{"id":7967,"date":"2014-02-18T16:25:19","date_gmt":"2014-02-18T21:25:19","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=7967"},"modified":"2025-10-03T14:00:37","modified_gmt":"2025-10-03T19:00:37","slug":"introduction-to-cycloalkanes-1","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2014\/02\/18\/introduction-to-cycloalkanes-1\/","title":{"rendered":"Introduction to Cycloalkanes"},"content":{"rendered":"<p><strong>Cycloalkanes: Two Key Consequences of The Fact That Hydrocarbons Can Form Rings<\/strong><\/p>\n<p style=\"text-align: left;\">In the first few weeks of an organic chemistry class, we&#8217;ve learned that:<\/p>\n<ul>\n<li>Carbon can form up to<strong> four<\/strong> single bonds<\/li>\n<li>Carbon with four single bonds adopts a<strong> tetrahedral<\/strong> geometry (ideal bond angle: 109.5\u00b0)<\/li>\n<li>Compared to other atoms on the periodic table, [O, N, S, Si for example] <strong>carbon forms very strong bonds with itself<\/strong> and can therefore form <strong>stable chains<\/strong><\/li>\n<li>Carbon-carbon single bonds can<strong> rotate freely<\/strong>, and the three-dimensional shapes that arise (&#8220;<strong>conformations&#8221;<\/strong>)<strong> can vary significantly in energy.\u00a0<\/strong><\/li>\n<\/ul>\n<p>Nothing particularly strange about that so far. How about this:<\/p>\n<ul>\n<li>in addition to forming chains, carbon atoms can also form\u00a0<strong>rings!<\/strong><\/li>\n<\/ul>\n<p>In this first post on this series on cycloalkanes, we&#8217;ll discuss two key consequences of the fact that carbon can form rings, and then move forward with further posts in that vein.<\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-38608\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/11\/0-consequences-of-cycloalkanes-one-consequence-is-that-the-hydrogen-count-goes-down-by-2-for-cycloalkanes-another-is-cis-trans-isomerism.gif\" alt=\"consequences of cycloalkanes - one consequence is that the hydrogen count goes down by 2 for cycloalkanes another is cis trans isomerism\" width=\"640\" height=\"573\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Each Ring Decreases The Hydrogen Count By Two<\/a><\/li>\n<li><a href=\"#two\">Cycloalkanes of Less Than 8 Carbons Cannot Be Turned Inside-Out Without Breaking Carbon-Carbon Bonds<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><strong><a id=\"one\"><\/a>1. Each Ring Decreases The Hydrogen Count By Two<\/strong><\/h2>\n<p style=\"text-align: left;\">One of the first consequences of the fact that carbon can form rings can be found by comparing the condensed molecular formulae of linear alkanes with cyclic alkanes.<\/p>\n<p style=\"text-align: left;\">Notice how the formula of linear alkanes follows the pattern \u00a0 H = 2n + 2 \u00a0(where &#8220;n&#8221; is the number of carbons) whereas the formula for cycloalkanes follows the pattern H = 2n.<\/p>\n<p style=\"text-align: left;\">Just by forming a ring, the number of hydrogens decreases by two!<\/p>\n<p style=\"text-align: left;\"><img decoding=\"async\" class=\"alignnone wp-image-42095\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/09\/1-cycloalkanes-molecular-formula-each-ring-decreases-the-hydrogen-count-by-two.gif\" alt=\"cycloalkanes molecular formula each ring decreases the hydrogen count by two\" width=\"640\" height=\"458\" \/><\/a><\/p>\n<p>By the way, <strong>every successive ring decreases the hydrogen content by two<\/strong> &#8211; the bicyclic molecules below follow each follow the pattern #H = 2n \u20132.<\/p>\n<p>And the tricyclic molecule follows the pattern #H = 2n \u20134 .