{"id":995,"date":"2010-10-15T22:15:51","date_gmt":"2010-10-15T20:15:51","guid":{"rendered":"http:\/\/masterorganicchemistry.wordpress.com\/?p=995"},"modified":"2024-12-19T15:07:17","modified_gmt":"2024-12-19T21:07:17","slug":"the-many-many-ways-to-draw-butane","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2010\/10\/15\/the-many-many-ways-to-draw-butane\/","title":{"rendered":"The Many, Many Ways of Drawing Butane"},"content":{"rendered":"<p><strong>Molecules Can Be Drawn In Lots Of Different Ways<\/strong><\/p>\n<p>One of the skills you have to develop early in Org 1 is to learn the different conventions for drawing molecules.<\/p>\n<p>Let&#8217;s use butane as an example. Butane is pretty boring molecule, frankly. It&#8217;s four carbons in a row. Not much more to it than that.<\/p>\n<p>However, even a simple molecule like butane can be represented a TON of different ways. The point of this post is to demonstrate a sampling of the many reasonable ways to draw it (along with a few ridiculous ones).<\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-38648\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2024\/12\/0-summary-many-ways-of-depicting-butane-line-diagram-line-bond-structural-formula-newman-sawhorse-fischer.gif\" alt=\"summary-many ways of depicting butane line diagram line bond structural formula newman sawhorse fischer\" width=\"640\" height=\"606\" \/><\/a><\/p>\n<p>First of all we have the three standard naming conventions.<\/p>\n<ul>\n<li>The <strong>line bond drawing<\/strong> &#8211; The first way we learn: \u00a0clear, straightforward but lengthy.<\/li>\n<li>The <strong>condensed form<\/strong> &#8211; useful for simple molecules, and word-processor friendly &#8211; CH<sub>3<\/sub>CH<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>3<\/sub>.<\/li>\n<li><strong>Line drawings<\/strong> &#8211; The simplest, quickest, most effective way to draw molecules. Each line depicts a carbon-carbon bond, meaning that each &#8220;kink&#8221; in the chain (including the tips) represents a carbon atom. The trick here is to recognize that the carbon hydrogen bonds are &#8220;hidden&#8221; &#8211; meaning that even they&#8217;re not drawn, you&#8217;re supposed to know that they&#8217;re still there. (<span style=\"color: #993366;\"><em>See post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/06\/27\/hidden-hydrogens-hidden-lone-pairs-hidden-counterions\/\">Hidden Hydrogens, Hidden Lone Pairs, Hidden Counterions<\/a><\/em><\/span>)<\/li>\n<\/ul>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14218\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-three-textbook-ways-of-drawing-butane-bond-line-formula-condensed-formula-line-drawing.gif\" alt=\"three-textbook-ways-of-drawing-butane-bond-line-formula-condensed-formula-line-drawing\" width=\"550\" height=\"172\" \/><br \/>\n<span style=\"color: #000000;\">As you soon see, however, it&#8217;s common that you&#8217;ll see these conventions not strictly followed. For instance I know many chemists who shy away from depicting a methyl group as just a straight line, because they&#8217;re worried that it might get neglected altogether or confused as a hydrogen [<span style=\"color: #993366;\"><em>I do this a lot on this site by the way &#8211; hopefully it doesn&#8217;t cause any confusion<\/em><\/span>]. <\/span><\/p>\n<p><span style=\"color: #000000;\">So sometimes you see drawings like the following, which are hybrids of line drawings and condensed molecular formulae.<\/span><\/p>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14414\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-sometimes-portions-of-condensed-formula-and-line-drawings-get-combined.gif\" alt=\"sometimes-portions-of-condensed-formula-and-line-drawings-get-combined\" width=\"550\" height=\"335\" \/><br \/>\nNote that the CH<sub>3<\/sub> can also be drawn as H<sub>3<\/sub>C because that way it&#8217;s more clear that its a carbon that&#8217;s bound to the rest of the chain. The molecules are EXACTLY THE SAME\u00a0 &#8211; exactly the same &#8211; but written a different way purely for aesthetic purposes.<\/p>\n<p>It gets more complicated from there of course. The CH<sub>3<\/sub> group comes up so often that we have a common abbreviation for it &#8211; &#8220;Me&#8221;, for methyl. NOT to be confused with Metal. That&#8217;s different. We can also use abbreviations for ethyl (Et), propyl (Pr), butyl (Bu), and so on.<\/p>\n<p>So replacing &#8220;CH<sub>3<\/sub>&#8221; for &#8220;Me&#8221; we can draw the following.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14415\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-chemistry-abbreviations-can-lead-to-different-structures-eg-replace-ch3-with-me.gif\" alt=\"chemistry-abbreviations-can-lead-to-different-structures-eg-replace-ch3-with-me\" width=\"549\" height=\"303\" \/><\/p>\n<p>Note that while it&#8217;s ridiculous to do so, Et-Et would also be a way of depicting butane, as would Bu-H. Ridiculous because there are so many better ways to depict it, but technically they still represent butane.<\/p>\n<p>And it can get more complicated when we try to depict these molecules in 3D.<\/p>\n<p>The dash-wedge convention is our way of depicting 3D molecules on a flat page. A wedged bond is pointing &#8220;out&#8221; of the page &#8211; if you were wearing 3D goggles, you could almost imagine reaching out in front of you and grabbing it &#8211; while the dashed bonds represents bonds that point away from you, back behind the page.