{"id":12032,"date":"2018-11-05T06:00:53","date_gmt":"2018-11-05T11:00:53","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=12032"},"modified":"2025-11-10T19:28:26","modified_gmt":"2025-11-11T01:28:26","slug":"regiochemistry-in-the-diels-alder-reaction","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2018\/11\/05\/regiochemistry-in-the-diels-alder-reaction\/","title":{"rendered":"Regiochemistry In The Diels-Alder Reaction"},"content":{"rendered":"<p><strong>Regiochemistry (&#8220;Regioselectivity&#8221;) In The Diels-Alder Reaction<\/strong><\/p>\n<p>The Diels-Alder is an onion, and we just keep peeling back the layers.<\/p>\n<ul>\n<li>When <strong>non-symmetrical dienes<\/strong> react with <strong>non-symmetrical dienophiles<\/strong>, two <strong>regioisomers<\/strong> (constitutional isomers) are possible.<\/li>\n<li>Dienes with substituents on the <strong>terminus<\/strong> (&#8220;1-substituted dienes&#8221;) tend to give &#8220;<strong>1,2<\/strong>&#8221; products (<span style=\"color: #993366;\"><em>nicknamed &#8220;ortho&#8221;<\/em><\/span>).<\/li>\n<li>Dienes with substituents on the <strong>2-position<\/strong> (&#8220;2-substituted dienes&#8221;) tend to give the &#8220;<strong>1,4<\/strong>&#8221; product (<span style=\"color: #993366;\"><em>nicknamed &#8220;para&#8221;<\/em><\/span>).<\/li>\n<li>In general, &#8220;1,3&#8221; products (&#8220;meta&#8221;) are only <strong>minor<\/strong> byproducts.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-15729\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/0-summary-of-regiocheistry-in-the-diels-alder-reaction-ortho-and-para-products-are-favored-not-meta.gif\" alt=\"summary of regiocheistry in the diels alder reaction ortho and para products are favored not meta\" width=\"600\" height=\"605\" \/><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Regiochemistry In The Diels-Alder Reaction<\/a><\/li>\n<li><a href=\"#two\">Flashback: Markovnikov&#8217;s Rule and &#8220;Regioselectivity&#8221;<\/a><\/li>\n<li><a href=\"#three\">The Diels-Alder Reaction Is Regioselective<\/a><\/li>\n<li><a href=\"#four\">Summary: Regioselectivity In The Diels-Alder Reaction<\/a><\/li>\n<li><a href=\"#notes\">Notes (more on the origin of regioselectivity)<\/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. &#8220;Regiochemistry&#8221; In The Diels-Alder Reaction<\/strong><\/h2>\n<p>So far in the Diels-Alder, we&#8217;ve seen examples of:<\/p>\n<ul>\n<li>symmetrical dienes with symmetrical dienophiles<\/li>\n<li>unsymmetrical dienes with symmetrical dienophiles<\/li>\n<li>symmetrical dienes with unsymmetrical dienophiles<\/li>\n<\/ul>\n<p>These three situations (laid out in the image below) each have the potential to form <strong>stereoisomers<\/strong> (i.e. diastereomers and\/or enantiomers). But all the products have exactly the same <strong>connectivity<\/strong>.<\/p>\n<p>This brings us to a particularly challenging case. What happens when we have an\u00a0<em>unsymmetrical\u00a0<\/em>diene reacting with an\u00a0<em>unsymmetrical\u00a0<\/em>dienophile?<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15730\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-four-cases-of-diels-alder-reaction-unsymmetrical-diene-with-unsymmetrical-dienophile-gives-different-regioisomer-possibilities.gif\" alt=\"four cases of diels alder reaction unsymmetrical diene with unsymmetrical dienophile gives different regioisomer possibilities\" width=\"630\" height=\"406\" \/><\/p>\n<p>Why is this situation different from the first three?<\/p>\n<p><strong>Because there are two different ways for the diene and dienophile to &#8220;line up! &#8220;<\/strong>.