<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-42096\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/09\/2-bicyclic-molecule-c10-h18-c6h10-c12h20-rings-decrease-h-count-by-2.gif\" alt=\"bicyclic molecule c10 h18 c6h10 c12h20 rings decrease h count by 2\" width=\"640\" height=\"337\" \/><\/a><\/p>\n<p><span style=\"color: #993366;\"><em>[Bonus Q &#8211; how many hydrogens would be in a tetracyclic molecule with 20 carbons (and no multiple bonds)? ]<\/em><\/span><\/p>\n<p>Why does this matter? As you&#8217;ll see later, we&#8217;ll be able to use the fact that each ring decreases the hydrogen count of the molecule by 2 to help us deduce the structures of unknown compounds in some cases. It can be a small clue, but an important one nonetheless. <span style=\"color: #993366;\"><em>[A look ahead &#8211; <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2016\/08\/26\/degrees-of-unsaturation-index-of-hydrogen-deficiency\/\">Degree of Unsaturation<\/a>]<\/em><\/span><\/p>\n<h2><strong><a id=\"two\"><\/a>2. Cycloalkanes Of Less Than 8 Carbons Cannot Be Turned Inside-Out Without Breaking Carbon-Carbon Bonds<\/strong><\/h2>\n<p>There&#8217;s a second interesting observation with cycloalkanes that we&#8217;ll talk about in much greater detail next time, but is important to get out of the way because it&#8217;s often overlooked. See how there&#8217;s that empty space in the middle of a cycloalkane ring? Many everyday household objects &#8211; belts, elastics, wristbands &#8211; can be easily turned inside out. Can we do the same with cycloalkanes? <strong>What happens when we try to turn them inside out?\u00a0<\/strong><\/p>\n<p><b>\u00a0<\/b>Because it&#8217;s much easier to show this rather than tell it, I\u00a0made a quick video.<\/p>\n<p><iframe title=\"YouTube video player\" src=\"https:\/\/www.youtube.com\/embed\/kSqvjKosEpg?si=V0VmSpv0lYJx_ayT\" width=\"560\" height=\"315\" frameborder=\"0\" allowfullscreen=\"allowfullscreen\"><\/iframe><\/p>\n<p>The bottom line is that cycloalkanes of less than 8 carbons\u00a0<strong>cannot be turned inside out<\/strong> without breaking carbon-carbon bonds. \u00a0&gt;99% of the rings that you&#8217;ll see in Org 1 \/ Org 2 will fall into this category.<\/p>\n<p>This has far-ranging consequences that we&#8217;ll talk about in the next post in this series, namely that it gives rise to &#8220;cis&#8221; and &#8220;trans&#8221; isomers that cannot be interconverted.<\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/03\/20\/cycloalkanes-cis-and-trans\/\">Next Post: Cis and Trans Cycloalkanes<\/a><\/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\/2014\/03\/20\/cycloalkanes-cis-and-trans\/\" class=\"\"><span>Geometric Isomers In Small Rings: Cis And Trans Cycloalkanes<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/09\/10\/types-of-isomers\/\" class=\"\"><span>Types of Isomers: Constitutional Isomers, Stereoisomers, Enantiomers, and Diastereomers<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/08\/26\/degrees-of-unsaturation-index-of-hydrogen-deficiency\/\" class=\"\"><span>Degrees of Unsaturation (or IHD, Index of Hydrogen Deficiency)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/04\/18\/ring-strain-in-cyclopentane-and-cyclohexane\/\" class=\"\"><span>Cyclohexane Conformations<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/05\/30\/the-cyclohexane-chair-flip\/\" class=\"\"><span>The Cyclohexane Chair Flip<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/11\/03\/alkene-nomenclature-cis-and-trans-and-e-and-z\/\" class=\"\"><span>E and Z Notation For Alkenes (+ Cis\/Trans)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/08\/05\/fused-rings\/\" class=\"\"><span>Fused Rings \u2013 Cis-Decalin and Trans-Decalin<\/span><\/a><\/li><\/ul><\/div>\n<p>The fact that cycloalkanes form rings has all kinds of consequences that are hard to\u00a0 foresee until you&#8217;re confronted with them.<\/p>\n<p>Let&#8217;s make a gratuitous chess analogy.<\/p>\n<p><span style=\"line-height: 1.5em;\">\u00a0One important rule in chess is that if a pawn makes its way to the end of the board, it can be promoted to a piece of the players choice.