{"id":10565,"date":"2017-02-28T16:15:42","date_gmt":"2017-02-28T22:15:42","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=10565"},"modified":"2026-05-07T05:48:31","modified_gmt":"2026-05-07T10:48:31","slug":"pi-molecular-orbitals-of-butadiene","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2017\/02\/28\/pi-molecular-orbitals-of-butadiene\/","title":{"rendered":"Pi Molecular Orbitals of Butadiene"},"content":{"rendered":"<p><strong>The Molecular Orbital Diagram of Butadiene, And How To Build It<\/strong><\/p>\n<ul>\n<li>Butadiene is a\u00a0<strong>conjugated\u00a0<\/strong>diene consisting of two adjacent pi-bonds and comprised of 4 p-orbitals and 4 pi-electrons.<\/li>\n<li>To draw the molecular orbital diagram of butadiene, start by drawing 4 p-orbitals all aligned with the same phase. This has <strong>zero<\/strong> nodes and is the\u00a0<strong>lowest energy pi-orbital\u00a0<\/strong>(\u03c0<sub>1<\/sub> )<\/li>\n<li>As the number of\u00a0<strong>nodes<\/strong> in an orbital increases, so does its energy. The highest-energy molecular orbital has\u00a0<strong>three\u00a0<\/strong>nodes and has all p-orbitals with opposite\u00a0 phases (\u03c0<sub>4<\/sub>)<\/li>\n<li>Intermediate orbitals (\u03c0<sub>2\u00a0<\/sub>) and\u00a0 (\u03c0<sub>3<\/sub> ) have one and two nodes, respectively.<\/li>\n<li>Once the molecular orbital diagram is built, the next step is to add the 4\u00a0 <strong>pi-electrons<\/strong>. This will fill up the lowest-energy orbital <strong>\u00a0<\/strong>(\u03c0<sub>1<\/sub> ) and the second-lowest-energy orbital\u00a0<strong>\u00a0<\/strong>(\u03c0<sub>2<\/sub> )<\/li>\n<li>The\u00a0<strong>highest-occupied\u00a0<\/strong>molecular orbital (HOMO) of butadiene is the highest-energy orbital that contains pi-electrons. This is\u00a0 \u03c0<sub>2<\/sub><\/li>\n<li>The\u00a0<strong>lowest-unoccupied\u00a0<\/strong>molecular orbital (LUMO) of butadiene is the lowest-energy orbital that has\u00a0<strong>zero <\/strong>pi-electrons. This is\u00a0\u03c0<sub>3<\/sub><\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-33863\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/0-summary-of-the-pi-molecular-orbitals-of-butadiene.gif\" alt=\"summary of the pi molecular orbitals of butadiene\" width=\"640\" height=\"598\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li class=\"p1\"><a href=\"#one\"><span class=\"s1\"><span class=\"s1\">Helpful Hints On Drawing The Pi Molecular Orbitals Of A Conjugated System: A Quick Review<\/span><\/span><\/a><\/li>\n<li class=\"p1\"><a href=\"#two\">The Butadienyl Pi System (n = 4)<\/a><\/li>\n<li class=\"p1\"><a href=\"#three\"><span class=\"s1\">The Lowest-Energy Molecular Orbital (\u03c0<\/span><span class=\"s2\"><sub>1<\/sub><\/span><span class=\"s1\"><span class=\"s1\">) Of The Butadiene Pi System Has Zero Nodes<\/span><\/span><\/a><\/li>\n<li class=\"p1\"><a href=\"#four\">The Highest-Energy Molecular Orbital (\u03c0<span class=\"s2\"><sub>4<\/sub><\/span><span class=\"s1\"><span class=\"s1\">) Has Three Nodes<\/span><\/span><\/a><\/li>\n<li class=\"p1\"><a href=\"#five\">The Second-Lowest-Energy Molecular Orbital (\u03c0<span class=\"s2\"><sub>2<\/sub><\/span><span class=\"s1\"><span class=\"s1\">) Has One Node<\/span><\/span><\/a><\/li>\n<li class=\"p1\"><a href=\"#six\">The Third-Lowest-Energy Molecular Orbital (\u03c0<span class=\"s2\"><sub>3<\/sub><\/span><span class=\"s1\"><span class=\"s1\">) Has Two Nodes<\/span><\/span><\/a><\/li>\n<li class=\"p1\"><a href=\"#seven\">The Full Molecular Orbital Diagram For The Butadienyl System (n=4)<\/a><\/li>\n<li class=\"p1\"><a href=\"#eight\">\u00a0Populating The Molecular Orbitals Of Butadiene With Electrons<\/a><\/li>\n<li class=\"p1\"><a href=\"#nine\">Identifying The &#8220;HOMO&#8221; And &#8220;LUMO&#8221; Of Butadiene<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quizzes\">Quiz Yourself!