{"id":11238,"date":"2018-01-19T14:24:10","date_gmt":"2018-01-19T20:24:10","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=11238"},"modified":"2026-05-06T19:23:23","modified_gmt":"2026-05-07T00:23:23","slug":"hybridization-and-bond-strengths","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2018\/01\/19\/hybridization-and-bond-strengths\/","title":{"rendered":"Orbital Hybridization And Bond Strengths"},"content":{"rendered":"<p><strong>How Orbital Hybridization Affects Bond Strengths<\/strong><\/p>\n<p>Understanding the concept of hybrid orbitals (<a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/10\/10\/orbital-hybridization-post\/\"><em>see previous post<\/em><\/a>) <strong>lets you make accurate predictions about trends in bond strengths<\/strong>. In this post we&#8217;ll give several examples of how to do this.<\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-38652\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/12\/0-summary-greater-s-character-tends-to-result-in-stronger-bonds-sp-stronger-than-sp2-stronger-than-sp3.gif\" alt=\"summary greater s character tends to result in stronger bonds sp stronger than sp2 stronger than sp3\" width=\"640\" height=\"685\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">A Quick Quiz (On Bond Dissociation Energy)<\/a><\/li>\n<li><a href=\"#two\">Key Principle On Orbital Hybridization And Bond Strengths: The Greater The s-character, The Stronger The Bond<\/a><\/li>\n<li><a href=\"#three\">Electrons In <i>s<\/i>-Orbitals Are Closer To the Nucleus Than Electrons In The Corresponding p-Orbitals<\/a><\/li>\n<li><a href=\"#four\">Summary: All Else Being Equal, The Greater The s-Character, The Stronger The Bond<\/a><\/li>\n<li><a href=\"#five\">Bonus Section: An Answer To A Question A Few People Might Be Asking<\/a><\/li>\n<li><a href=\"#six\">Homolytic versus Heterolytic Bond Cleavage<\/a><\/li>\n<li><a href=\"#seven\">A Test For You<\/a><\/li>\n<li><a href=\"#eight\">One Last Thing: This Concept Also Explains Why CH<span class=\"s2\"><sub>3<\/sub><\/span><span class=\"s1\">+ Is More Stable Than NH<\/span><span class=\"s2\"><sub>3<\/sub><\/span><span class=\"s1\">+\u00a0<\/span><\/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><a id=\"one\"><\/a>1. A Quick Quiz<\/h2>\n<p>Let&#8217;s start with a quick quiz.<\/p>\n<p>What&#8217;s the strongest C\u2013H bond, below?<\/p>\n<p><em>(In other words, which C\u2013H bond has the highest bond-dissociation energy?)\u00a0<\/em><\/p>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14013\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/1-quiz-which-c-h-bond-has-highest-bond-dissociation-energy-sp3-c-h-sp2-c-h-or-sp-c-h-105-vs-110-vs-126-kcal-mol.gif\" alt=\"quiz - which ch bond has the highest bond dissociation energy\" width=\"630\" height=\"192\" \/><\/p>\n<p>The answer is C.<\/p>\n<ul>\n<li>In a), the carbon is sp<sup>3<\/sup> hybridized and the bond dissociation energy is 105 kcal\/mol<\/li>\n<li>In b), the carbon is sp<sup>2<\/sup> hybridized and the bond dissociation energy is 110 kcal\/mol<\/li>\n<li>In c), the carbon is sp hybridized and the bond dissociation energy is 126 kcal\/mol<\/li>\n<\/ul>\n<h2><strong><a id=\"two\"><\/a>2. Key Principle On Orbital Hybridization And Bond Strengths: The Greater The s-character, The Stronger The Bond<\/strong><\/h2>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14014\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/2-the-greater-the-s-character-of-a-bond-the-stronger-it-is-so-sp-stronger-than-sp2-stronger-than-sp3.gif\" alt=\"the-greater-the-s-character-of-a-bond-the-stronger-it-is-so-sp-stronger-than-sp2-stronger-than-sp3\" width=\"630\" height=\"213\" \/><\/p>\n<p>Note that the trend for bond strengths, above, is sp &gt; sp<sup>2<\/sup> &gt; sp<sup>3<\/sup><\/p>\n<p>In other words, the <strong>more s-character on carbon, the stronger the bond.<\/strong><\/p>\n<p>Let&#8217;s try this again. What about these three C\u2013C bonds?