{"id":11040,"date":"2017-10-10T17:15:31","date_gmt":"2017-10-10T22:15:31","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=11040"},"modified":"2026-04-22T12:31:37","modified_gmt":"2026-04-22T17:31:37","slug":"hybrid-orbitals","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2017\/10\/10\/hybrid-orbitals\/","title":{"rendered":"Hybrid Orbitals and Hybridization"},"content":{"rendered":"<p>Today&#8217;s post is all about <strong>hybrid orbitals<\/strong>. Here&#8217;s a quick summary:<\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"aligncenter wp-image-13982\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/0-summary-of-hybrid-orbitals-sp3-sp2-and-sp-relationship-between-hybridization-and-geomertry-with-examples.gif\" alt=\"summary-of-hybrid-orbitals-sp3-sp2-and-sp-relationship-between-hybridization-and-geomertry-with-examples\" width=\"687\" height=\"518\" \/><\/p>\n<p><em><strong>[Note: This\u00a0post was co-authored with Matthew Pierce of\u00a0<a href=\"http:\/\/organicchemistrysolutions.com\">Organic Chemistry Solutions<\/a>.\u00a0 Ask Matt about scheduling an online tutoring session\u00a0<a href=\"https:\/\/masterorganic.wufoo.com\/forms\/q1yg3qx8076h7gx\/\">here<\/a>. ]<\/strong><\/em><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">What Orbitals Are Involved In The Tetrahedral Arrangement Of C-H Bonds Around Carbon In Methane (CH<sub>4<\/sub>)?<\/a><\/li>\n<li><a href=\"#two\">Hybrid Orbitals: An Explanation For Bonding At Carbon<\/a><\/li>\n<li><a href=\"#three\">A Pop Analogy: Hybrid Soda<\/a><\/li>\n<li><a href=\"#four\">sp<span class=\"s2\"><sup>3<\/sup><\/span><span class=\"s1\"><span class=\"s1\"> Hybridization Accurately Describes The Arrangement Of Atoms In (First-Row) Elements Bonded To Four Atoms&#8230;<\/span><\/span><\/a><\/li>\n<li><a href=\"#five\">&#8230;As Well As Situations Where The Number of [Atoms + Lone Pairs] Equals 4<\/a><\/li>\n<li><a href=\"#six\">sp<span class=\"s2\"><sup>2<\/sup><\/span><span class=\"s1\"><span class=\"s1\"> Hybridization<\/span><\/span><\/a><\/li>\n<li><a href=\"#seven\">sp Hybridization<\/a><\/li>\n<li><a href=\"#eight\">Summary &#8211; Hybrid Orbitals<\/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. What Orbitals Are Involved In The Tetrahedral Arrangement Of Methane (CH<sub>4<\/sub>)?<\/h2>\n<p>In the last post on the structure of methane we asked how we know that methane is tetrahedral (<span style=\"color: #993366;\"><em>See Article: <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/08\/25\/how-do-we-know-methane-is-tetrahedral\/\">How Do We Know That Methane Is Tetrahedral<\/a><\/em><\/span>).<\/p>\n<p>Based on the orbitals of carbon (2<em>s<\/em> and 2<em>p<\/em>) we might have naively expected three of the C-H bonds to line up along the x, y, and z axes, respectively, and have the other one at some arbitrary angle <em>(<span style=\"color: #993366;\">like 125\u00b0 or so<\/span>)<\/em><\/p>\n<p>But then, as so often happens in science, our beautiful intuitive hypothesis was destroyed by some annoying experimental facts:<\/p>\n<ul>\n<li>methane has no measurable dipole moment (our &#8220;reasonable&#8221; structure, below left, <em>would<\/em> be expected to have a measurable dipole moment)<\/li>\n<li>the crystal structure of diamond is tetrahedral, with identical bond lengths and angles between carbons of 109.5 degrees. This isn&#8217;t what we&#8217;d expect if we were dealing with bonds between &#8220;pure&#8221; 2<em>s<\/em> and 2<em>p<\/em> orbitals!