<\/a><\/li>\n<li><a href=\"#references\">(Advanced) References and Further Reading<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><strong><a id=\"one\"><\/a>1. Drawing The Pi Molecular Orbitals Of A Conjugated System: A Quick Review<\/strong><\/h2>\n<p>In the last post in this series we<a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/02\/16\/molecular-orbitals-of-the-allyl-cation-allyl-radical-and-allyl-anion\/\"> built up the pi molecular orbitals of the allyl pi-system<\/a>, consisting of three consecutive p orbitals in conjugation. In this article we will show how to build the pi molecular orbital diagram of butadiene.<\/p>\n<p>In the last post, we saw that:<\/p>\n<ul>\n<li><strong>The number of molecular orbitals (n) for a pi-system is equal to the number of contributing <em>p<\/em> orbitals.<\/strong> For the allyl system, n=3. We had three contributing <em>p<\/em> orbitals and thus three pi\u00a0molecular orbitals.<\/li>\n<li><strong>The lowest-energy orbital always has zero nodes between the <em>p<\/em>-orbitals\u00a0<\/strong><em><span style=\"color: #993366;\">(note that we say &#8220;no nodes between the p-orbitals&#8221; because we&#8217;re not counting the node between the individual lobes, which is inherent to\u00a0all\u00a0p-orbitals).<\/span>\u00a0<\/em>That is, in the lowest-energy orbital, all phases of the contributing<em> p<\/em>-orbitals are aligned the same way. \u00a0<em><br \/>\n<img decoding=\"async\" class=\"alignnone wp-image-15581\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-review-of-molecular-orbitals-of-allyl-system-lowest-energy-molecular-orbital-has-zero-nodes-between-orbitals-all-are-completely-aligned.gif\" alt=\"review of molecular orbitals of allyl system lowest energy molecular orbital has zero nodes between orbitals all are completely aligned\" width=\"450\" height=\"108\" \/><br \/>\n<\/em><\/li>\n<li><strong>The number of nodes between<em> p<\/em>-orbitals increases by 1 for each successive energy level<\/strong>, such that\u00a0the highest-energy orbital has (n-1) nodes (all phases of contributing <em>p<\/em>-orbitals alternate).<br \/>\n<img decoding=\"async\" class=\"alignnone wp-image-15582\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-review-highest-energy-molecular-orbital-of-allyl-system-two-nodes-all-p-orbitals-alternate-nodes-between-orbitals.gif\" alt=\"review highest energy molecular orbital of allyl system two nodes all p orbitals alternate nodes between orbitals\" width=\"450\" height=\"98\" \/><\/li>\n<li><strong>The lowest and highest energy orbitals are always the easiest pi molecular orbitals to draw.<\/strong> It&#8217;s helpful to draw them first.<\/li>\n<li><strong>The trick to drawing the\u00a0orbital(s) of intermediate energy is to understand where to put the node(s)<\/strong>. Nodes are positioned in a way such that they are\u00a0<em>symmetrical<\/em> relative to the centre. A system with 1 node has the node smack in the centre (right on the central atom, in fact). A system with 2 nodes will have the nodes at equal distance relative to the centre.<\/li>\n<li><strong>It&#8217;s helpful to draw out all the orbitals of the pi system first, and <em>then<\/em> add the pi-electrons to it.<\/strong><\/li>\n<\/ul>\n<p>Today&#8217;s\u00a0post actually doesn&#8217;t introduce any new concepts. We&#8217;re just going to take everything from the previous post on building up the orbitals of the allyl system (n=3) and apply it towards drawing the orbitals of the butadienyl system (n=4).