{"id":11016,"date":"2017-09-08T11:53:09","date_gmt":"2017-09-08T16:53:09","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=11016"},"modified":"2025-10-28T12:19:56","modified_gmt":"2025-10-28T17:19:56","slug":"cyclic-dienes-and-dienophiles-in-the-diels-alder-reaction","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2017\/09\/08\/cyclic-dienes-and-dienophiles-in-the-diels-alder-reaction\/","title":{"rendered":"Cyclic Dienes and Dienophiles in the Diels-Alder Reaction"},"content":{"rendered":"<p><strong>Cyclic Dienes (e.g. Cyclopentadiene) and Cyclic Dienophiles In The Diels-Alder Reaction<\/strong><\/p>\n<p>Last post in this series we introduced the <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/08\/30\/the-diels-alder-reaction\/\">Diels-Alder reaction<\/a>. We saw that no matter how complex the diene or dienophile, or no matter what substituents are attached, the pattern of bonds that form and break are always the same.<\/p>\n<p>That also goes for reactions of\u00a0<strong>cyclic<\/strong> dienes and dienophiles, although it takes practice to get used to it!<\/p>\n<p><strong><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-33955\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/01\/0-Summary-cyclic-dienes-and-dienophiles-in-the-diels-alder-cyclopentadiene-and-maleic-anhydride.gif\" alt=\"Summary-cyclic dienes and dienophiles in the diels alder cyclopentadiene and maleic anhydride\" width=\"640\" height=\"472\" \/><\/a><\/strong><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">The Bond-Forming \/ Bond Breaking Pattern Followed By All Diels-Alder Reactions<\/a><\/li>\n<li><a href=\"#two\">Cyclic Dienes and Dienophiles In The Diels-Alder<\/a><\/li>\n<li><a href=\"#three\">Applying The Key Diels-Alder Bond-Forming\/Bond-Breaking Pattern To A Cyclic Diene (Cyclopentadiene)<\/a><\/li>\n<li><a href=\"#four\">Putting Diels-Alder Products In Perspective<\/a><\/li>\n<li><a href=\"#five\">Example:\u00a0 1,3-Cyclohexadiene In The Diels-Alder Reaction<\/a><\/li>\n<li><a href=\"#six\">A Third Example Of A Cyclic Diene: Pyrone<\/a><\/li>\n<li><a href=\"#seven\">Cyclic Dienophiles In The Diels-Alder Reaction<\/a><\/li>\n<li><a href=\"#eight\">Trust The Pattern, Even With Weird-Looking Dienophiles<\/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. The Bond-Forming \/ Bond Breaking Pattern In All Diels-Alder Reactions<\/h2>\n<p>In the Diels Alder reaction, these three things\u00a0<strong><em>always\u00a0<\/em><\/strong>occur:<\/p>\n<ul>\n<li>3 pi bonds break<\/li>\n<li>2 sigma bonds and one new pi bond are formed<\/li>\n<li>A new six-membered ring is formed<\/li>\n<\/ul>\n<p>Here&#8217;s the basic pattern:<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15654\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-reprise-of-key-pattern-of-diels-alder-reaction-diene-plus-dienophile-giving-new-six-membered-ring-3-carbon-carbon-pi-bonds-broken-3-new-carbon-carbon-bonds-formed.gif\" alt=\"reprise of key pattern of diels alder reaction diene plus dienophile giving new six membered ring 3 carbon carbon pi bonds broken 3 new carbon carbon bonds formed\" width=\"600\" height=\"217\" \/><\/p>\n<h2><a id=\"two\"><\/a>2. Cyclic Dienes and Dienophiles In The Diels-Alder<\/h2>\n<p>OK. Let&#8217;s up the complexity a notch.<\/p>\n<p>It&#8217;s clear that the Diels-Alder forms a new, six-membered ring.<\/p>\n<p>But what if your diene is\u00a0<em>already<\/em> part of a ring?<\/p>\n<p>For instance, what would be the product of the following Diels-Alder?<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15655\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-diels-alder-cyclic-example-between-cyclopentadiene-and-alkene-what-does-the-product-look-like.gif\" alt=\"diels alder cyclic example between cyclopentadiene and alkene what does the product look like\" width=\"600\" height=\"202\" \/><a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2017\/09\/2-cyclic-part-2-e1504809456456.png\"><br \/>\n<\/a>If I had a duck for every time I&#8217;ve seen a student struggle with this example, there would be a hell of a lot of quacking in my backyard. I would also be in gross violation of local municipal bylaws on livestock. Hence, today&#8217;s post is devoted to cyclic dienes and dienophiles.