{"id":596,"date":"2010-07-09T21:34:20","date_gmt":"2010-07-09T19:34:20","guid":{"rendered":"http:\/\/masterorganicchemistry.wordpress.com\/?p=596"},"modified":"2025-08-27T14:36:56","modified_gmt":"2025-08-27T19:36:56","slug":"branching-melting-boiling-points","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2010\/07\/09\/branching-melting-boiling-points\/","title":{"rendered":"Branching, and Its Affect On Melting and Boiling Points"},"content":{"rendered":"<p><strong>The Effect of Branching On Melting and Boiling Points<\/strong><\/p>\n<ul>\n<li>Recall that alkanes are hydrocarbons with the general formula C<sub>n<\/sub>H<sub>(n+2)<\/sub><\/li>\n<li>Isomers of hydrocarbons show regular trends with their melting and boiling points<\/li>\n<li>Generally, the\u00a0<strong>linear<\/strong> alkane isomer in each series (e.g. <em>n<\/em>-hexane) will have the highest boiling point, and the boiling point <strong>decreases <\/strong>as <strong>branching <\/strong>increases.<\/li>\n<li>This is because the intermolecular forces in liquids are proportional to surface area (due to London dispersion forces), and branching <strong>decreases <\/strong>surface area.<\/li>\n<li>For melting points, increased\u00a0<strong>symmetry<\/strong> results in higher melting points since the more regular an alkane &#8220;brick&#8221; is, the easier it is to stack.<\/li>\n<li>Relative to the branched isomers, the linear alkane isomer also tends to have a relatively high <strong>melting point<\/strong> since it is more symmetrical.<\/li>\n<li>However, with extreme branching can also come added symmetry, which can result in anomalously high melting points. One example is\u00a0<strong>neopentane\u00a0<\/strong>(2,2-dimethylpropane) which has a much higher melting point (-16\u00b0C)\u00a0 than that of pentane (-130\u00b0C).<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-37733\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/10\/0-Summary-Melting-Boiling-Points-Symmetry-and-Surface-Area.gif\" alt=\"Summary-Melting-Boiling Points Symmetry and Surface Area\" width=\"640\" height=\"427\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li style=\"list-style-type: none;\">\n<ol>\n<li><a href=\"#one\">Better Stacking=\u00a0 Higher Melting Points<\/a><\/li>\n<li><a href=\"#two\">Higher Surface Area = Higher Boiling Points<\/a><\/li>\n<li><a href=\"#three\">The Key Trends<\/a><\/li>\n<li><a href=\"#four\">Some More Experimental Data: Isomers of Heptane and Octane<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quizzes\">Quiz Yourself!\u00a0<\/a><\/li>\n<\/ol>\n<\/li>\n<\/ol>\n<h2><strong><a id=\"one\"><\/a>1. Better Stacking = Higher Melting Points<\/strong><\/h2>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14418\" title=\"chemtris\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-tetris-game-on-the-green-building-mit-terrible-game-of-tetris-on-my-part.jpg\" alt=\"tetris-game-on-the-green-building-mit-terrible-game-of-tetris-on-my-part\" width=\"455\" height=\"341\" srcset=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-tetris-game-on-the-green-building-mit-terrible-game-of-tetris-on-my-part.jpg 640w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-tetris-game-on-the-green-building-mit-terrible-game-of-tetris-on-my-part-300x225.jpg 300w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-tetris-game-on-the-green-building-mit-terrible-game-of-tetris-on-my-part-320x240.jpg 320w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-tetris-game-on-the-green-building-mit-terrible-game-of-tetris-on-my-part-360x270.jpg 360w\" sizes=\"(max-width: 455px) 100vw, 455px\" \/><\/p>\n<p>The above photo shows what is perhaps one of the worst games of Tetris ever played. In my defence, the point wasn&#8217;t so much to play, but to take a photo of the great setup the <a href=\"http:\/\/tmrc.mit.edu\/\">Tech Model Railroad Club <\/a>had set up next to the MIT museum, complete with a replica of the Green Building that you can play Tetris on. Truly the nerdiest place on earth.<\/p>\n<p>Tetris is essentially a bricklaying game on a timer. You&#8217;re given tiles and you have to rotate them so that you make &#8220;lines&#8221; at the bottom, which promptly disappear when complete. If there are any spaces left in between, they remain &#8211; (for many examples, just look above).\u00a0What makes Tetris hard is the arrangement of the different shapes. You often have to rotate them in order to get them to stack correctly.<\/p>\n<p>If you want to make the game absurdly easy, just make it such that every tile looks like the one on the left. Or difficult, to the piece on the right.