<\/li>\n<\/ul>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-13983\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/1-why-does-methane-not-haver-h-c-h-bond-angles-of-90-degrees-if-carbon-has-2-electrons-in-a-2p-orbital-why-is-ch4-tetrahedral.gif\" alt=\"why-does-methane-not-haver-h-c-h-bond-angles-of-90-degrees-if-carbon-has-2-electrons-in-a-2p-orbital-why-is-ch4-tetrahedral\" width=\"590\" height=\"392\" \/><\/p>\n<p>In retrospect, the geometry makes sense. It happens that 109.5 degrees is the orientation that maximizes the distance between each of the four bonding pairs, and thus minimizes their repulsive interactions. In other words, the <strong>geometry<\/strong> is a direct <strong>consequence<\/strong> of &#8220;<em><strong>opposite charges attract, like charges repel<\/strong>&#8220;.<\/em><\/p>\n<p>But how do we describe the <strong>orbitals<\/strong> that are used to give that bond angle?<\/p>\n<p>This is a real chin-scratcher. They can&#8217;t be pure 2s orbitals (there&#8217;s only one 2s orbital, anyway). And they can&#8217;t be pure p orbitals, since the p orbitals are aligned at 90\u00b0 to each other.<\/p>\n<p>So what the heck kind of orbitals <strong>are<\/strong> they?<\/p>\n<h2><strong><a id=\"two\"><\/a>2. Hybrid Orbitals: An Explanation For Bonding At Carbon<\/strong><\/h2>\n<p>Linus Pauling asked this same question back in his classic treatise, the Nature of the Chemical Bond (1931) [<a href=\"http:\/\/courses.chem.psu.edu\/chem310\/ja01355a027.pdf\">pdf<\/a>] which in large measure won him the <a href=\"https:\/\/www.nobelprize.org\/prizes\/chemistry\/1954\/summary\/\">1954 Nobel Prize in Chemistry<\/a>.<\/p>\n<p>Pauling&#8217;s solution to this dilemma, which we still apply today, was the following:<\/p>\n<ul>\n<li>None of the bonding orbitals in methane are 100% s or 100% p. Instead, they are <strong>hybrid orbitals<\/strong> that each have partial <em>s<\/em> character and partial <em>p<\/em> character.<\/li>\n<li><span style=\"line-height: inherit;\">The three 2p orbitals and the single 2s orbital\u00a0<strong>hybridize<\/strong> (i.e., mix) to create four hybrid <em>sp<\/em><sup>3<\/sup> orbitals, which are arranged tetrahedrally around the central carbon atom.\u00a0<\/span><\/li>\n<li><span style=\"line-height: inherit;\">Each of the four hybrid orbitals has 25% s-character and 75% p-character.<\/span><\/li>\n<li>In the case of methane, each of these <em>sp<\/em><sup>3<\/sup> hybrid orbitals overlaps with a 1s orbital from hydrogen to form the C-H bonds<\/li>\n<\/ul>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-13984\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/2-explanation-for-identical-tetrahedral-bond-angles-in-methane-is-hybridization-of-s-and-p-orbitals-to-give-sp3.gif\" alt=\"explanation-for-identical-tetrahedral-bond-angles-in-methane-is-hybridization-of-s-and-p-orbitals-to-give-sp3\" width=\"685\" height=\"404\" \/><\/p>\n<p>I&#8217;ll be honest here. \u00a0Many students don&#8217;t like this explanation.<\/p>\n<p>Certainly, it&#8217;s confusing at first. \u00a0Why?<\/p>\n<p>I think that when we initially learn about orbitals, <strong>we intuitively think of them as containers &#8211;\u00a0<\/strong>sort of\u00a0like atomic Tupperware for holding electrons that happen to come in a variety of cutesy shapes.