<\/p>\n<h2><a id=\"three\"><\/a>3. Applying The Key Diels-Alder Bond-Forming\/Bond-Breaking Pattern To A Cyclic Diene (Cyclopentadiene)<\/h2>\n<p>My first suggestion with examples like this is that it might help to block out all the non-essential bits so you can focus on the core reaction. So let&#8217;s call the carbon that&#8217;s attached to both C-1 and C-4 , &#8220;C-7&#8221; and give it a color (grey) that lets us focus on the diene itself.\u00a0<a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2017\/09\/3-cyclic-part-3-1-e1504809959919.png\"><br \/>\n<\/a><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15656\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-to-discover-what-the-reaction-of-cyclopentadiene-with-alkenes-gives-what-product-it-might-be-helpful-to-greyscale-the-key-carbon-in-cyclopentadiene.gif\" alt=\"to discover what the reaction of cyclopentadiene with alkenes gives what product it might be helpful to greyscale the key carbon in cyclopentadiene\" width=\"630\" height=\"109\" \/><a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2017\/09\/3b-focus-cyclopent-e1504813252301.png\"><br \/>\n<\/a>Next, let&#8217;s apply the pattern.<\/p>\n<p>Does the pattern of bonds that form and break (above) say anything about breaking or forming a bond to C-7?\u00a0<strong>NO.\u00a0<\/strong><\/p>\n<p><em><strong>So don&#8217;t touch C-7!\u00a0<\/strong><\/em>\u00a0: &#8211; )<\/p>\n<p>Following the pattern\u00a0gives us the following molecule:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15657\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-diels-alder-reaction-of-cyclopentadiene-with-dienophile-giving-diels-alder-product-with-cyclopentadiene-carbon-greyscaled.gif\" alt=\"diels alder reaction of cyclopentadiene with dienophile giving diels alder product with cyclopentadiene carbon greyscaled\" width=\"600\" height=\"226\" \/><\/p>\n<h2><a id=\"four\"><\/a>4. Putting Diels-Alder Products In Perspective<\/h2>\n<p>Note that we&#8217;ve drawn the product molecule [2.2.1] bicyclo-2-heptene from a &#8220;birds&#8217; eye view&#8221; , i.e. from above. That&#8217;s the simplest way to do it. The trouble is that it doesn&#8217;t <em>really<\/em> convey the stereochemistry of the product.<\/p>\n<p>Hence, when a bicyclic product is formed, what you&#8217;ll often see is that it will be drawn in &#8220;perspective&#8221;, i.e.\u00a0<em>from the side<\/em>.<\/p>\n<p>This throws a lot of students off.<\/p>\n<p>Molecules are three dimensional objects just like many other items in our everyday lives. The difference is that you likely have much less familiarity with what molecules look like from various perspectives than you do with, say, cars.<\/p>\n<p>So here&#8217;s a quick analogy:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15658\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-diels-alder-products-in-perspective-are-not-unlike-looking-at-cars-from-either-the-top-or-the-side-its-the-same-car-same-with-molecules-top-view-side-view-of-bicyclic-product.gif\" alt=\"diels alder products in perspective are not unlike looking at cars from either the top or the side its the same car same with molecules top view side view of bicyclic product\" width=\"630\" height=\"374\" \/><\/p>\n<p>Make sense? I hope so.<\/p>\n<h2><a id=\"five\"><\/a>5.\u00a0 Example:\u00a0 1,3-Cyclohexadiene In The Diels-Alder Reaction<\/h2>\n<p>Alright. Let&#8217;s try another cyclic diene. How about 1,3-cyclohexadiene?<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15659\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-what-about-example-of-1-3-cyclohexadiene-with-dienophile-what-does-product-look-like.gif\" alt=\"what about example of 1 3 cyclohexadiene with dienophile what does product look like\" width=\"600\" height=\"254\" \/><\/p>\n<p>Again, if you focus on the diene itself without getting psyched out by the fact that it&#8217;s cyclic, \u00a0you should get the following product:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15666\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-diels-alder-reaction-of-cyclohexadiene-with-dienophile-gives-bicyclic-product-.gif\" alt=\"diels alder reaction of cyclohexadiene with dienophile gives bicyclic product\" width=\"600\" height=\"322\" \/><\/p>\n<p>As the size of the cyclic diene goes up, it gets progressively more difficult to draw the bridge in a way such that it fits inside the new six-membered ring. Two carbons is about the limit, and even that looks weird.