How To Determine Hybridization: A Shortcut &#8211; Master Organic Chemistry","description":"So how do you quickly determine the hybridization of an atom? Here's a shortcut that works in 95% of cases (we also cover the exceptions, and show examples)","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/www.masterorganicchemistry.com\/2018\/01\/16\/a-hybridization-shortcut\/","og_locale":"en_US","og_type":"article","og_title":"How To Determine Hybridization: A Shortcut &#8211; Master Organic Chemistry","og_description":"So how do you quickly determine the hybridization of an atom? Here's a shortcut that works in 95% of cases (we also cover the exceptions, and show examples)","og_url":"https:\/\/www.masterorganicchemistry.com\/2018\/01\/16\/a-hybridization-shortcut\/","og_site_name":"Master Organic Chemistry","article_publisher":"https:\/\/www.facebook.com\/Master-Organic-Chemistry-242610599108055\/","article_published_time":"2018-01-16T13:00:41+00:00","article_modified_time":"2026-04-18T02:14:33+00:00","og_image":[{"width":896,"height":730,"url":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2018\/01\/0-tips-for-determining-hybridization-of-molecules.gif","type":"image\/gif"}],"author":"James Ashenhurst","twitter_card":"summary_large_image","twitter_misc":{"Written by":"James Ashenhurst","Est. reading time":"12 minutes"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"Article","@id":"https:\/\/www.masterorganicchemistry.com\/2018\/01\/16\/a-hybridization-shortcut\/#article","isPartOf":{"@id":"https:\/\/www.masterorganicchemistry.com\/2018\/01\/16\/a-hybridization-shortcut\/"},"author":{"name":"James Ashenhurst","@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/person\/78d83ec7d02b4b7365bade2cedaef80c"},"headline":"How To Determine Hybridization: A Shortcut","datePublished":"2018-01-16T13:00:41+00:00","dateModified":"2026-04-18T02:14:33+00:00","mainEntityOfPage":{"@id":"https:\/\/www.masterorganicchemistry.com\/2018\/01\/16\/a-hybridization-shortcut\/"},"wordCount":1858,"commentCount":46,"publisher":{"@id":"https:\/\/www.masterorganicchemistry.com\/#organization"},"image":{"@id":"https:\/\/www.masterorganicchemistry.com\/2018\/01\/16\/a-hybridization-shortcut\/#primaryimage"},"thumbnailUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2018\/01\/0-tips-for-determining-hybridization-of-molecules.gif","keywords":["aromaticity","hybrid shortcut","hybridization","nitrogen inversion","sp","sp2","sp3"],"articleSection":["Bonding, Structure, and Resonance"],"inLanguage":"en-US","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.masterorganicchemistry.com\/2018\/01\/16\/a-hybridization-shortcut\/#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.masterorganicchemistry.com\/2018\/01\/16\/a-hybridization-shortcut\/","url":"https:\/\/www.masterorganicchemistry.com\/2018\/01\/16\/a-hybridization-shortcut\/","name":"How To Determine Hybridization: A Shortcut &#8211; Master Organic Chemistry","isPartOf":{"@id":"https:\/\/www.masterorganicchemistry.com\/#website"},"primaryImageOfPage":{"@id":"https:\/\/www.masterorganicchemistry.com\/2018\/01\/16\/a-hybridization-shortcut\/#primaryimage"},"image":{"@id":"https:\/\/www.masterorganicchemistry.com\/2018\/01\/16\/a-hybridization-shortcut\/#primaryimage"},"thumbnailUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2018\/01\/0-tips-for-determining-hybridization-of-molecules.gif","datePublished":"2018-01-16T13:00:41+00:00","dateModified":"2026-04-18T02:14:33+00:00","description":"So how do you quickly determine the hybridization of an atom? Here's a shortcut that works in 95% of cases (we also cover the exceptions, and show examples)","breadcrumb":{"@id":"https:\/\/www.masterorganicchemistry.com\/2018\/01\/16\/a-hybridization-shortcut\/#breadcrumb"},"inLanguage":"en-US","potentialAction":[{"@type":"ReadAction","target":["https:\/\/www.masterorganicchemistry.com\/2018\/01\/16\/a-hybridization-shortcut\/"]}]},{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.masterorganicchemistry.com\/2018\/01\/16\/a-hybridization-shortcut\/#primaryimage","url":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2018\/01\/0-tips-for-determining-hybridization-of-molecules.gif","contentUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2018\/01\/0-tips-for-determining-hybridization-of-molecules.gif","width":896,"height":730,"caption":"-tips for determining hybridization of molecules"},{"@type":"BreadcrumbList","@id":"https:\/\/www.masterorganicchemistry.com\/2018\/01\/16\/a-hybridization-shortcut\/#breadcrumb","itemListElement":[{"@type":"ListItem","position":1,"name":"Home","item":"https:\/\/www.masterorganicchemistry.com\/"},{"@type":"ListItem","position":2,"name":"How To Determine Hybridization: A Shortcut"}]},{"@type":"WebSite","@id":"https:\/\/www.masterorganicchemistry.com\/#website","url":"https:\/\/www.masterorganicchemistry.com\/","name":"Master Organic Chemistry","description":"","publisher":{"@id":"https:\/\/www.masterorganicchemistry.com\/#organization"},"potentialAction":[{"@type":"SearchAction","target":{"@type":"EntryPoint","urlTemplate":"https:\/\/www.masterorganicchemistry.com\/?s={search_term_string}"},"query-input":{"@type":"PropertyValueSpecification","valueRequired":true,"valueName":"search_term_string"}}],"inLanguage":"en-US"},{"@type":"Organization","@id":"https:\/\/www.masterorganicchemistry.com\/#organization","name":"Master Organic Chemistry","url":"https:\/\/www.masterorganicchemistry.com\/","logo":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/logo\/image\/","url":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/04\/cutmypic.png","contentUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/04\/cutmypic.png","width":225,"height":225,"caption":"Master Organic Chemistry"},"image":{"@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/logo\/image\/"},"sameAs":["https:\/\/www.facebook.com\/Master-Organic-Chemistry-242610599108055\/"]},{"@type":"Person","@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/person\/78d83ec7d02b4b7365bade2cedaef80c","name":"James Ashenhurst","image":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/secure.gravatar.com\/avatar\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g","contentUrl":"https:\/\/secure.gravatar.com\/avatar\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g","caption":"James Ashenhurst"},"description":"Ph.D. 2006, McGill University (James L. Gleason). Postdoctoral Associate, 2008-2010, Massachusetts Institute of Technology (M. Movassaghi). Founder, Master Organic Chemistry, 2010-present.","sameAs":["https:\/\/www.masterorganicchemistry.com\/about\/"],"url":"https:\/\/www.masterorganicchemistry.com\/author\/james\/"}]}},"_links":{"self":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/posts\/11195","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/comments?post=11195"}],"version-history":[{"count":0,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/posts\/11195\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/media\/26357"}],"wp:attachment":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/media?parent=11195"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/categories?post=11195"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/tags?post=11195"},{"taxonomy":"post_folder","embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/post_folder?post=11195"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}