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-13985\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/3-fun-experiment-merging-two-pictures-of-fruit-containers.png\" alt=\"fun-experiment-merging-two-pictures-of-fruit-containers\" width=\"403\" height=\"270\" srcset=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/3-fun-experiment-merging-two-pictures-of-fruit-containers.png 593w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/3-fun-experiment-merging-two-pictures-of-fruit-containers-300x201.png 300w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/3-fun-experiment-merging-two-pictures-of-fruit-containers-320x215.png 320w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/3-fun-experiment-merging-two-pictures-of-fruit-containers-360x242.png 360w\" sizes=\"(max-width: 403px) 100vw, 403px\" \/><\/p>\n<p>Electrons, then, \u00a0can be imagined to behave like the &#8220;fruits&#8221;\u00a0 that rattle around in these containers (<em>strict\u00a0<\/em><em>limit: 2 per container!<\/em>). It&#8217;s not so surprising to our intuition when we learn that they can move from container to container within an atom or even leave the atom altogether.<\/p>\n<p>What\u00a0<strong>is<\/strong> surprising is when we open up the fridge and find that our cute little sphere- and dumbbell-shaped Tupperware containers \u00a0have <em>changed their shape and\u00a0<\/em><em>merged their properties with each other!\u00a0<\/em>\u00a0 This violates our intuition about how containers behave!<a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2017\/09\/banana-apple-hybrid.png\"><br \/>\n<\/a><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-13986\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/4-hybrid-fruit-containers-banana-and-apple-holder.png\" alt=\"hybrid-fruit-containers-banana-and-apple-holder\" width=\"400\" height=\"267\" srcset=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/4-hybrid-fruit-containers-banana-and-apple-holder.png 600w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/4-hybrid-fruit-containers-banana-and-apple-holder-300x200.png 300w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/4-hybrid-fruit-containers-banana-and-apple-holder-320x213.png 320w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/4-hybrid-fruit-containers-banana-and-apple-holder-360x240.png 360w\" sizes=\"(max-width: 400px) 100vw, 400px\" \/><\/p>\n<p>This is the quantum world, folks! \u00a0If this <em>doesn&#8217;t<\/em> mystify you&#8230; it f*&amp;king should!<\/p>\n<p>Going forward, I don&#8217;t ask that you understand or even &#8220;believe in&#8221; hybridization on a deep mathematical or theoretical level. That&#8217;s not necessary for our purposes\u00a0<em>[<span style=\"color: #993366;\">Pauling was a great teacher. You can always read the original Pauling paper, <a style=\"color: #993366;\" href=\"http:\/\/courses.chem.psu.edu\/chem310\/ja01355a027.pdf\">here<\/a>, if you choose<\/span>]<\/em><\/p>\n<p>I merely advise that you <strong>try<\/strong> to suspend your disbelief going forward, because using this hybridization model will help us rationalize a <strong>lot<\/strong> of molecular structure, geometry, and behaviour.<\/p>\n<h2><a id=\"three\"><\/a>3. A Pop Analogy: Hybrid Soda<\/h2>\n<p>Before we dive in any further, here&#8217;s what I consider to be a helpful little analogy (<a href=\"https:\/\/www.youtube.com\/watch?v=bt_fJfUrFY0&amp;feature=PlayList&amp;p=79FBC87F391FAC62&amp;index=0&amp;playnext=1\">thx,\u00a0<em>Steven<\/em><\/a>) that might help to get the point across.<\/p>\n<ul>\n<li>Imagine you have four bottles of pop: one bottle of Sprite (S) \u00a0and three bottles of Pepsi (P).<\/li>\n<li><span style=\"line-height: inherit;\">Now imagine pouring them out, mixing them all together, and then re-filling each bottle with the mixture.\u00a0<\/span><\/li>\n<li><span style=\"line-height: inherit;\">The Law of Conservation of Pop says that you still have four bottles worth of liquid. But now the pop is neither pure Sprite or pure Pepsi; it is a hybrid between the two.