{"id":1664,"date":"2011-07-04T09:10:42","date_gmt":"2011-07-04T14:10:42","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=1664"},"modified":"2026-04-21T10:39:12","modified_gmt":"2026-04-21T15:39:12","slug":"common-blind-spot-intramolecular-reactions","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2011\/07\/04\/common-blind-spot-intramolecular-reactions\/","title":{"rendered":"Common Blind Spot: Intramolecular Reactions"},"content":{"rendered":"<p><strong>Intramolecular Reactions<\/strong><\/p>\n<ul>\n<li>An <strong>intra<\/strong>molecular reaction is when the nucleophile and electrophile are present on the same molecule.<\/li>\n<li>The bonds that form and break in an intramolecular reaction are no different than those that form and break in the &#8220;normal&#8221;, intermolecular reaction.<\/li>\n<li>However, a new <strong>ring<\/strong> is formed.<\/li>\n<li>BTW, this is consistently one of instructors&#8217; favorite ways to test reactions on exams, since it actually doesn&#8217;t involve any new concepts but &#8220;looks weird&#8221;.<\/li>\n<li>Test yourself at the bottom of this article with examples of intramolecular S<sub>N<\/sub>1 and S<sub>N<\/sub>2 reactions!<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-38571\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/11\/0-summary-of-intramolecular-reactions-versus-intermolecular-reactions-result-in-formation-of-a-ring-and-most-often-form-5-and-6-membered-rings.gif\" alt=\"summary of intramolecular reactions versus intermolecular reactions result in formation of a ring and most often form 5 and 6 membered rings\" width=\"640\" height=\"463\" \/><\/a><\/p>\n<p>So I bought a belt today (pleather, 75 cents at the Goodwill).\u00a0 and decided to show it off. This is me putting it together.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-14829\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-belt-analogy-for-intramolecular-nucleophilic-substitution-reactions.jpg\" alt=\"belt analogy for intramolecular nucleophilic substitution reactions\" width=\"550\" height=\"355\" srcset=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-belt-analogy-for-intramolecular-nucleophilic-substitution-reactions.jpg 1024w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-belt-analogy-for-intramolecular-nucleophilic-substitution-reactions-300x194.jpg 300w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-belt-analogy-for-intramolecular-nucleophilic-substitution-reactions-768x496.jpg 768w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-belt-analogy-for-intramolecular-nucleophilic-substitution-reactions-320x207.jpg 320w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-belt-analogy-for-intramolecular-nucleophilic-substitution-reactions-640x413.jpg 640w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-belt-analogy-for-intramolecular-nucleophilic-substitution-reactions-360x232.jpg 360w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-belt-analogy-for-intramolecular-nucleophilic-substitution-reactions-720x465.jpg 720w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-belt-analogy-for-intramolecular-nucleophilic-substitution-reactions-800x516.jpg 800w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-belt-analogy-for-intramolecular-nucleophilic-substitution-reactions-760x491.jpg 760w\" sizes=\"(max-width: 550px) 100vw, 550px\" \/><\/p>\n<p>This is what it looks like now:<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-14830\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-image-of-two-belts-together.jpg\" alt=\"image of two belts together\" width=\"550\" height=\"452\" srcset=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-image-of-two-belts-together.jpg 1516w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-image-of-two-belts-together-300x246.jpg 300w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-image-of-two-belts-together-768x631.jpg 768w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-image-of-two-belts-together-1024x841.jpg 1024w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-image-of-two-belts-together-320x263.jpg 320w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-image-of-two-belts-together-640x526.jpg 640w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-image-of-two-belts-together-360x296.jpg 360w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-image-of-two-belts-together-720x591.jpg 720w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-image-of-two-belts-together-1080x887.jpg 1080w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-image-of-two-belts-together-800x657.jpg 800w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-image-of-two-belts-together-1280x1051.jpg 1280w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-image-of-two-belts-together-760x624.jpg 760w\" sizes=\"(max-width: 550px) 100vw, 550px\" \/><\/p>\n<p>At this point you&#8217;re probably saying WTF: that&#8217;s not what a belt is supposed to look like when you put it together. That&#8217;s because I linked it together with my other belt.