<\/span><\/p>\n<p><span style=\"line-height: 1.5em;\"> 99% of the time, the best choice is a Queen, but there are (very rare) situations where it is optimal to promote to a different piece &#8211; a knight, for example (see below). [<\/span><a style=\"line-height: 1.5em;\" href=\"http:\/\/chess.stackexchange.com\/questions\/730\/why-would-one-promote-a-pawn-to-a-knight\">link<\/a><span style=\"line-height: 1.5em;\">]<\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"wp-image-14264 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F1-analogy-of-simple-rules-leading-to-complex-results-the-fork-in-chess.png\" alt=\"F1-analogy-of-simple-rules-leading-to-complex-results-the-fork-in-chess\" width=\"585\" height=\"360\" srcset=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F1-analogy-of-simple-rules-leading-to-complex-results-the-fork-in-chess.png 653w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F1-analogy-of-simple-rules-leading-to-complex-results-the-fork-in-chess-300x185.png 300w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F1-analogy-of-simple-rules-leading-to-complex-results-the-fork-in-chess-320x197.png 320w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F1-analogy-of-simple-rules-leading-to-complex-results-the-fork-in-chess-640x394.png 640w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F1-analogy-of-simple-rules-leading-to-complex-results-the-fork-in-chess-360x222.png 360w\" sizes=\"(max-width: 585px) 100vw, 585px\" \/><\/p>\n<p>Cool, huh? An example like this one flows logically from the rules of the game, but <strong>you can&#8217;t really imagine situations like this one until you have a lot of board time under your belt.<\/strong><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Cycloalkanes: Two Key Consequences of The Fact That Hydrocarbons Can Form Rings In the first few weeks of an organic chemistry class, we&#8217;ve learned that: <\/p>\n","protected":false},"author":1,"featured_media":38608,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1409],"tags":[632,965,559,966],"post_folder":[],"class_list":["post-7967","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-conformations-cycloalkanes","tag-bicyclic","tag-cycloalkanes","tag-rings","tag-tricyclic"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - 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bonds.","breadcrumb":{"@id":"https:\/\/www.masterorganicchemistry.com\/2014\/02\/18\/introduction-to-cycloalkanes-1\/#breadcrumb"},"inLanguage":"en-US","potentialAction":[{"@type":"ReadAction","target":["https:\/\/www.masterorganicchemistry.com\/2014\/02\/18\/introduction-to-cycloalkanes-1\/"]}]},{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.masterorganicchemistry.com\/2014\/02\/18\/introduction-to-cycloalkanes-1\/#primaryimage","url":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/11\/0-consequences-of-cycloalkanes-one-consequence-is-that-the-hydrogen-count-goes-down-by-2-for-cycloalkanes-another-is-cis-trans-isomerism.gif","contentUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/11\/0-consequences-of-cycloalkanes-one-consequence-is-that-the-hydrogen-count-goes-down-by-2-for-cycloalkanes-another-is-cis-trans-isomerism.gif","width":900,"height":806,"caption":"consequences of cycloalkanes - one consequence is that the hydrogen count goes down by 2 for cycloalkanes another is cis trans isomerism"},{"@type":"BreadcrumbList","@id":"https:\/\/www.masterorganicchemistry.com\/2014\/02\/18\/introduction-to-cycloalkanes-1\/#breadcrumb","itemListElement":[{"@type":"ListItem","position":1,"name":"Home","item":"https:\/\/www.masterorganicchemistry.com\/"},{"@type":"ListItem","position":2,"name":"Introduction to Cycloalkanes"}]},{"@type":"WebSite","@id":"https:\/\/www.masterorganicchemistry.com\/#website","url":"https:\/\/www.masterorganicchemistry.com\/","name":"Master Organic 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