<\/p>\n<p>So if you find that drawing the &#8220;side view&#8221; molecule throws you off, my (unpopular) advice is the following: find a molecular model kit and build the darn thing. \u00a0 #chemnagging<\/p>\n<h2><a id=\"six\"><\/a>6. A Third Example Of A Cyclic Diene: Pyrone<\/h2>\n<p>OK. Let&#8217;s finish up on dienes with a really wild-looking example. And this time we&#8217;ll use an a dienophile that is actually practical to use (<a href=\"https:\/\/en.wikipedia.org\/wiki\/Dimethyl_acetylenedicarboxylate\">dimethylacetylenedicarboxylate, or DMAD<\/a>) due to its electron withdrawing groups.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15660\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/8-what-about-diels-alder-reaction-of-pyrone-2-pyrone-with-dienophile-alkyne-with-pyrone.gif\" alt=\"what about diels alder reaction of pyrone 2 pyrone with dienophile alkyne with pyrone\" width=\"600\" height=\"247\" \/><\/p>\n<p>Wait &#8211; can acetylenes be used in the Diels-Alder?\u00a0<strong><em>Yes<\/em>,\u00a0<\/strong>especially if they are attached to electron withdrawing groups. Just treat them the way you&#8217;d treat a &#8220;normal&#8221; dienophile; break a C-C pi bond and leave the other one intact.<\/p>\n<p>Chances are high that you&#8217;ve never seen a pyrone before. It doesn&#8217;t matter.\u00a0Just trust in the pattern of bonds that form and break in the key pattern!<\/p>\n<p>Here&#8217;s what the product looks like.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15661\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/9-diels-alder-reaction-between-pyrone-and-alkyne-gives-the-same-pattern-of-bonds-formed-and-bonds-broken-with-alkyne-and-pyrone-drawn-in-perspective.gif\" alt=\"diels alder reaction between pyrone and alkyne gives the same pattern of bonds formed and bonds broken with alkyne and pyrone drawn in perspective\" width=\"630\" height=\"286\" \/><\/p>\n<p>Notice how using an alkyne in the Diels-Alder results in an additional alkene in the final product, since only one of its pi-bonds is broken.<\/p>\n<p>The &#8220;top-down&#8221; perspective looks really ugly. It&#8217;s difficult to fit the carbonyl into the six-membered ring (I had to cheat and increase the ring size). The &#8220;perspective&#8221; view looks much better, in my opinion. Your instructor will likely agree with me. \u00a0Therefore, get comfortable with interpreting the &#8220;perspective&#8221; view, especially for bridged bicyclic compounds.<\/p>\n<h2><strong><a id=\"seven\"><\/a>7. Cyclic Dienophiles In The Diels-Alder Reaction<\/strong><\/h2>\n<p>Dealing with cyclic dienophiles is slightly easier since they don&#8217;t lead to bridged bicyclic products. But they are still worth looking at.<\/p>\n<p>One of the most common cyclic dienophiles you&#8217;ll encounter is maleic anhydride:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15662\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/10-diels-alder-reaction-with-butadiene-and-a-cyclic-dienophile-giving-diels-alder-product-can-be-shown-with-stereochemistry.gif\" alt=\"diels alder reaction with butadiene and a cyclic dienophile giving diels alder product can be shown with stereochemistry\" width=\"630\" height=\"301\" \/><\/p>\n<p>We left out the stereochemistry here since today we&#8217;re just focused on getting the pattern of bonds that form and break correct.<span style=\"color: #993366;\"> <em>(although we did put the stereochemistry of the product in greyscale, below)<\/em><\/span><\/p>\n<h2><a id=\"eight\"><\/a>8. Trust The Pattern &#8211; Even With Weird-Looking Dienophiles!<\/h2>\n<p>Seem easy? Then let&#8217;s throw something weird at you. This is a super-hot dienophile called MTAD.<\/p>\n<p>Don&#8217;t let it psyche you out. Work through the pattern.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15663\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/11-diels-alder-reaction-of-cyclic-dienophile-with-diene-butadiene-dienophile-is-mtad-hetero-diels-alder-reaction.gif\" alt=\"diels alder reaction of cyclic dienophile with diene butadiene dienophile is mtad hetero diels alder reaction\" width=\"630\" height=\"267\" \/><\/p>\n<p>This is an example where the pi bond that is being broken is not a carbon-carbon pi bond. We call these reactions, &#8220;hetero Diels-Alder reactions&#8221; and you will likely not see them in an introductory course. However, <strong>the key pattern of breaking three pi bonds and forming two single bonds and a pi bond still holds.\u00a0<\/strong>The only difference is that we&#8217;re breaking an N-N pi bond instead of a C-C pi bond.