<\/p>\n<p>We&#8217;ll gain a full appreciation of the importance of the molecular orbitals for butadiene\u00a0in\u00a0a little while\u00a0when we start exploring a curious little reaction discovered by<a href=\"https:\/\/en.wikipedia.org\/wiki\/Diels\u2013Alder_reaction\"> Otto Diels and Kurt Alder back in 1928.<\/a><\/p>\n<h2><a id=\"two\"><\/a>2. The Butadienyl Pi System (n = 4)<\/h2>\n<p>As the name suggests, butadiene is composed of 4 carbons with two adjacent pi bonds. \u00a0 As we showed in this earlier post on conjugation and resonance, these two pi bonds are <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/01\/24\/conjugation-and-resonance\/\">conjugated<\/a>\u00a0: all four\u00a0p orbitals are all aligned with each other, and build up into a larger pi system. It&#8217;s for this reason that we can describe the electron density in butadiene with resonance forms, which show alternative distributions of pi electrons in the molecule.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15583\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-review-of-butadiene-with-minor-resonance-form-butadiene-has-4-conjugated-p-orbitals.gif\" alt=\"review of butadiene with minor resonance form butadiene has 4 conjugated p orbitals\" width=\"600\" height=\"137\" \/><\/p>\n<p>Since butadiene consists of 4 individual p orbitals, the pi-system of butadiene will contain 4 pi <strong>molecular orbitals<\/strong>.<\/p>\n<p>Using the principles we learned from drawing out the pi molecular orbitals of the allyl system, let&#8217;s try to draw out what each of these four molecular orbitals should look like.<\/p>\n<h2><strong><a id=\"three\"><\/a>3. The Lowest-Energy Molecular Orbital (\u03c0<sub>1<\/sub>) Of The Butadiene Pi System Has Zero Nodes<\/strong><\/h2>\n<p>The lowest energy molecular orbital will have p orbitals with phases in complete alignment with each other. This is very easy to draw: just draw four consecutive p-orbitals with their lobes aligned the same way.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15584\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-since-butadiene-has-4-p-orbitals-butadiene-will-have-4-pi-molecular-orbitals-lowest-energy-orbital-will-have-zero-nodes-all-p-orbitals-aligned.gif\" alt=\"since butadiene has 4 p orbitals butadiene will have 4 pi molecular orbitals lowest energy orbital will have zero nodes all p orbitals aligned\" width=\"630\" height=\"213\" \/><\/p>\n<p>We could have also drawn the pi-system with all the shaded lobes pointing up: it&#8217;s the same thing. The constructive overlap between the lobes results in a pi orbital that extends over the entire length of the pi system (above right); there are zero nodes between the p orbitals themselves. A physical interpretation of this orbital is that an electron in this orbital is delocalized over the length of the pi system. [<a href=\"#notetwo\">Note 2<\/a>]<\/p>\n<h2><strong><a id=\"four\"><\/a>4. The <\/strong><b>Highest-Energy Molecular Orbital (<strong>\u03c0<sub>4<\/sub>) Has Three Nodes<\/strong><\/b><\/h2>\n<p>The highest-energy molecular orbital is also very easy to draw. Just draw n (4 in our case) p orbitals and alternate the phases of each.\u00a0\u00a0This creates a pi system with\u00a0three\u00a0nodes (areas where the lobes change sign). We&#8217;ve drawn the nodes in as red dotted lines.