\u00a0 In the example above, the diene and dienophile can come together two ways:<\/p>\n<ul>\n<li>&#8220;head to head&#8221; such that the methyl group on the diene and the C=O bond point in the same direction (giving the top product);<\/li>\n<li>&#8220;head to tail&#8221; such that they point in the opposite direction (bottom product).<\/li>\n<\/ul>\n<p>How are these products related to each other, overall (not counting stereochemistry)?<\/p>\n<p>Since they have the same molecular formula but different connectivity,\u00a0\u00a0they&#8217;re <strong>constitutional isomers<\/strong>.<\/p>\n<p>Now comes the big question. In this kind of a Diels-Alder, are these products formed in roughly <em>equal<\/em> ratios&#8230; or\u00a0is there a preference for one type of connectivity over another?<\/p>\n<p>The short answer is, &#8220;<strong>yes, the Diels-Alder has a preference for one type of connectivity.&#8221; <\/strong><\/p>\n<p>In other words, the reaction has regioselectivity.<\/p>\n<p>Wait. What&#8217;s<em> regioselectivity?\u00a0<\/em>Quick review:<\/p>\n<h2><strong><a id=\"two\"><\/a>2. Flashback: Markovnikov&#8217;s Rule and &#8220;Regioselectivity&#8221;<\/strong><\/h2>\n<p>Where have we seen this type of situation before?<\/p>\n<p>With alkenes! We saw that adding an acid like HCl to an alkene like 1-butene, we could obtain two possible products: 1-chlorobutane or 2-chlorobutane. <em>[See: <a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/02\/08\/markovnikovs-rule-1\/\">Markovnikov&#8217;s Rule<\/a>]<\/em><\/p>\n<p>These products have the same molecular formula, but different connectivity, which makes them constitutional isomers.<\/p>\n<p>However, we saw that the reaction doesn&#8217;t give an equal ratio of products. Instead, there&#8217;s about a 4:1 preference for 2-chlorobutane over 1-chlorobutane, which we saw was due to a greater preference for the more stable carbocation intermediate.<\/p>\n<p>This preference goes by the name &#8220;Markovnikov&#8217;s Rule&#8221;:<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15731\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-example-of-regioselectivity-is-markovnikovs-rule-addition-of-hcl-to-alkenes-giving-major-and-minor-products.gif\" alt=\"example of regioselectivity is markovnikovs rule addition of hcl to alkenes giving major and minor products\" width=\"600\" height=\"360\" \/><\/p>\n<p>The tendency of alkenes to obey &#8220;Markovnikov&#8217;s rule&#8221; in these reactions is an example of\u00a0<strong>regioselectivity<\/strong><em>.\u00a0<\/em>The reaction is\u00a0<strong>selective<\/strong>\u00a0in forming one constitutional isomer over another.<\/p>\n<p><span style=\"color: #993366;\"><em>(We say &#8220;selective&#8221; and <strong>not<\/strong> &#8220;specific&#8221; because more than one product is formed.\u00a0Use of the prefix &#8220;regio&#8221; comes from the observation that the chloride tends to attack one region of the double bond, and the proton, another. )<\/em><\/span><\/p>\n<p><span style=\"color: #993366;\"><em>It&#8217;s worth noting that 2-chlorobutane is formed as a racemic mixture of enantiomers. So while the reaction is regioselective, it is\u00a0<span style=\"text-decoration: underline;\">not<\/span> enantioselective.<\/em><\/span><\/p>\n<h2><strong><a id=\"three\"><\/a>3. The Diels Alder Is Regioselective\u00a0<\/strong><\/h2>\n<p>Like the reaction of acids with alkenes, the Diels-Alder reaction is regioselective. Two main cases will illustrate the point.<\/p>\n<h3><strong>Case 1: 1-substituted dienes<\/strong><\/h3>\n<p>The first important case concerns a diene with a substituent on the &#8220;1&#8221; position of the diene, such as 1-methoxybutadiene.<span style=\"color: #993366;\"> <em>(I know that if a methyl group were present instead, it would technically be the &#8220;4&#8221; position according to IUPAC &#8211; bear with me on this).