<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14015\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/3-which-c-c-bond-has-highest-bond-dissociation-energy-sp-sp3-sp2-sp3-or-sp3-sp3.gif\" alt=\"which-c-c-bond-has-highest-bond-dissociation-energy-sp-sp3-sp2-sp3-or-sp3-sp3\" width=\"630\" height=\"235\" \/><\/p>\n<p>Hopefully you ranked them A &gt; B &gt; C .<\/p>\n<p><strong>\u00a0All else being equal: an sp-sp<sup>3<\/sup> bond is stronger than an sp<sup>2<\/sup>-sp<sup>3<\/sup> bond,\u00a0\u00a0<\/strong><strong>which in turn is stronger than an sp<sup>3<\/sup>-sp<sup>3<\/sup> bond.<\/strong><\/p>\n<p><strong>Why?<\/strong><\/p>\n<h2><a id=\"three\"><\/a>3. Electrons In <em>s<\/em>-Orbitals Are Closer To the Nucleus Than Electrons In The Corresponding p-Orbitals<\/h2>\n<p>On average:\u00a0 electrons in <em>s<\/em> orbitals are closer to the nucleus (and therefore feel a greater effective positive charge) than electrons in the corresponding <em>p<\/em>\u00a0orbitals.<\/p>\n<p>Electrons in an sp orbital (50% s-character) will therefore experience a greater attractive force to the nucleus than electrons in an sp<sup>2<\/sup> (33% s-character) or sp<sup>3<\/sup> (25% s-character) orbital.<\/p>\n<p>&#8220;Bond dissociation energy&#8221; (BDE) mentioned above, is a measure of the energy required for\u00a0<em>homolytic<\/em> cleavage of a bond (<em>homo<\/em> = same;\u00a0<em>lysis\u00a0<\/em>= breaking). <span style=\"color: #800080;\">[See post: <em><a style=\"color: #800080;\" href=\"https:\/\/www.masterorganicchemistry.com\/2010\/06\/25\/bond-dissociation-energies-homolytic-cleavage\/\">Bond Dissociation Energies = Homolytic Cleavage<\/a><\/em>]<\/span><\/p>\n<p>That is, it measures the energy required for breakage of the bond such that each atom ends up with the same number of electrons, such as the reactions below:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14016\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/4-bond-dissociation-energy-measures-homolytic-bond-cleavage-so-alkyl-radicals-more-stable-than-alkynyl.gif\" alt=\"bond-dissociation-energy-measures-homolytic-bond-cleavage-so-alkyl-radicals-more-stable-than-alkynyl\" width=\"630\" height=\"508\" \/><\/p>\n<p>In the homolytic cleavage reactions above, a single electron is\u00a0<em>removed<\/em> from the C\u2013H molecular orbital and placed on hydrogen, which dissociates. The other electron remains on carbon.<\/p>\n<p><strong>The bond dissociation energy for the sp\u2013H bond is higher than that for sp<sup>3<\/sup>\u2013H because more force (energy) is required to remove an electron from the more tightly-held sp\u2013H molecular orbital and place it exclusively on the hydrogen atom.<\/strong><\/p>\n<p>So electrons in an orbital with more s character will be closer to the nucleus and feel a stronger electrostatic force.<\/p>\n<p>This helps to explain the higher bond energy.<\/p>\n<p><strong>Recognizing the\u00a0type of bonds in molecules is a key skill.\u00a0<\/strong>(<em>see also:<\/em> <strong><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/10\/13\/sigma-bonds-come-in-six-varieties-pi-bonds-come-in-one\/\">C-C sigma bonds come in six varieties, C-C pi bonds come in one<\/a><\/strong>).<\/p>\n<p>For most purposes, \u00a0this ends the key lesson of the post.<\/p>\n<h2><strong><a id=\"four\"><\/a>4. Summary: All Else Being Equal, The Greater The s-Character, The Stronger The Bond<\/strong><\/h2>\n<p>But&#8230; if you find yourself trying to reconcile an apparent contradiction that comes from another part of the course, read on.<\/p>\n<hr \/>\n<h2><strong><a id=\"five\"><\/a>5. Bonus Section: An Answer To A Question A Few People Might Be Asking<\/strong><\/h2>\n<p>Alkynes (pK<sub>a<\/sub> 25) are stronger acids than typical alkanes (pK<sub>a<\/sub> &gt; 50).