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15585\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-butadiene-system-has-four-pi-molecular-orbitals-highest-energy-molecular-orbital-will-have-all-alternating-p-orbitals-three-nodes-most-unstable.gif\" alt=\"butadiene system has four pi molecular orbitals highest energy molecular orbital will have all alternating p orbitals three nodes most unstable\" width=\"600\" height=\"181\" \/><\/p>\n<h2><strong><a id=\"five\"><\/a>5. The Second-Lowest-Energy Molecular Orbital <b>(\u03c0<sub><span style=\"font-size: small;\"><span style=\"line-height: 20px;\">2<\/span><\/span><\/sub>) Has One Node<\/b><\/strong><\/h2>\n<p>The second-lowest-energy molecular orbital in butadiene will have 1 node. The trick is knowing where to put it.<\/p>\n<p>As we saw with the allyl system, the node cannot just be placed anywhere; the mathematical properties of the Schr\u00f6dinger wave equation (which we don&#8217;t need to get into) dictate its position. Thankfully, node placement for this orbital is pretty straightforward: just plunk it in the middle.<em>(This goes for all systems with a single node, by the way).\u00a0<\/em><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15586\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-the-second-molecular-orbital-of-butadiene-pi-system-has-one-node-in-the-center-of-the-pi-system-between-c2-and-c3.gif\" alt=\"the second molecular orbital of butadiene pi system has one node in the center of the pi system between c2 and c3\" width=\"600\" height=\"240\" \/><\/p>\n<p>Note how the phases flip in the centre of the pi orbital. This corresponds to the situation we&#8217;d expect to see for two adjacent non-interacting pi bonds, where the electrons are each confined to pi orbitals spanning two carbons each, with a node in the middle (above right).<\/p>\n<h2><strong><a id=\"six\"><\/a>6. The Third-Lowest-Energy Molecular Orbital <b>(\u03c0<sub>3<\/sub>) Has Two Nodes<\/b><\/strong><\/h2>\n<p>Finally we come to the third-lowest-energy molecular orbital (or second-highest, if you prefer).\u00a0This has two nodes.<\/p>\n<p>Where to place them?<\/p>\n<p>The general principle is that they are placed <strong>symmetrically<\/strong> with respect to the centre. \u00a0This is what the orbital picture looks like: [<a href=\"#notetwo\">Note 2<\/a>]<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15587\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-the-third-molecular-orbital-in-the-pi-system-of-butadiene-has-two-nodes-between-c1-and-c2-and-c3-and-c4-pi-3.gif\" alt=\"the third molecular orbital in the pi system of butadiene has two nodes between c1 and c2 and c3 and c4 pi 3\" width=\"600\" height=\"240\" \/><\/p>\n<p>This gives us a 2-carbon pi orbital in the centre flanked by two one-carbon orbitals on the sides.<\/p>\n<h2><strong><a id=\"seven\"><\/a>7. The Full Molecular Orbital Diagram For The <\/strong><b>Butadienyl System (n=4)\u00a0<\/b><\/h2>\n<p>Now that we have all the pieces, all we need to do to construct the molecular orbital diagram for the butadienyl system is to arrange the orbitals in order of increasing energy. That gives us the following figure (note that we haven&#8217;t added any electrons to it yet).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15588\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/8-full-pi-molecular-orbital-diagram-for-butadiene-showing-lowest-number-of-nodes-at-bottom-and-highest-at-top-no-electrons-just-yet-pi-1-pi-2-pi-3-pi-4.gif\" alt=\"full pi molecular orbital diagram for butadiene showing lowest number of nodes at bottom and highest at top no electrons just yet pi 1 pi 2 pi 3 pi 4\" width=\"600\" height=\"581\" \/><\/p>\n<p>A molecular orbital diagram without electrons is like an apartment building without people. So let&#8217;s pick the simplest possible molecule to apply to this system: butadiene.