\u00a0<\/em><\/span><\/p>\n<p>Consider the Diels-Alder of 1-methoxy butadiene with methyl methacrylate. There are two ways that the diene and dienophile can connect.<\/p>\n<ul>\n<li>Line it up one way (&#8220;<strong>head to head<\/strong>&#8220;, below), and you get a new six-membered ring where two substituents are on two adjacent carbons (a &#8220;1,2&#8221; relationship)<\/li>\n<li>Line it up another way (&#8220;<strong>head to tail<\/strong>&#8220;), and the two substituents have a &#8220;1,3&#8221; relationship.<\/li>\n<\/ul>\n<p>These two products have different connectivity and are therefore<strong> constitutional isomers<\/strong> (&#8220;regioisomers&#8221;).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15732\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-first-case-for-regiochemistry-in-diels-alder-is-1-substituted-dienes-with-unsymmetrical-dienophiles-1-methoxybutadiene-constitutional-isomers.gif\" alt=\"first case for regiochemistry in diels alder is 1 substituted dienes with unsymmetrical dienophiles 1 methoxybutadiene constitutional isomers\" width=\"600\" height=\"444\" \/><\/p>\n<p>By analogy to aromatic nomenclature,\u00a0the &#8220;1,2&#8221; and &#8220;1,3&#8221;\u00a0 patterns are <strong>nicknamed<\/strong> <em>ortho-<\/em> and <em>meta-<\/em> respectively.<span style=\"color: #993366;\"> <em>[I say &#8220;nicknamed&#8221; because these are terms of convenience, nothing else. Don&#8217;t tell IUPAC!]<\/em><\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15733\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-aromatic-relationships-ortho-meta-para-analogy-to-diels-alder-products.gif\" alt=\"aromatic relationships ortho meta para analogy to diels alder products\" width=\"600\" height=\"246\" \/><\/p>\n<p>So which of the two Diels-Alder products is favored? The &#8220;<em>ortho&#8221;\u00a0<\/em>or the\u00a0<em>&#8220;meta&#8221;\u00a0<\/em>?<\/p>\n<p>Here&#8217;s what&#8217;s experiments tell us:<\/p>\n<p><strong>The <em>ortho<\/em> product is major and the <em>meta\u00a0<\/em>product is minor.<\/strong><\/p>\n<p>This holds for a large number of 1-substituted dienes; I&#8217;ll just show two. <span style=\"color: #993366;\"><em>Hans Reich at UW-Madison has a longer list of examples &#8211; <span style=\"text-decoration: underline;\"><a style=\"color: #993366; text-decoration: underline;\" href=\"https:\/\/www.chem.wisc.edu\/areas\/reich\/chem547\/4-pericyclic%7B04%7D.htm\">see here<\/a>.<\/span><\/em><\/span><\/p>\n<ul>\n<li>With 1-methoxybutadiene, the\u00a0<em>ortho<\/em> is the only product!!<\/li>\n<li>When a methyl group is in that position, the\u00a0<em>ortho<\/em> outnumbers <em>met<\/em><em>a<\/em> by about 8:1<\/li>\n<\/ul>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15734\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-1-substituted-dienes-favor-1-2-ortho-product-not-meta-product-example-of-1-methoxybutadiene-with-methyl-acrylate.gif\" alt=\"1 substituted dienes favor 1 2 ortho product not meta product example of 1 methoxybutadiene with methyl acrylate\" width=\"600\" height=\"412\" \/><\/p>\n<h3><strong>Case 2:\u00a0 2-substituted dienes<\/strong><\/h3>\n<p>The second important case is when there&#8217;s a substituent on the 2-position of the diene, such as 2-methylbutadiene.<\/p>\n<p>Again, there are two ways it can line up, except this time it&#8217;s to provide\u00a0<em>para<\/em> (1,4) and\u00a0<em>meta<\/em> (1,3) products.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15735\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-2-substituted-dienes-with-unsymmetrical-dienophiles-can-give-two-different-regioisomers.gif\" alt=\"2 substituted dienes with unsymmetrical dienophiles can give two different regioisomers\" width=\"600\" height=\"414\" \/><\/p>\n<p>So which of these products is dominant?