<\/p>\n<p>I say: broaden your horizons of how nucleophiles and electrophiles can meet.<\/p>\n<p>*****<\/p>\n<p>Here&#8217;s a typical reaction you meet early on in Org 2. Formation of an ether through the addition of an oxygen nucleophile to an alkyl halide. This is the Williamson ether synthesis. <span style=\"color: #993366;\">(<a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2014\/10\/24\/the-williamson-ether-synthesis\/\"><em>See post: The Williamson Ether Synthesis<\/em><\/a>)<\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-14831\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-formation-of-ethers-from-alcohol-and-alkyl-halide-in-presence-of-base-is-williamson-ether-reaction.gif\" alt=\"formation of ethers from alcohol and alkyl halide in presence of base is williamson ether reaction\" width=\"600\" height=\"176\" \/><\/p>\n<p>Makes some sense, right? Nucleophile, electrophile: give the product.<\/p>\n<p>Here&#8217;s the same reaction. Exactly the same. But a lot of students I talk to will look twice at it the first time they see it,\u00a0 not quite sure what to do.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-14832\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-sodium-hydroxide-as-base-with-alcohol-alkyl-halide-leading-to-cyclic-ether.gif\" alt=\"sodium hydroxide as base with alcohol alkyl halide leading to cyclic ether\" width=\"600\" height=\"142\" \/><\/p>\n<p>Different example: the Friedel Crafts acylation between aromatic rings and acyl halides.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-14833\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-example-of-friedel-crafts-acylation-reaction-benzene-alcl3-intermolecluar.gif\" alt=\"example of friedel crafts acylation reaction benzene alcl3 intermolecluar\" width=\"600\" height=\"170\" \/><\/p>\n<p>Then, here&#8217;s the exact same reaction. Common result: hesitation. What happens?<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-14834\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-apply-same-concepts-of-intermolecular-reaction-to-intramolecular-friedel-crafts.gif\" alt=\"apply same concepts of intermolecular reaction to intramolecular friedel crafts\" width=\"600\" height=\"160\" \/><\/p>\n<p>Last example: formation of esters from alcohols and carboxylic acids. The Fischer esterification. Once people see this, they usually find it straightforward.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-14835\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-fischer-esterification-reaction-intermolecular.gif\" alt=\"fischer esterification reaction intermolecular\" width=\"600\" height=\"142\" \/><\/p>\n<p>But then hand them this reaction, and it&#8217;s a stumper.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-16760\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2020\/01\/8-fischer-projection-intramolecular.gif\" alt=\"fischer projection intramolecular\" width=\"600\" height=\"188\" \/><\/p>\n<p>What do all of these reactions have in common?<\/p>\n<p><strong>When the nucleophile and electrophile are on the same molecule, they form RINGS.<\/strong><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-16761\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2020\/01\/9-examples-of-intramolecular-reactions-sn2-friedel-crafts-and-lactonization.gif\" alt=\"examples of intramolecular reactions sn2 friedel crafts and lactonization\" width=\"600\" height=\"342\" \/><\/p>\n<p>Because you&#8217;re probably used to seeing linear molecules &#8211; not chains &#8211; it looks <em>weird. \u00a0<\/em>But if you think about it, you&#8217;re already familiar with an example of this:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-14838\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/10-closing-a-belt-is-an-intramolecular-reaction.jpg\" alt=\"closing a belt is an intramolecular reaction\" width=\"459\" height=\"344\" srcset=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/10-closing-a-belt-is-an-intramolecular-reaction.jpg 1200w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/10-closing-a-belt-is-an-intramolecular-reaction-300x225.jpg 300w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/10-closing-a-belt-is-an-intramolecular-reaction-768x576.jpg 768w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/10-closing-a-belt-is-an-intramolecular-reaction-1024x768.jpg 