<\/p>\n<p>For example, alkynes are readily deprotonated by strong bases such as NaNH<sub>2<\/sub>, whereas alkanes are not:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-27057\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2018\/01\/F1-if-alkyl-c-h-bonds-are-weaker-than-alkynyl-c-h-bonds-then-why-are-alkyne-c-h-so-basic.gif\" alt=\"-if alkyl c -h bonds are weaker than alkynyl c h bonds then why are alkyne c h so basic\" width=\"615\" height=\"345\" \/><\/a><\/p>\n<p>Why? Because the C\u2013H bond in an alkyne has <strong>more <em>s<\/em>-character<\/strong>, and the resulting lone pair on carbon is held <strong>more tightly<\/strong> to the nucleus, rendering the conjugate base <strong>more stable<\/strong>.<\/p>\n<p>Oh dear. There seems to be an angry mob approaching.<\/p>\n<p><span style=\"color: #993366;\"><strong><em>WAIT!<\/em>\u00a0<\/strong><em>You just said that alkyne C\u2013H bonds are <span style=\"text-decoration: underline;\">stronger<\/span> than alkane C\u2013H bonds\u00a0because they have more s-character and now you are saying that they are <span style=\"text-decoration: underline;\">easier to break<\/span>\u00a0because they have more s-character.<\/em><\/span><\/p>\n<p><span style=\"color: #993366;\"><em>Shouldn&#8217;t that make alkynes\u00a0<strong>less<\/strong><\/em><em> acidic because the C\u2013H bonds have more s-character?<\/em><\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14018\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/F2-south-park-mob-asking-why-alkynes-are-so-acidic.gif\" alt=\"F2-south-park-mob-asking-why-alkynes-are-so-acidic\" width=\"275\" height=\"206\" \/><\/p>\n<p>Put away the pitchforks! There is a perfectly logical explanation for this!<\/p>\n<h2><strong><a id=\"six\"><\/a>6. Homolytic versus Heterolytic Bond Cleavage\u00a0<\/strong><\/h2>\n<p>What&#8217;s the source of the confusion here?<\/p>\n<p>Let&#8217;s follow the electrons.<\/p>\n<p>Ultimately the resolution to this dilemma is recognizing the difference between\u00a0<em><strong>homolytic<\/strong>\u00a0<\/em>cleavage (which is what bond dissociation energy measures) and\u00a0<em><strong>heterolytic<\/strong>\u00a0<\/em>cleavage (which is what occurs in an acid-base reaction, the loss of H+ ).<\/p>\n<p>Let&#8217;s look at these two processes.<\/p>\n<p>In homolytic cleavage of a C\u2013H bond, an electron is completely removed from the vicinity of the carbon and placed on hydrogen. Because of the greater s-character of the bond, \u00a0it is more difficult to remove an electron from an sp-hybridized carbon than from an sp<sup>3<\/sup> hybridized carbon. As we said above, that&#8217;s why the bond-dissociation energies for alkyne C\u2013H bonds are higher than for alkane C\u2013H bonds.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14019\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/F3-follow-electrons-bond-dissociation-energies-measure-homolytic-bond-cleavage-this-gives-alkynyl-radical.gif\" alt=\"F3-follow-electrons-bond-dissociation-energies-measure-homolytic-bond-cleavage-this-gives-alkynyl-radical\" width=\"630\" height=\"342\" \/>In an acid-base reaction, the C\u2013H bond also breaks, but it breaks in such a way that the pair of electrons stays on the carbon atom. Since the bond breaks in a way that leads to an <em>uneven<\/em> distribution of electrons, it is called\u00a0<em>heterolytic\u00a0<\/em>bond cleavage (<em>hetero = different, lysis = breaking).\u00a0<\/em><\/p>\n<p>Let&#8217;s say that again: in an acid base reaction, \u00a0<strong>the pair of electrons stays on carbon<\/strong>, resulting in a negatively-charged carbon atom (a \u00a0&#8220;carbanion&#8221;).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14020\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/F4-acid-base-reactions-involve-heterolytic-bond-cleavage-alkynes-have-more-stable-conjugate-base.gif\" alt=\"F4-acid-base-reactions-involve-heterolytic-bond-cleavage-alkynes-have-more-stable-conjugate-base\" width=\"630\" height=\"335\" \/><\/p>\n<p>Acidity, as measured by pK<sub>a<\/sub>, is a measure of the equilibrium between an acid and its conjugate base. The more that the equilibrium favours the conjugate base, the lower the pK<sub>a<\/sub> and the stronger the acid. In other words:<\/p>\n<p><strong>Any factor which makes the conjugate base more stable, increases acidity<\/strong>.