<\/p>\n<p><strong>The <em>para<\/em> product is major and the <em>meta\u00a0<\/em>product is minor.<\/strong><\/p>\n<ul>\n<li>2-methoxybutadiene favors the\u00a0<em>para<\/em> product by about 8:1<\/li>\n<li>2-methylbutadiene favors the\u00a0<em>para<\/em> product by about 2:1<\/li>\n<\/ul>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15736\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-2-substituted-dienes-favor-1-4-para-product-not-meta-product-example-of-methoxybutadiene-and-methyl-acrylate.gif\" alt=\"2 substituted dienes favor 1 4 para product not meta product example of methoxybutadiene and methyl acrylate\" width=\"630\" height=\"390\" \/><\/p>\n<p>What if there&#8217;s substituents on\u00a0<em>both\u00a0<\/em> the 1- and 2- positions? In these cases, it turns out that the substituent on the 1-position is more powerful at directing the products. <em>[<span style=\"color: #993366;\">See <a style=\"color: #993366;\" href=\"#noteone\"><strong>Note 1<\/strong><\/a>]<\/span><\/em><\/p>\n<h2><strong><a id=\"four\"><\/a>4. Summary: Regiochemistry In The Diels-Alder Reaction<\/strong><\/h2>\n<p><strong>Avoid the <em>meta-<\/em> product <em>(1,3)<\/em>. That&#8217;s really it.<\/strong><\/p>\n<p>So\u00a0<em>why<\/em> does the Diels-Alder wind up this way?<\/p>\n<p>Good question.<\/p>\n<p>For the answer, read on&#8230;..<\/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\/2019\/11\/14\/the-cope-and-claisen-rearrangements\/\" class=\"\"><span>The Cope and Claisen Rearrangements<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/02\/09\/endo-exo-diels-alder-telling-them-apart\/\" class=\"\"><span>Exo vs Endo Products In The Diels Alder: How To Tell Them Apart<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2019\/12\/06\/the-intramolecular-diels-alder-reaction\/\" class=\"\"><span>The Intramolecular Diels Alder Reaction<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/11\/13\/stereochemistry-of-the-diels-alder-reaction\/\" class=\"\"><span>Stereochemistry of the Diels-Alder Reaction<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/09\/08\/cyclic-dienes-and-dienophiles-in-the-diels-alder-reaction\/\" class=\"\"><span>Cyclic Dienes and Dienophiles in the Diels-Alder Reaction<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/09\/03\/diels-alder-kinetic-thermodynamic-exo-endo\/\" class=\"\"><span>Diels-Alder Reaction: Kinetic and Thermodynamic Control<\/span><\/a><\/li><\/ul><\/div>\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\/3530-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\/3531-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\/3532-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\/3533-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\/3534-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\/3535-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<h2><strong>Understanding Regioselectivity<\/strong><\/h2>\n<p>It can be helpful to think of the diene as a <strong>nucleophile<\/strong> and the dienophile as the <strong>electrophile<\/strong>.<\/p>\n<p>The dominant product will be the one where the <strong>most nucleophilic carbon on the diene<\/strong> lines up with the <strong>most electrophilic carbon on the dienophile.<\/strong><\/p>\n<p>So how do we determine <strong>what<\/strong> these carbons are?<\/p>\n<ol>\n<li>Look for the second-best resonance form of the diene and the dienophile! (sometimes known as <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/10\/06\/grossmans-rule\/\">Grossman&#8217;s rule<\/a>)<\/li>\n<li>Line up the negative charge on the diene with the positive charge on the dienophile.<\/li>\n<\/ol>\n<p>This will get you to the right result!