<\/p>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14419\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-tetris-and-ease-o-f-stacking-blocks-pieces-that-are-regular-shaped-are-easy-to-stack-irregluar-pieces-are-hard.gif\" alt=\"tetris-and-ease-o-f-stacking-blocks-pieces-that-are-regular-shaped-are-easy-to-stack-irregluar-pieces-are-hard\" width=\"545\" height=\"206\" \/><\/p>\n<p>You&#8217;ll notice something &#8211; the simpler the pieces are, the easier they are to stack together, which provides a tighter fit with fewer spaces. Here, by putting a kink in the block, we make them harder to stack.<\/p>\n<p>What&#8217;s this got to do with chemistry?<\/p>\n<p>When compounds freeze, the process is a lot like stacking bricks. The more symmetrical the molecules are, the easier it will be \u00a0and the fewer spaces there will be between the molecules. Fewer spaces = better stacking. Hence, when you compare hexane to its structural isomer, 2-methylpentane, hexane has a much higher melting point due to the regular arrangement of its structure.<\/p>\n<p>Better stacking, higher melting point. Case closed. Right? Not quite.<\/p>\n<h2><strong><a id=\"two\"><\/a>2. Higher Surface Area = Higher Boiling Points<\/strong><\/h2>\n<p>It&#8217;s a nice story: branching decreases melting point and boiling point. But it gets more complicated.<\/p>\n<p>Look at these three examples of branched hexane derivatives (with hexane for comparison)<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14217\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-influence-of-structure-on-boiling-points-and-melting-points-greater-surface-area-leads-to-higher-boiling-point-linear-also-greater-symmetry-leads-to-higher-melting-points.gif\" alt=\"influence-of-structure-on-boiling-points-and-melting-points-greater-surface-area-leads-to-higher-boiling-point-linear-also-greater-symmetry-leads-to-higher-melting-points.\" width=\"600\" height=\"362\" \/><\/p>\n<p>It looks like as we increase branching, we&#8217;re increasing melting point and decreasing boiling point. What&#8217;s going on?<\/p>\n<p>Treat the n-hydrocarbon as a special case, and ignore it for the time being.\u00a0 Starting with the simplest branched compound, as you increase branching, you will <strong>increase <\/strong>the melting point, but <strong>decrease <\/strong>the boiling point. <strong>Why?<\/strong><\/p>\n<p>Going from &#8220;branched&#8221; to &#8220;highly branched&#8221;\u00a0 makes a molecule more compact and sphere-like. As the surface area of the molecule decreases (remember that spheres have the lowest surface area\/volume ratio of any shape) they will become more compact and thus easier to pack. This explains the melting point phenomenon.<\/p>\n<p>What about boiling point?<\/p>\n<p>Boiling point is related to the forces between molecules, which in the case of hydrocarbons is Van Der Waals interactions. If you&#8217;ve ever seen microscope images of a gecko&#8217;s feet &#8211; which allow it to climb walls &#8211; you&#8217;ll see that there is no adhesive but the pads contain a tremendous amount of surface area. It&#8217;s all about the Van der Waals interactions.<\/p>\n<p>As we<em> decrease<\/em> surface area, we are going to <em>decrease<\/em> intermolecular Van Der Waals interaction and therefore decrease boiling point.<\/p>\n<h2><a id=\"three\"><\/a>3. The Key Relationships<\/h2>\n<p>So here are the relationships:<\/p>\n<p><strong>linear versus branched &#8212;&gt; higher melting\/boiling points due to better stacking and surface area contact. <\/strong><\/p>\n<p><strong>highly branched vs. branched &#8212;&gt; more sphere-like &#8211;&gt; better stacking &#8211;&gt; higher melting point<\/strong><\/p>\n<p><strong>highly branched vs. branched \u00a0&#8212;&gt;more sphere-like &#8211; -&gt; lower surface area &#8212;&gt; lower boiling point.<\/strong><\/p>\n<p>If this all seems rather ambiguous, contradictory, and imprecise, well, you have a point. It&#8217;s not a straightforward topic. As a final example, I give you 2,2,3,3,-tetramethylbutane. An isomer of isooctane (gasoline) with melting point 95 \u00b0C. Further proof, as if more was needed, that predicting melting\/boiling points from chemical structures can be a fool&#8217;s errand.