<\/p>\n<ul>\n<li>In the conjugate base of an alkyne, the lone pair is held in an sp- orbital with 50% s-character.<\/li>\n<li><span style=\"line-height: 1.5;\">In the conjugate base of an alkane, the lone pair is held in an sp<\/span><sup>3<\/sup><span style=\"line-height: 1.5;\"> orbital with 25% s-character.\u00a0<\/span><\/li>\n<\/ul>\n<p>What lone pair will be more stable?<\/p>\n<p><strong>The lone pair held more tightly to the nucleus &#8211; that is, the sp-orbital.\u00a0<\/strong><\/p>\n<p>That&#8217;s why alkynes are more acidic than alkanes: <strong>the conjugate base is more stable<\/strong>.<\/p>\n<p>Hopefully this makes it clearer that stronger C\u2013H bonds and greater C\u2013H acidity are two sides of the same phenomenon.<\/p>\n<p><span style=\"color: #993366;\">[You might find it helpful to think of\u00a0sp orbitals as having a greater effective electronegativity than sp<sup>2<\/sup> orbitals, which in turn have a greater electronegativity than sp<sup>3<\/sup> orbitals. So the reason for the greater acidity of alkynes relative to alkenes is not really so different than the greater acidity of H\u2013F relative to H<sub>2<\/sub>O. ]<\/span><\/p>\n<h2><a id=\"seven\"><\/a>7. A Test For You<\/h2>\n<p>At the risk of droning on, there is a third side of this phenomenon to consider.<\/p>\n<p>Homolytic cleavage can only happen one way. But there are <strong>two<\/strong> ways to draw heterolytic cleavage of a C\u2013H bond, and you might have noticed that I only showed one.<\/p>\n<p>There&#8217;s a second (albeit unlikely) way heterolytic cleavage can happen. The pair of electrons in the C\u2013H bond could migrate instead to hydrogen, not carbon, resulting in a hydride anion and a carbocation. \u00a0[Again, very unlikely, but bear with me here].<\/p>\n<p>Here&#8217;s a test I have for you. Based on everything we&#8217;ve gone through so far, which of the two products below (A or B) would be more stable?<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14021\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/F5-quiz-which-of-these-reaction-products-would-be-more-unstable-carbocation-radical-or-alkynyl-radical.gif\" alt=\"F5-quiz-which-of-these-reaction-products-would-be-more-unstable-carbocation-radical-or-alkynyl-radical\" width=\"505\" height=\"317\" \/><\/p>\n<p>Think it through.<\/p>\n<ul>\n<li>To form A, we have to remove a pair of electrons from an sp-hybridized carbon.<\/li>\n<li><span style=\"line-height: 1.5;\">To form B, we have to remove a pair of electrons from an sp<\/span><sup>3<\/sup><span style=\"line-height: 1.5;\">-hybridized carbon.\u00a0<\/span><\/li>\n<\/ul>\n<p><strong>What&#8217;s more favourable?<\/strong><\/p>\n<ul>\n<li>Reaction to give A would require removing two electrons from an sp-hybridized carbon.<\/li>\n<li><span style=\"line-height: 1.5;\">Reaction to give B would require removing two electrons from an sp<sup>3<\/sup> hybridized carbon.<\/span><\/li>\n<\/ul>\n<p>The reaction to give <strong>B<\/strong> should be much easier, because the electrons are less tightly held. \u00a0And indeed, sp<sup>3<\/sup>-hybridized carbocations have been observed and even isolated.<\/p>\n<p>In contrast, sp-hybridized carbocations such as A are extremely unstable and have never been observed directly. [<a href=\"#noteone\"><strong>Note 1<\/strong><\/a>]<\/p>\n<p>This observation is also consistent with all the observations above!<\/p>\n<h2><b><a id=\"eight\"><\/a>8. One Last Thing: This Concept Also Explains Why CH<sub>3<\/sub>+ Is More Stable Than NH<sub>3<\/sub>+\u00a0<\/b><\/h2>\n<p>As I said above, it can be helpful to think of sp-hybridized carbons as having a greater effective electronegativity than sp<sup>2<\/sup>-hybridized carbons, which in turn have greater electronegativity than sp<sup>3<\/sup> hybridized carbons. We used this to rationalize why <strong>alkynes<\/strong> are stronger acids than <strong>alkanes<\/strong>, similarly to why H-F is a stronger acid than H<sub>2<\/sub>O.