<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15737\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F1-rationalization-of-regiochemistry-in-diels-alder-reaction-look-for-second-best-resonance-form-line-up-opposite-charges.gif\" alt=\"rationalization of regiochemistry in diels alder reaction look for second best resonance form line up opposite charges\" width=\"600\" height=\"603\" \/><\/p>\n<p>Note how this results in the\u00a0<em>ortho<\/em>&#8211; product and not the\u00a0<em>meta-\u00a0<\/em>product, just like what&#8217;s observed in experiment.<\/p>\n<p>What about 2-substituted dienes?<\/p>\n<p>Same process. Draw out the &#8220;second-best&#8221; resonance form. Now line up the negative charge on the nucleophile with the positive charge on the &#8220;2nd best&#8221; resonance form of the electrophile:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15738\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F2-rationalize-regiochemistry-for-2-substituted-dienes-draw-second-best-resonance-form-line-up-opposite-charges.gif\" alt=\"rationalize regiochemistry for 2 substituted dienes draw second best resonance form line up opposite charges\" width=\"600\" height=\"422\" \/><\/p>\n<p>Note how this correctly predicts the\u00a0<em>para<\/em> product will be favored over the\u00a0<em>meta<\/em> product.<\/p>\n<p>That&#8217;s it.<\/p>\n<p>Now&#8230; is this <em>really<\/em> the best way to do it?<\/p>\n<p>For our purposes, yes.<\/p>\n<p>For more advanced purposes&#8230; we rely on\u00a0molecular orbital calculations. In advanced courses, we talk a lot about the size of &#8220;coefficients&#8221; on the HOMO or LUMO of the diene\/dienophile, and we&#8217;re not going there. If you are interested in this topic, I highly recommend Ian Fleming&#8217;s <a href=\"https:\/\/www.amazon.com\/Frontier-Orbitals-Organic-Chemical-Reactions\/dp\/0471018198\">Frontier Orbitals and Organic Chemical Reactions<\/a>. Classic book.<\/p>\n<h2><strong>What About 1,2-Substituted Dienes?<\/strong><\/h2>\n<p><strong><a id=\"noteone\"><\/a>Note 1. <\/strong>What if they&#8217;re <strong>both<\/strong> substituted? Here&#8217;s a practical example.<\/p>\n<p class=\"p2\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15739\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F3-regiochemistry-of-1-2-disubstituted-dines-in-diesl-alder-which-group-is-more-powerful-director-the-1-substituent-is.gif\" alt=\"regiochemistry of 1 2 disubstituted dines in diesl alder which group is more powerful director the 1 substituent is\" width=\"600\" height=\"485\" \/><\/p>\n<p>What&#8217;s observed is that the <strong>1-position on the diene has a greater influence on the product than the 2-position.<\/strong><\/p>\n<hr \/>\n<h2><a id=\"references\"><\/a>(Advanced) References and Further Reading<\/h2>\n<ol>\n<li><strong>Frontier molecular orbital theory of cycloaddition reactions<\/strong><br \/>\nKendall N. Houk<br \/>\n<em>Accounts of Chemical Research<\/em> <strong>1975,<\/strong> <em>8<\/em> (11), 361-369<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ar50095a001\">10.1021\/ar50095a001<\/a><\/li>\n<li><strong>Generalized frontier orbitals of alkenes and dienes. Regioselectivity in Diels-Alder reactions<\/strong><br \/>\nK. N. Houk<br \/>\n<em>Journal of the American Chemical Society<\/em> <strong>1973,<\/strong> <em>95<\/em> (12), 4092-4094<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00793a069\">10.1021\/ja00793a069<\/a><\/li>\n<li><strong>Modeling chemical reactivity. 