<\/p>\n<h2><a id=\"eight\"><\/a>8. Populating The Molecular Orbitals Of Butadiene With Electrons<\/h2>\n<p>Butadiene has two double bonds with two electrons each, for a total of 4 pi electrons. We fill up the lowest-energy molecular orbitals first, which gives us the following:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15589\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/9-full-molecular-orbital-diagram-for-butadiene-showing-electrons-and-that-homo-is-pi-2-and-lumo-is-pi-3.gif\" alt=\"full molecular orbital diagram for butadiene showing electrons and that homo is pi 2 and lumo is pi 3\" width=\"600\" height=\"559\" \/><\/p>\n<p>We&#8217;ve highlighted two molecular orbitals on this diagram as being of particular interest, because, as we&#8217;ll see, they&#8217;re where the action usually happens. The are sometimes called the &#8220;frontier&#8221; orbitals.<\/p>\n<h2><a id=\"nine\"><\/a>9. Identifying The &#8220;HOMO&#8221; And &#8220;LUMO&#8221; Of Butadiene<\/h2>\n<p>The\u00a0<strong>highest occupied molecular orbital\u00a0<\/strong>(HOMO) is \u03c02.\u00a0You can think of the HOMO as being a little bit like the &#8220;valence electrons&#8221; of the pi system: they&#8217;re the most readily lost. If butadiene participates in a reaction where it is the electron-donor (nucleophile), its electrons are going to come from that orbital.<\/p>\n<p>The <strong>lowest-unoccupied molecular orbital<\/strong> (LUMO) is \u03c03.\u00a0The LUMO is the lowest-energy unoccupied orbital. If butadiene participates in a reaction where it is the electron acceptor (electrophile), the electrons will be donated to that orbital.<\/p>\n<p>We&#8217;ll have more to say about the HOMO and LUMO shortly, but that&#8217;s sufficient for now.<\/p>\n<p>Now here&#8217;s a quiz for you, based on what we&#8217;ve gone through today:<\/p>\n<ul>\n<li>How would you draw the molecular orbital diagram for the pentadienyl cation\u00a0(n = 5) ?<\/li>\n<li>Can you draw the MO diagram of the butadienyl radical anion?<\/li>\n<\/ul>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-25516\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2017\/02\/10-quiz-can-you-draw-the-molecular-orbital-diagram-for-the-butadienyl-radical-anion.gif\" alt=\"quiz can you draw the molecular orbital diagram for the butadienyl radical anion\" width=\"600\" height=\"183\" \/><\/a><\/p>\n<p>Answers below. [<a href=\"#notethree\">Note 3<\/a>]<\/p>\n<p><em>Thanks to\u00a0Thomas Struble\u00a0for assistance\u00a0with this post.<\/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\/2017\/03\/22\/reactions-of-dienes-12-and-14-addition\/\" class=\"\"><span>Reactions of Dienes: 1,2 and 1,4 Addition<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/02\/16\/molecular-orbitals-of-the-allyl-cation-allyl-radical-and-allyl-anion\/\" class=\"\"><span>Molecular Orbitals of The Allyl Cation, Allyl Radical, and Allyl Anion<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/02\/14\/molecular-orbital-pi-bond\/\" class=\"\"><span>Bonding And Antibonding Pi Orbitals<\/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\/2016\/09\/08\/conjugation_and_color\/\" class=\"\"><span>Conjugation And Color (+ How Bleach Works)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/09\/16\/introduction-to-uv-vis-spectroscopy\/\" class=\"\"><span>Introduction To UV-Vis Spectroscopy<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/08\/30\/the-diels-alder-reaction\/\" class=\"\"><span>The Diels-Alder Reaction<\/span><\/a><\/li><\/ul><\/div>\n<p><a id=\"noteone\"><\/a><strong>Note 1. <\/strong>\u00a0I don&#8217;t want to get into <a href=\"https:\/\/en.wikipedia.org\/wiki\/Particle_in_a_box\">Particle In A Box<\/a>, but if you look at electrons as waves and think about their energies according to E = h\u03bd , the longer the &#8220;box&#8221; an electron is confined to, the lower its energy will be. This is a quick argument as to why delocalization of electrons is energetically favourable.