\u00a0<\/span><\/li>\n<li><span style=\"line-height: inherit;\">Specifically, each bottle now has 25% Sprite character and 75% Pepsi character.<\/span><\/li>\n<li>We can call this &#8220;hybrid&#8221; pop, if you like, <em>sp<\/em><sup>3<\/sup><\/li>\n<\/ul>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-13987\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/5-helpful-analogy-to-orbital-hybridization-is-hybridization-of-3-bottles-of-pepsi-with-one-of-sprite-to-give-4-bottles-with-25-per-cent-sprite.gif\" alt=\"helpful-analogy-to-orbital-hybridization-is-hybridization-of-3-bottles-of-pepsi-with-one-of-sprite-to-give-4-bottles-with-25-per-cent-sprite\" width=\"442\" height=\"333\" \/><\/p>\n<p>That&#8217;s a little bit like what has happened to our 2s and 2p orbitals. By\u00a0mixing the 2s and three 2p orbitals, we now have four orbitals which have 25% s character and 75% p character. <em>(<strong>Although, importantly, it&#8217;s the shapes of the bottles that are changing, not just the contents).<\/strong><\/em><\/p>\n<p>The final step is to arrange these four orbitals at the corners of a tetrahedron, which allows for the maximum distance between the four electron pairs\u00a0<em>(like charges repel!)<\/em><\/p>\n<p>How does this rationalization help us?<\/p>\n<ul>\n<li>It explains the tetrahedral molecular geometry of methane, with 4 identical H\u2013C\u2013H bond angles (109.5\u00b0)<\/li>\n<li>It explains the 4 identical C\u2013H bond lengths (and bond strengths) in methane<\/li>\n<li>It explains the lack of a dipole moment in methane, since the tetrahedral arrangement of the electron pairs allows for all partial charges to cancel\u00a0<span style=\"color: #999999;\"><em>(i.e. the vectors sum to zero)<\/em><\/span><\/li>\n<li>The model even helps to rationalize how certain reactions occur, which we won&#8217;t go into right now\u00a0<span style=\"color: #999999;\">\u00a0<span style=\"color: #993366;\"><em>[e.g. backside attack in the S<sub>N<\/sub>2 reaction occurs into the empty &#8220;antibonding&#8221; orbital 180\u00b0 to the bonding C\u2013H orbital, if you&#8217;ve been reading ahead]<\/em><\/span><\/span><\/li>\n<\/ul>\n<h2><a id=\"four\"><\/a>4. sp<sup>3<\/sup> Hybridization Accurately Describes The Arrangement Of Atoms In (First-Row) Elements Bonded To Four Atoms&#8230;<\/h2>\n<p>This doesn&#8217;t just apply to methane. It applies to any situation where a (first-row) element is bonded to four atoms. Obviously tetrahedral carbon is the most prominent example we will explore, but it also applies to tetrahedral nitrogen\u00a0[e.g. NH<sub>4<\/sub>(+)] and even tetrahedral boron [e.g. BF<sub>4<\/sub>(-)].<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-13988\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/6-sp3-hybridization-model-explains-bonding-in-tetrahedral-carbon-nh4-and-bf4.gif\" alt=\"sp3-hybridization-model-explains-bonding-in-tetrahedral-carbon-nh4-and-bf4\" width=\"598\" height=\"311\" \/><\/p>\n<h2><strong><a id=\"five\"><\/a>5&#8230;.As Well As Situations Where The Number of [Atoms + Lone Pairs] Equals 4<\/strong><\/h2>\n<p>The tetrahedral arrangement of the orbitals holds <strong>even when one or more pairs of electrons is a non-bonded lone pair<\/strong>\u00a0<em>(<span style=\"color: #993366;\">If you&#8217;ve run across <a style=\"color: #993366;\" href=\"https:\/\/en.wikipedia.org\/wiki\/VSEPR_theory\">VSEPR theory<\/a>, which most people have by the time that they arrive in organic chem, this shouldn&#8217;t come as a shock<\/span>.)