1. Regioselectivity of Diels-Alder cycloadditions of electron-rich dienes with electron-deficient dienophiles<\/strong><br \/>\nD. Kahn, C. F. Pau, L. E. Overman, and Warren J. Hehre<br \/>\n<em>Journal of the American Chemical Society<\/em> <strong>1986,<\/strong> <em>108<\/em> (23), 7381-7396<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00283a038\">10.1021\/ja00283a038<\/a><\/li>\n<li><strong>Quantitative Characterization of the Local Electrophilicity of Organic Molecules. Understanding the Regioselectivity on Diels\u2212Alder Reactions<\/strong><br \/>\nLuis R. Domingo, M. Jos\u00e9 Aurell, Patricia P\u00e9rez, and Renato Contreras<br \/>\n<em>The Journal of Physical Chemistry A<\/em> <strong>2002,<\/strong> <em>106<\/em> (29), 6871-6875<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jp020715j\">10.1021\/jp020715j<\/a><\/li>\n<li><strong>The regioselectivity of the diels-alder reaction between a diene with an electron-donating substituent and a dienophile with an electron-donating substituent: a test case for frontier orbital theory<\/strong><br \/>\nIan Fleming, Federico L. Gianni, Talat Mah<br \/>\n<em>Tetrahedron Lett.<\/em> <strong>1976<\/strong>, <em>17<\/em> (11), 881-884<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/www.sciencedirect.com\/science\/article\/pii\/S0040403900929095\">10.1016\/S0040-4039(00)92909-5<\/a><br \/>\nBetter than the Ian Fleming of <em>James Bond<\/em> fame \u2013 but his book on Frontier Molecular Orbital theory is excellent and recommended for all advanced students of organic chemistry.<\/li>\n<li><strong>Regioselectivity in Hetero Diels\u2013Alder Reactions<\/strong><br \/>\nCarla Grosso, Marta Liber, Amadeu F. Brigas, Teresa M. V. D. Pinho e Melo, and Am\u00e9rico Lemos<br \/>\n<em>Journal of Chemical Education<\/em> <strong>2019,<\/strong> <em>96<\/em> (1), 148-152<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/acs.jchemed.7b00933\">10.1021\/acs.jchemed.7b00933<\/a><\/li>\n<li><strong>On the Brassard&#8217;s rule of regioselectivity in Diels\u2013Alder reactions between haloquinones and polar dienes<\/strong><br \/>\nMauricio Maldonado-Dom\u00ednguez, Karen Ruiz-P\u00e9rez, Oscar Gonz\u00e1lez-Antonio, Margarita Romero-\u00c1vila, Jos\u00e9 M\u00e9ndez-Stivalet and Blas Flores-P\u00e9rez<br \/>\n<em>RSC Adv.,<\/em> <strong>2016<\/strong>, <em>6<\/em>, 75194-75201<br \/>\n<strong>DOI<\/strong>:<a href=\"https:\/\/pubs.rsc.org\/en\/content\/articlelanding\/2016\/ra\/c6ra14073d#!divAbstract\"> 10.1039\/C6RA14073D<\/a><\/li>\n<li><strong>Origins of Regioselectivity of Diels\u2212Alder Reactions for the Synthesis of Bisanthraquinone Antibiotic BE-43472B<\/strong><br \/>\nAmy E. Hayden, Robert S. Paton, Jochen Becker, Yee Hwee Lim, K. C. Nicolaou, and K. N. Houk<br \/>\n<em>The Journal of Organic Chemistry<\/em> <strong>2010,<\/strong> <em>75<\/em> (3), 922-928<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo902572y\">10.1021\/jo902572y<\/a><br \/>\nExperimental and theoretical study on a particularly complex diene\/dienophile pairing.<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>Regiochemistry (&#8220;Regioselectivity&#8221;) In The Diels-Alder Reaction The Diels-Alder is an onion, and we just keep peeling back the layers. When non-symmetrical dienes react with non-symmetrical <\/p>\n","protected":false},"author":1,"featured_media":15729,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1163],"tags":[652,631,363,1309,482],"post_folder":[],"class_list":["post-12032","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-dienes-and-mo-theory","tag-constitutional-isomers","tag-diels-alder","tag-dienes","tag-dienophiles","tag-regioselectivity"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Regiochemistry In the Diels-Alder Reaction - Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"When non-symmetrical dienes react with non-symmetrical dienophiles in the Diels Alder reaction, two regioisomers are possible. 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