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"37745\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"37745\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"37745\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"37745\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-37745\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-37745 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"37745\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-md8p7\" data-id=\"md8p7\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/3004-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/3004-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<h2><a id=\"four\"><\/a>4. Some More Experimental Data: Isomers of Heptane and Octane<\/h2>\n<p>Looking at some experimental data, here are some isomers of heptane.<\/p>\n<p>Note how the boiling point decreases as branching decreases (less surface area!) and the melting point also decreases with branching, but only to a point. The isomer 2,2,3-trimethylbutane has a higher melting point (-25\u00b0C) than linear heptane.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-37734\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/10\/5-boiling-point-and-melting-point-data-for-some-isomers-of-heptane-c7h16.gif\" alt=\"boiling point and melting point data for some isomers of heptane c7h16\" width=\"640\" height=\"417\" \/><\/a><\/p>\n<p>A similar phenomenon is observed for isomers of octane (C<sub>8<\/sub>H<sub>18<\/sub>). Note how the boiling points decrease with branching, but it&#8217;s a different story with the melting points. In particular, 2,2,3,3-tetramethylbutane is a solid at room temperature owing to its highly symmetrical structure.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-37735\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/10\/6-boiling-point-and-melting-point-data-for-some-isomers-of-octane.gif\" alt=\"boiling point and melting point data for some isomers of octane\" width=\"640\" height=\"390\" \/><\/a><\/p>\n<p>&nbsp;<\/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\/2010\/10\/01\/how-intermolecular-forces-affect-boiling-points\/\" class=\"\"><span>The Four Intermolecular Forces and How They Affect Boiling Points<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/10\/25\/3-trends-that-affect-boiling-points\/\" class=\"\"><span>3 Trends That Affect Boiling Points<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/11\/10\/dont-be-futyl-learn-the-butyls\/\" class=\"\"><span>Don\u2019t Be Futyl, Learn The Butyls<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/10\/15\/the-many-many-ways-to-draw-butane\/\" class=\"\"><span>The Many, Many Ways of Drawing Butane<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/06\/16\/1-2-3-4\/\" class=\"\"><span>Primary, Secondary, Tertiary, Quaternary In Organic Chemistry<\/span><\/a><\/li><\/ul><\/div>\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\/1243-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\/1244-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\/1247-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\/3357-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\/3358-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\/3359-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>The Effect of Branching On Melting and Boiling Points Recall that alkanes are hydrocarbons with the general formula CnH(n+2) Isomers of hydrocarbons show regular trends <\/p>\n","protected":false},"author":1,"featured_media":37733,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1408],"tags":[179,674,750,419,234,752,247,749,751,649,675],"post_folder":[],"class_list":["post-596","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alkanes-nomenclature","tag-boiling-points","tag-branching","tag-forces","tag-fun","tag-melting-points","tag-mit","tag-org-1-2","tag-stacking","tag-surface-area","tag-symmetry","tag-van-der-waals"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Branching, and Its Affect On Melting and Boiling Points<\/title>\n<meta name=\"description\" content=\"So here are the key relationships between branching and melting\/boiling points: linear versus branched ---&gt; higher melting\/boiling points due to better stacking and surface area contact. highly branched vs. branched ---&gt; more sphere-like --&gt; better stacking --&gt; higher melting point highly branched vs. branched \u00a0---&gt;more sphere-like - -&gt; lower surface area ---&gt; lower boiling point.\" \/>\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\/2010\/07\/09\/branching-melting-boiling-points\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Branching, and Its Affect On Melting and Boiling Points\" \/>\n<meta property=\"og:description\" content=\"So here are the key relationships between branching and melting\/boiling points: linear versus branched ---&gt; higher melting\/boiling points due to better stacking and surface area contact. highly branched vs. branched 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