<\/p>\n<p>This can also be <strong>flipped around<\/strong>, just as in our carbocation example above.<\/p>\n<p>The greater the electronegativity of the atom, the more <em>unstable<\/em> electron-deficient species become.<\/p>\n<p>This helps to explain why, for example, H<sub>3<\/sub>C+ (with six valence electrons) is\u00a0<em>much<\/em> more stable than H<sub>3<\/sub>N+ (also with six valence electrons) which in turn is\u00a0<em>far<\/em> more stable than oxygen or fluorine with six valence electrons; increasing electronegativity has the same effect on the stability of electron-deficient species as increasing s-character.<\/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\/2017\/10\/10\/hybrid-orbitals\/\" class=\"\"><span>Hybrid Orbitals and Hybridization<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/01\/16\/a-hybridization-shortcut\/\" class=\"\"><span>How To Determine Hybridization: A Shortcut<\/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\/2012\/03\/07\/7-factors-that-stabilize-positive-charge-in-organic-chemistry\/\" class=\"\"><span>7 Factors That Stabilize Positive Charge in Organic Chemistry<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/02\/27\/7-factors-that-stabilize-negative-charge-in-organic-chemistry\/\" class=\"\"><span>7 Factors that stabilize negative charge 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\/2010\/06\/25\/bond-dissociation-energies-homolytic-cleavage\/\" class=\"\"><span>Bond Dissociation Energies = Homolytic Cleavage<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/10\/28\/the-marriage-may-be-bad-but-the-divorce-still-costs-money\/\" class=\"\"><span>The Marriage May Be Bad, But the Divorce Still Costs Money<\/span><\/a><\/li><\/ul><\/div>\n<p><strong><a id=\"noteone\"><\/a>Note 1<\/strong>: Here&#8217;s a notable attempt to make sp-hybridized carbocations. The only application of helium in organic chemistry that I have ever seen.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14022\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/F6-tritiated-alkyne-beta-decay-gives-sp-hybridized-carbocation.gif\" alt=\"F6-tritiated-alkyne-beta-decay-gives-sp-hybridized-carbocation\" width=\"725\" height=\"230\" \/><\/p>\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\/3640-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\/3641-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\/3642-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\/3643-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><br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0679-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>How Orbital Hybridization Affects Bond Strengths Understanding the concept of hybrid orbitals (see previous post) lets you make accurate predictions about trends in bond strengths. <\/p>\n","protected":false},"author":1,"featured_media":38652,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1406],"tags":[1294,952,1293,332,399,344,464,345],"post_folder":[],"class_list":["post-11238","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-bonding-structure-resonance","tag-acidity-of-alkynes","tag-bond-dissociation-energy","tag-bond-strength","tag-carbocation-stability","tag-hybridization","tag-pi-bonds","tag-radical-stability","tag-sigma-bonds"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>On Hybrid Orbitals And Bond Strengths &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"How do hybrid orbitals translate into bond strength? When we look at a few worked examples, we find a handy principle to keep in mind: s-character!\" \/>\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\/19\/hybridization-and-bond-strengths\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"On Hybrid Orbitals And Bond Strengths &#8211; Master Organic Chemistry\" \/>\n<meta property=\"og:description\" content=\"How do hybrid orbitals translate into bond strength? 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