1024w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/10-closing-a-belt-is-an-intramolecular-reaction-320x240.jpg 320w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/10-closing-a-belt-is-an-intramolecular-reaction-640x480.jpg 640w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/10-closing-a-belt-is-an-intramolecular-reaction-360x270.jpg 360w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/10-closing-a-belt-is-an-intramolecular-reaction-720x540.jpg 720w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/10-closing-a-belt-is-an-intramolecular-reaction-1080x810.jpg 1080w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/10-closing-a-belt-is-an-intramolecular-reaction-800x600.jpg 800w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/10-closing-a-belt-is-an-intramolecular-reaction-760x570.jpg 760w\" sizes=\"(max-width: 459px) 100vw, 459px\" \/><\/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\/2015\/06\/12\/intramolecular-reactions-of-alcohols-and-ethers\/\" class=\"\"><span>Intramolecular Reactions of Alcohols and Ethers<\/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\/05\/30\/intramolecular-friedel-crafts-reactions\/\" class=\"\"><span>Intramolecular Friedel-Crafts Reactions<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2022\/11\/16\/fischer-esterification\/\" class=\"\"><span>Fischer Esterification \u2013 Carboxylic Acid to Ester Under Acidic Conditions<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/12\/10\/the-robinson-annulation\/\" class=\"\"><span>The Robinson Annulation<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2022\/04\/14\/aldol-addition-and-condensation\/\" class=\"\"><span>Aldol Addition and Condensation Reactions<\/span><\/a><\/li><\/ul><\/div>\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\/2499-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<p><br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0154-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<p><br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0164-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<p><br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0190-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<p><br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0730-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<p><br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1382-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<p><br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1585-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<p><br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/2136-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<p><br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/2567-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<p><br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3157-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<p><br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/3303-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>(Advanced) References and Further Reading<\/h2>\n<p>Control of <em>intra- <\/em>vs. <em>inter-<\/em>molecular reactions is commonly done by <em>dilution<\/em>. The former are favored at very low concentrations (high dilution), to minimize the probability of the molecule reacting with another molecule of itself.<\/p>\n<ol>\n<li><strong>Ring closure reactions of bifunctional chain molecules<br \/>\n<\/strong>Gabriello Illuminati and Luigi Mandolini<strong><br \/>\n<\/strong><em>Accounts of Chemical Research<\/em> <strong>1981,<\/strong> <em>14<\/em> (4), 95-102<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ar00064a001\">1021\/ar00064a001<\/a><br \/>\nFig. 1 in this paper shows that the intramolecular formation of 5- and 6-membered rings is especially favored relative to other ring sizes.<\/li>\n<li><strong>Ring-closure reactions. 22. Kinetics of cyclization of diethyl (.omega.-bromoalkyl)malonates in the range of 4- to 21-membered rings. Role of ring strain<br \/>\n<\/strong>Maria Antonietta Casadei, Carlo Galli, and Luigi Mandolini<br \/>\n<em>Journal of the American Chemical Society<\/em> <strong>1984,<\/strong> <em>106<\/em> (4), 1051-1056<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00316a039\">1021\/ja00316a039<\/a><br \/>\nFigure 1 in this paper also plots the relationship between ring size and rate of intramolecular cyclization, with a pronounced global maximum for 5-membered rings. The authors state that cyclizations for 9-11 membered rings \u201c<em>should be run at concentrations of less than 10<sup>-6<\/sup> M in order to proceed free from polymerization<\/em>!\u201d.<\/li>\n<li><strong>Ring-closure reactions. 