<\/p>\n<p>The reactions above might look like gnarly, really weird looking examples, but wouldn&#8217;t you rather see them now rather than, say, \u00a0on an exam? And isn&#8217;t it good to know that no matter how weird, all of these reactions follow the same general pattern?<\/p>\n<p>TRUST THE PATTERN!<\/p>\n<p><strong>Next Post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/11\/13\/stereochemistry-of-the-diels-alder-reaction\/\">Stereochemistry of The Diels Alder Reaction<\/a><\/strong><\/p>\n<hr \/>\n<h2><strong><a id=\"notes\"><\/a>Notes<\/strong><\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><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\/2018\/11\/05\/regiochemistry-in-the-diels-alder-reaction\/\" class=\"\"><span>Regiochemistry In The Diels-Alder Reaction<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/05\/11\/endo-vs-exo-in-the-diels-alder-reaction\/\" class=\"\"><span>Why Are Endo vs Exo Products Favored in the Diels-Alder Reaction?<\/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\/2018\/03\/23\/molecular-orbitals-in-the-diels-alder-reaction\/\" class=\"\"><span>HOMO and LUMO In the Diels Alder Reaction<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/organic-chemistry-practice-problems\/diels-alder-practice-problems\/\" class=\"\"><span>Diels Alder Practice Problems (MOC Membership)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/05\/12\/s-cis-and-s-trans\/\" class=\"\"><span>s-cis and s-trans<\/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><strong><a id=\"noteone\"><\/a>Note 1. <\/strong>As noted, the stereochemistry of the products was mostly left out so that we could focus on the bond-forming \/ bond-breaking pattern.<\/p>\n<p>Let&#8217;s fill them in.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15664\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F1-products-of-cyclic-dienes-and-dienophiles-diels-alder-products-shown-with-stereochemistry-depicted.gif\" alt=\"products of cyclic dienes and dienophiles diels alder products shown with stereochemistry depicted\" width=\"600\" height=\"158\" \/><\/p>\n<p>Those &#8220;wedged&#8221; bonds drawn to the C-7 carbon indicate that the one-carbon &#8220;bridge&#8221; is pointing out of the page. Likewise the two-carbon bridge in the reaction with cyclohexadiene. This might seem like applied common sense, since a bridged bicyclic molecule where the C-1 bond is a wedge and the C-4 bond is a dash is geometrically impossible (try building a model).<\/p>\n<p>In the next post we&#8217;ll explore the rules for stereochemistry in the Diels-Alder by examining examples such as the following (below). See if you can discern the key pattern!<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15665\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F2-challenge-see-if-you-can-detect-stereochemistry-pattern-of-diels-alder-reaction-diene-stereochemistry-dienopile-stereochemistry.gif\" alt=\"challenge see if you can detect stereochemistry pattern of diels alder reaction diene stereochemistry dienopile stereochemistry\" width=\"600\" height=\"610\" \/><\/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\/3455-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\/3456-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\/3457-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\/3458-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\/3459-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\/3460-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","protected":false},"excerpt":{"rendered":"<p>Cyclic Dienes (e.g. Cyclopentadiene) and Cyclic Dienophiles In The Diels-Alder Reaction Last post in this series we introduced the Diels-Alder reaction. We saw that no <\/p>\n","protected":false},"author":1,"featured_media":33955,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1163],"tags":[1010,1259,1260,1258,1257,631,1249,1250,1256],"post_folder":[],"class_list":["post-11016","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-dienes-and-mo-theory","tag-bridged-bicyclic","tag-cyclic-diene","tag-cyclic-dienophile","tag-cyclohexadiene","tag-cyclopentadiene","tag-diels-alder","tag-diene","tag-dienophile","tag-maleic-anhydride"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Cyclic Dienes and Dienophiles in the Diels-Alder Reaction<\/title>\n<meta name=\"description\" content=\"Drawing the product when cyclic dienes such as cyclopentadiene perform Diels Alder reactions sometimes gives students a hard time. 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