<\/p>\n<p><a id=\"notetwo\"><\/a><strong>Note 2. <\/strong>Not going to touch the <a href=\"https:\/\/en.wikipedia.org\/wiki\/H\u00fcckel_method\">H\u00fcckel treatment<\/a> of molecular orbitals here. Fleming, &#8220;<a href=\"https:\/\/www.amazon.com\/Frontier-Orbitals-Organic-Chemical-Reactions\/dp\/0471018198\">Frontier Orbitals and Organic Chemical Reactions<\/a>&#8221; is the place to go if you&#8217;re curious for a rigorous yet practical treatment of molecular orbital theory.<\/p>\n<p><strong><a id=\"notethree\"><\/a>Note 3. Answers. <\/strong>Pentadienyl cation:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15591\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F1-molecular-orbital-diagram-for-a-five-p-oribtal-system-pentadienyl-cation-four-electrons-showing-homo-and-lumo-for-the-system.gif\" alt=\"molecular orbital diagram for a five p oribtal system pentadienyl cation four electrons showing homo and lumo for the system\" width=\"630\" height=\"642\" \/><\/p>\n<p>Butadienyl radical anion: just take our MO diagram for butadiene, and put an electron in\u00a0\u03c03 (i.e. the LUMO of butadiene). It&#8217;s really that simple.<\/p>\n<hr \/>\n<h2><a id=\"quizzes\"><\/a>Quiz Yourself!<\/h2>\n<p><br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0062-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0065-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0334-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0348-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0074-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3320-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<hr \/>\n<h2><a id=\"references\"><\/a>(Advanced) References and Further Reading<\/h2>\n<p>Structure of butadiene using calculations from <a href=\"https:\/\/www.rowansci.com\/\">Rowan<\/a>:<\/p>\n<p>C1-C2 (pi) bond length: 1.319 \u00c5<br \/>\nC2-C3 (sigma) bond length: 1.489 \u00c5 (normal C-C bond length: 1.51 \u00c5 )<\/p>\n<p><iframe title=\"Structure of Butadiene\" src=\"https:\/\/labs.rowansci.com\/iframe\/calculations\/b8b8d481-52dc-4b1e-a37d-868373380b18\" width=\"640\" height=\"640\"><\/iframe><\/p>\n<p>Butadiene molecular orbital calculations from <a href=\"https:\/\/rowansci.com\/\">Rowan<\/a>:<\/p>\n<p><iframe title=\"Butadiene molecular orbitals\" src=\"https:\/\/labs.rowansci.com\/iframe\/calculations\/1efe316b-825e-4fee-956c-3803a5e2604c\" width=\"640\" height=\"640\"><\/iframe><\/p>\n","protected":false},"excerpt":{"rendered":"<p>The Molecular Orbital Diagram of Butadiene, And How To Build It Butadiene is a\u00a0conjugated\u00a0diene consisting of two adjacent pi-bonds and comprised of 4 p-orbitals and <\/p>\n","protected":false},"author":1,"featured_media":33863,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1163],"tags":[1187,1188,940,941,612],"post_folder":[],"class_list":["post-10565","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-dienes-and-mo-theory","tag-butadiene","tag-frontier-orbitals","tag-homo","tag-lumo","tag-molecular-orbitals"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>The Pi Molecular Orbitals of Butadiene And How To Draw Them<\/title>\n<meta name=\"description\" content=\"The molecular orbital diagram of butadiene, and a system for drawing all of its pi molecular orbitals, and determining the HOMO and LUMO.\" \/>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, 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