7. Kinetics and activation parameters of lactone formation in the range of 3- to 23-membered rings<br \/>\n<\/strong>Carlo Galli, Gabriello Illuminati, Luigi Mandolini, and Pasquale Tamborra<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em> <strong>1977,<\/strong> <em>99<\/em> (8), 2591-2597<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ja00450a031\">1021\/ja00450a031<\/a><br \/>\nEsterification can also take place intramolecularly to give lactones, and as to be expected, 5-membered rings are the most favored, followed by 4 and 6, then 7, then other ring sizes (see Table I).<\/li>\n<li><strong>Ring-closure reactions. 11. The activation parameters for the formation of four- to six-membered lactones from .omega.-bromoalkanoate ions. The role of the entropy factor in small- and common-ring formation<br \/>\n<\/strong>Luigi Mandolini<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em> <strong>1978,<\/strong> <em>100<\/em> (2), 550-554<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00470a032\">1021\/ja00470a032<\/a><br \/>\nAs shown in Fig. 2, D<em>S<sup>\u2021<\/sup><\/em> values for intramolecular cyclizations are fairly negative and of the same magnitude as D<em>H<sup>\u2021<\/sup><\/em> values, which is why it can be difficult to favor intramolecular reactions for large rings.<\/li>\n<li><strong>Cyclization and polymerization of .omega.-(bromoalkyl)dimethylamines<br \/>\n<\/strong>DeLos F. DeTar and Walter Brooks<strong><br \/>\n<\/strong><em>The Journal of Organic Chemistry<\/em> <strong>1978,<\/strong> <em>43<\/em> (11), 2245-2248<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo00405a033\">1021\/jo00405a033<\/a><\/li>\n<li><strong>Quantitative evaluation of steric effects in SN2 ring closure reactions<br \/>\n<\/strong>DeLos F. DeTar and Narender P. Luthra<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em> <strong>1980,<\/strong> <em>102<\/em> (13), 4505-4512<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ja00533a033\">1021\/ja00533a033<\/a><br \/>\nCyclic amines can also be formed via intramolecular reactions and are subject to the same principles \u2013 5- and 6-membered rings form fastest.<\/li>\n<li><strong>Neighboring Group Participation by Carbonyl Oxygen<br \/>\n<\/strong> J. Pasto and M. P. Serve<strong><br \/>\n<\/strong>Journal of the American Chemical Society<strong> 1965, <\/strong><em>87<\/em> (7), 1515-1521<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01085a019\">10.1021\/ja01085a019<\/a><br \/>\nIn this case, a carbonyl oxygen can aid with leaving group departure and form a cyclic ether, which is especially favored if a 5- or 6-membered ring is formed.<\/li>\n<li><strong>Rules for Ring Closure<br \/>\n<\/strong>Jack E. Baldwin<br \/>\n<em> Chem. Soc. Chem. Comm<\/em>. <strong>1976<\/strong>, 734-736<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.rsc.org\/en\/content\/articlelanding\/1976\/c3\/c39760000734#!divAbstract\">10.1039\/C39760000734<\/a><br \/>\nAn advanced topic, this introduces \u2018Baldwin\u2019s rules for ring closure\u2019, which allows one to predict whether a particular intramolecular ring-closing reaction is favorable based on ring size, the hybridization of the carbon atom at the reaction site, and the relationship (exocyclic or endocyclic) of the reacting bond to the forming ring. These rules are based on empirical observations of ring-closing reactions.<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>Intramolecular Reactions An intramolecular reaction is when the nucleophile and electrophile are present on the same molecule. The bonds that form and break in an <\/p>\n","protected":false},"author":1,"featured_media":38571,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1414],"tags":[200,562,321,558,560,243,559,561],"post_folder":[],"class_list":["post-1664","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-substitution-reactions","tag-electrophiles","tag-fischer-esterification","tag-friedel-crafts","tag-intramolecular","tag-mental-blocks","tag-nucleophiles","tag-rings","tag-williamson"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Common Blind Spot: Intramolecular Reactions &#8211; Master Organic Chemistry<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.masterorganicchemistry.com\/2011\/07\/04\/common-blind-spot-intramolecular-reactions\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Common Blind Spot: Intramolecular Reactions &#8211; Master Organic Chemistry\" \/>\n<meta property=\"og:description\" content=\"Intramolecular Reactions An intramolecular reaction is when the nucleophile and electrophile are present on the same molecule. 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