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14416\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-adding-dashes-and-wedges-can-also-complicate-matters-for-even-simple-molecules-like-butane.gif\" alt=\"adding-dashes-and-wedges-can-also-complicate-matters-for-even-simple-molecules-like-butane\" width=\"495\" height=\"302\" \/><\/p>\n<p>We could also use the line to depict the carbon skeleton, while drawing in the bonds to hydrogen as dashes and wedges to depict them in 3D. It takes some practice to do this properly to make sure that the carbons get properly represented as tetrahedra.<\/p>\n<p>Finally there&#8217;s the projections &#8211; the sawhorse, Newman, and Fischer projections.<\/p>\n<p>The <strong>sawhorse projection<\/strong> is a side-on way of depicting molecules that clearly shows different orientations that we obtain through bond rotation (i.e. conformations). It&#8217;s a slightly more easily grasped way of visualizing conformations than the Newman but probably not quite as useful so it isn&#8217;t used as much.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14417\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-sawhorse-newman-and-fischer-projections-of-butane-make-things-even-more-complicated.gif\" alt=\"sawhorse-newman-and-fischer-projections-of-butane-make-things-even-more-complicated\" width=\"495\" height=\"233\" \/><\/p>\n<p>The <strong>Newman projection<\/strong> differs from the sawhorse in that it&#8217;s a front view &#8211; we look along one of the carbon-carbon bonds, and the view of the back one is obscured except for its bonds. You can imagine this as being similar to our view of a solar eclipse, where the moon completely blocks our view of the sun except for the corona which sticks out along the edges. The purpose of the Newman projection is that it makes it easy to visualize conformations. (<span style=\"color: #993366;\"><em>See post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/02\/01\/assigning-rs-to-newman-projections-and-converting-newman-to-line-diagrams\/\">Converting Newman to Line Diagrams<\/a><\/em><\/span>)<\/p>\n<p>The original purpose of the <strong>Fischer projection <\/strong>was to provide a convention for easily depicting 3D molecules on a flat page, but this has largely been supplanted by the wedge and dash diagram.\u00a0 Although the Fischer projection is ordinarily not used for boring molecules like butane that lack any interesting stereochemistry, but you still see it used for molecules like sugars.\u00a0 You will definitely encounter it within the first few chapters of your textbook. (<span style=\"color: #993366;\"><em>See post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2019\/05\/21\/how-to-determine-r-and-s-configurations-on-a-fischer-projection\/\">Determining R\/S On A Fischer Projection<\/a><\/em><\/span>)<\/p>\n<p>The <strong>bottom line<\/strong> here is that it&#8217;s important to understand that even a simple molecule like butane can be depicted in many ways, and although you initially learn about the three <em>simple <\/em>types of drawings (line-bond, condensed, and line drawings) there are a lot of hybrid forms that get used. Furthermore, once stereochemistry comes into play, there are dashes and wedges to worry about, as well as the sawhorse, Newman, and Fischer projections.<\/p>\n<p>Just be aware of<\/p>\n<ol>\n<li>what each of the conventions <strong>represent<\/strong><\/li>\n<li>the common abbreviations (Me, Et, Pr, Bu..)<\/li>\n<li>the purpose\/use\u00a0 of each convention<\/li>\n<\/ol>\n<p>and you should be fine.<\/p>\n<hr \/>\n<h2>Notes<\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2019\/05\/21\/how-to-determine-r-and-s-configurations-on-a-fischer-projection\/\" class=\"\"><span>How To Determine R and S Configurations On A Fischer Projection<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/02\/01\/assigning-rs-to-newman-projections-and-converting-newman-to-line-diagrams\/\" class=\"\"><span>Assigning R\/S To Newman Projections (And Converting Newman To Line Diagrams)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/06\/27\/hidden-hydrogens-hidden-lone-pairs-hidden-counterions\/\" class=\"\"><span>Hidden Hydrogens, Hidden Lone Pairs, Hidden Counterions<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2020\/05\/29\/newman-projection-of-butane-and-gauche-conformation\/\" class=\"\"><span>Newman Projection of Butane (and Gauche Conformation)<\/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\/2011\/06\/20\/condensed-structural-formulas\/\" class=\"\"><span>Condensed Formulas: Deciphering What the Brackets Mean<\/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\/2011\/06\/20\/condensed-structural-formulas\/\" class=\"\"><span>Condensed Formulas: Deciphering What the Brackets Mean<\/span><\/a><\/li><\/ul><\/div>\n","protected":false},"excerpt":{"rendered":"<p>Molecules Can Be Drawn In Lots Of Different Ways One of the skills you have to develop early in Org 1 is to learn the <\/p>\n","protected":false},"author":1,"featured_media":38648,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1408],"tags":[677,311,676,599,603,330,408,621,242,604],"post_folder":[],"class_list":["post-995","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alkanes-nomenclature","tag-abbreviations","tag-alkanes","tag-bond-rotations","tag-conformations-2","tag-dashes","tag-drawing","tag-hidden-hydrogens","tag-newman-projections","tag-nomenclature","tag-wedges"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>The Many, Many Ways of Drawing Butane &#8211; 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