\u00a0<\/em><\/p>\n<p>For instance, ammonia (NH<sub>3<\/sub>), the &#8220;methyl anion&#8221; (CH<sub>3<\/sub><sup>\u2013<\/sup>) and the hydronium ion (H<sub>3<\/sub>O<sup>+<\/sup>) all have a central atom with 4 pairs of electrons:\u00a0 3 pairs of bonding electrons and one pair of non-bonded electrons. As we&#8217;ve seen, the ideal geometry for arranging four pairs of electrons\u00a0 is tetrahedral, which makes the hybridization of the central atom <em>sp<\/em><sup>3<\/sup>.\u00a0 This leaves the molecule with a &#8220;piano stool&#8221; arrangement of atoms about the central atom, which we call &#8220;trigonal pyramidal&#8221; geometry.<\/p>\n<p>Another way of putting it is that the central atom has\u00a0tetrahedral\u00a0<em>orbital geometry<\/em> (<em>sp<\/em><sup>3<\/sup>) and trigonal planar\u00a0<em>molecular geometry.\u00a0<\/em><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-13989\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/7-hybridization-applies-to-central-atoms-attached-to-3-atoms-plus-a-lone-pair-eg-nh3-h3o-and-ch3-trigonal-pyramidal.gif\" alt=\"hybridization-applies-to-central-atoms-attached-to-3-atoms-plus-a-lone-pair-eg-nh3-h3o-and-ch3-trigonal-pyramidal\" width=\"589\" height=\"438\" \/><\/p>\n<p>An interesting fact is that the bond angles in these are compressed from the ideal angle of 109.5\u00b0. The H-N-H bond angles in ammonia, for instance, are 107 degrees. We rationalize this as being due to the fact that a non-bonded lone pair is more repulsive than a &#8220;normal&#8221; bonding pair &#8211; likely because it&#8217;s closer to the atom and exerts a stronger influence.<\/p>\n<p>This deviation from &#8220;ideal&#8221; bond angles is even greater in H<sub>2<\/sub>O (water) which has two lone pairs. The hybridization is still <em>sp<\/em><sup>3<\/sup>, the orbital geometry is still tetrahedral, but the shape (&#8220;molecular geometry&#8221;) of the resulting molecule is &#8220;bent&#8221;.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-13990\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/8-water-has-2-attached-atoms-plus-2-lone-pairs-but-is-still-sp3-orbitals-of-oxygen-are-sp3-hybridized.gif\" alt=\"water-has-2-attached-atoms-plus-2-lone-pairs-but-is-still-sp3-orbitals-of-oxygen-are-sp3-hybridized\" width=\"525\" height=\"225\" \/><\/p>\n<p>Indeed, <strong>one of the notable achievements of Pauling&#8217;s hybridization model is that it correctly accounts for the dipole moment of water<\/strong>. If water were perfectly &#8220;linear&#8221;, as many of us might have naively assumed before we learned any chemistry,\u00a0 the dipoles would cancel each other out.<\/p>\n<p>Another example of &#8220;bent&#8221; geometry is found in the amide anion NH<sub>2<\/sub><sup>\u2013<\/sup> which has two lone pairs on nitrogen.<\/p>\n<p>A quick table might help to summarize everything we&#8217;ve established about <em>sp<\/em><sup>3<\/sup> hybridization:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-13991\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/9-summary-of-sp3-hybridization-table-orbital-geometry-and-molecular-geometry.gif\" alt=\"summary-of-sp3-hybridization-table-orbital-geometry-and-molecular-geometry\" width=\"595\" height=\"241\" \/><\/p>\n<h2><strong><a id=\"six\"><\/a>6. sp<sup>2<\/sup>\u00a0Hybridization<\/strong><\/h2>\n<p>Let&#8217;s go back to our pop-bottle analogy. Say we only mix our Sprite with two bottles of Pepsi, not three.<\/p>\n<p>What does that leave us with?<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-13992\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/10-sp2-hybridization-analogy-with-sprite-and-pepsi-bottles-gives-three-hybrid-orbitals-and-one-unhybridized-orbital.gif\" alt=\"sp2-hybridization-analogy-with-sprite-and-pepsi-bottles-gives-three-hybrid-orbitals-and-one-unhybridized-orbital\" width=\"605\" height=\"378\" \/><\/p>\n<p>This gives us <strong>three<\/strong> hybrid bottles of pop, and <b>one<\/b>\u00a0leftover\u00a0<strong>unhybridized <\/strong>bottle.<\/p>\n<p>By analogy,\u00a0\u00a0if we mix the 2s orbital with two 2p orbitals, we obtain <strong>three<\/strong> <em>sp<\/em><sup>2<\/sup> hybrid orbitals, with <strong>one <\/strong>unhybridized p-orbital left over.<\/p>\n<p>When these three <em>sp<\/em><sup>2<\/sup> orbitals are filled with electron pairs, the bond angle that maximizes their distance apart is 120\u00b0.<\/p>\n<p>This gives us a &#8220;trigonal planar&#8221; arrangement of <em>sp<\/em><sup>2<\/sup>\u00a0orbitals, with the unhybridized p orbital at right angles to the plane.\u00a0It kind of resembles a Mercedes Benz symbol.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-13993\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/11-sp2-orbital-hybridization-about-a-central-carbon-atom-three-sp2-orbitals-arranged-120-degrees-and-unhybridized-p-orbital-at-right-angles-to-plane.gif\" alt=\"sp2-hybridization-analogy-with-sprite-and-pepsi-bottles-gives-three-hybrid-orbitals-and-one-unhybridized-orbital\" width=\"505\" height=\"167\" \/><\/p>\n<p>A classic example of this trigonal planar geometry is seen in borane, BH<sub>3\u00a0<\/sub>, which has three pairs of bonding electrons arranged at 120\u00b0 to each other.\u00a0 The trigonal planar geometry is also found in carbocations, such as the methyl cation, CH<sub>3<\/sub><sup>+\u00a0<\/sup>.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-13994\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/12-trigonal-planar-molecules-with-sp2-hybrid-orbitals-borane-bh3-ch3-carbocation.gif\" alt=\"trigonal-planar-molecules-with-sp2-hybrid-orbitals-borane-bh3-ch3-carbocation\" width=\"525\" height=\"189\" \/><\/p>\n<p>You might wonder: where\u00a0 is the unhybridized p orbital?<\/p>\n<p><em>At right angles to the plane. <\/em>Recall that each of the three p orbitals are at right angles to each other. So whichever two p-orbitals hybridize, the third (leftover) p orbital will be at right angles to the plane that they form <em>(just like the z axis is perpendicular to the xy plane)<\/em><\/p>\n<p>In the case of BH<sub>3<\/sub> and carbocations, <strong>the unhybridized p-orbital is empty.<\/strong><\/p>\n<p>There is another very common situation where <em>sp<\/em><sup>2<\/sup> geometry is observed, however. If adjacent atoms have single electrons in unhybridized p-orbitals, and if those p-orbitals can overlap, a bond can result. This is a phenomenon known as &#8220;<strong>pi-bonding<\/strong>&#8220;.\u00a0 (We&#8217;ll have a lot more to say about it later.)<\/p>\n<p>Pi bonds &#8211; which are often just called, &#8220;double bonds&#8221; &#8211; require an unhybridized p orbital in order to form.<\/p>\n<p>The carbon, oxygen, and nitrogen atoms in the examples below, which all have pi bonds (double bonds) are <em>sp<\/em><sup>2<\/sup> hybridized. The orbitals are separated by angles of approximately 120\u00b0.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-13995\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/13-sp2-hybridization-also-present-in-molecules-with-pi-bonds-such-as-ethene-aldehyde-imine.gif\" alt=\"sp2-hybridization-also-present-in-molecules-with-pi-bonds-such-as-ethene-aldehyde-imine\" width=\"485\" height=\"249\" \/><\/p>\n<p>Note that lone pairs can be in <em>sp<\/em><sup>2<\/sup>-hybridized orbitals, just as we saw in NH<sub>3<\/sub> and H<sub>2<\/sub>O in the case of <em>sp<\/em><sup>3<\/sup> hybridization. Also note that in the midde molecule (formaldehyde), the oxygen has two lone pairs (each in <em>sp<\/em><sup>2<\/sup> hybridized orbitals) and in the top right molecule the nitrogen has a single lone pair in a <em>sp<\/em><sup>2<\/sup> hybridized orbital.<\/p>\n<p>When a lone pair is present, the bond angles will be slightly less than 120\u00b0 since the lone pair can be thought of taking up more &#8220;room&#8221;.<\/p>\n<h2><strong><a id=\"seven\"><\/a>7. sp\u00a0Hybridization<\/strong><\/h2>\n<p>Let&#8217;s examine the last possible case. <strong>What if only one p orbital hybridizes with the s orbital? <\/strong><\/p>\n<p>This gives us two hybrid &#8220;<em>sp<\/em>&#8221; orbitals separated by the maximum angle apart: 180 degrees. We call this arrangement, &#8220;linear&#8221;. Each hybrid sp orbital has 50% s character and 50% p character.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-13996\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/14-analogy-of-sprite-and-coke-bottles-with-sp-hybridization-two-hybrid-sp-orbitals-and-two-unhybridized-orbitals.gif\" alt=\"analogy-of-sprite-and-coke-bottles-with-sp-hybridization-two-hybrid-sp-orbitals-and-two-unhybridized-orbitals\" width=\"700\" height=\"521\" \/><\/p>\n<p>The two unhybridized p-orbitals are each at right angles to the <em>sp<\/em> hybrid orbitals.<\/p>\n<p>For instance, here&#8217;s what the orbitals look like in beryllium chloride (BeCl<sub>2<\/sub>) where the\u00a0\u00a0Cl-Be-Cl bond angle is 180\u00b0. If we consider the Cl-Be-Cl bond to be along the x-axis, the two (unhybridized) p-orbitals will be along the y and z axes, respectively.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-13997\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/15-diagram-of-sp-orbital-hybridization-about-a-central-atom-such-as-in-becl2.gif\" alt=\"diagram-of-sp-orbital-hybridization-about-a-central-atom-such-as-in-becl2\" width=\"495\" height=\"194\" \/><\/p>\n<p><em>sp<\/em>-hybridization is more commonly observed in situations where there are <strong>two<\/strong> <strong>pi bonds on a single atom<\/strong>. The most prominent examples are &#8220;triple bonds&#8221;,\u00a0 as seen in alkynes, nitriles, and carbon monoxide (CO). In these cases, not only are the carbon atoms <em>sp<\/em>-hybridized, but so are the nitrogen (in nitriles) and oxygen (in carbon monoxide) atoms.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-13998\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/16-prominent-examples-of-sp-hybridization-are-alkynes-nitriles-carbon-monoxide.gif\" alt=\"prominent-examples-of-sp-hybridization-are-alkynes-nitriles-carbon-monoxide\" width=\"480\" height=\"166\" \/><\/p>\n<p>Note also that lone pairs can be in <em>sp<\/em>-hybridized orbitals, as seen in nitriles and carbon monoxide.<\/p>\n<p><em>sp<\/em>-hybridization is not exclusive to triple bonded atoms &#8211; for example, the central carbons in allene and ketene\u00a0participate in two pi bonds and are therefore <em>sp<\/em>-hybridized &#8211; but triple bonds are the most immediately recognizable examples.<\/p>\n<h2><strong><a id=\"eight\"><\/a>8. Summary &#8211; Hybrid Orbitals<\/strong><\/h2>\n<p>OK. Here are the main points of this unintentionally very long post:<\/p>\n<ul>\n<li>Electron pairs repel. In the absence of orbital hybridization, the bond angles around CH<sub>4<\/sub> would be confined to the geometry of the p-orbitals (90\u00b0).\u00a0 It&#8217;s energetically favorable for the s and p orbitals to <strong>hybridize<\/strong> to form <em>sp<\/em><sup>3<\/sup>\u00a0orbitals which results in a greater separation of the electron pairs and bond angles of 109\u00b0 <em>(i.e. at the apices of a tetrahedron).\u00a0\u00a0<\/em>This also holds for central atoms with non-bonding electron pairs such as NH<sub>3<\/sub> and H<sub>2<\/sub>O.<\/li>\n<li>When only two p orbitals participate in hybridization, three <em>sp<\/em><sup>2\u00a0<\/sup> hybrid orbitals result that adopt a trigonal planar orbital geometry. The remaining (unhybridized) p orbital, which is at right angles to the trigonal plane,\u00a0 can either be empty (as in BH<sub>3<\/sub>) or singly-occupied (as seen in molecules containing pi bonds).<\/li>\n<li>When only one p orbital participates in hybridization, the result is two <em>sp<\/em> hybrid orbitals and a linear orbital geometry. The two remaining p orbitals are available for pi-bonding (as in triply-bonded organic compounds such as alkynes and nitriles) or can be empty (as in BeCl<sub>2<\/sub>).<\/li>\n<li>Note that the number of orbitals around the central atom is <strong>always<\/strong> 4. Orbitals are neither created nor destroyed by hybridization; they are merely transformed.<\/li>\n<\/ul>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-13999\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/11\/17-summary-of-hybrid-orbitals-sp3-sp2-and-sp-relationship-between-molecular-geometry-and-orbital-geometry.gif\" alt=\"summary-of-hybrid-orbitals-sp3-sp2-and-sp-relationship-between-molecular-geometry-and-orbital-geometry\" width=\"641\" height=\"267\" \/><\/p>\n<p>In the next post we will just provide a super simple trick for quickly determining the hybridization of a central atom.<\/p>\n<p><em><strong>Thanks again to Matt for co-authoring. Ask Matt about scheduling an online tutoring session\u00a0<a href=\"https:\/\/masterorganic.wufoo.com\/forms\/q1yg3qx8076h7gx\/\">here<\/a>. <\/strong><\/em><\/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\/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\/2017\/06\/07\/valence-electrons\/\" class=\"\"><span>Valence Electrons of the First Row Elements<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/09\/24\/how-to-calculate-formal-charge\/\" class=\"\"><span>A Key Skill: How to Calculate Formal Charge<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/11\/23\/introduction-to-resonance\/\" class=\"\"><span>Introduction to Resonance<\/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\/2011\/12\/22\/in-summary-resonance\/\" class=\"\"><span>In Summary: Evaluating Resonance Structures<\/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><li><a href=\"https:\/\/www.masterorganicchemistry.com\/organic-chemistry-practice-problems\/structure-and-bonding-practice-quizzes\/\" class=\"\"><span>Structure and Bonding Practice Quizzes (MOC Membership)<\/span><\/a><\/li><\/ul><\/div>\n<hr 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Here&#8217;s a quick summary: [Note: This\u00a0post was co-authored with Matthew Pierce of\u00a0Organic Chemistry Solutions.\u00a0 Ask Matt about scheduling <\/p>\n","protected":false},"author":1,"featured_media":13982,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1406],"tags":[183,399,237,1280,746,745,615,678,679],"post_folder":[],"class_list":["post-11040","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-bonding-structure-resonance","tag-bonding","tag-hybridization","tag-molecular-geometry","tag-orbital-geometry","tag-p-orbitals","tag-s-orbitals","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>What Are Hybrid Orbitals and Hybridization? &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"What are hybrid orbitals? 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