{"id":26151,"date":"2023-11-06T15:51:06","date_gmt":"2023-11-06T21:51:06","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=26151"},"modified":"2023-12-14T22:37:39","modified_gmt":"2023-12-15T04:37:39","slug":"bond-rotation-how-to-draw","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2023\/11\/06\/bond-rotation-how-to-draw\/","title":{"rendered":"How To Draw A Bond Rotation"},"content":{"rendered":"<p><strong>How To Draw A Bond Rotation<\/strong><\/p>\n<ul>\n<li>Rotation can happen to an infinitesimal extent around carbon-carbon single bonds but for the most part we only really care about showing rotations in <strong>60 degree increments<\/strong>. This keeps two groups in the plane of the page.<\/li>\n<li>Rotations of +120\u00b0 or -120\u00b0 can be shown simply by\u00a0<strong>interchanging any three groups on a carbon.\u00a0<\/strong>If the carbon is a chiral center, take special care that 3 groups are interchanged, otherwise this will result in inversion of configuration (a &#8220;single swap&#8221;) on the chiral center.<\/li>\n<li>Bond rotations\u00a0<em>never<\/em> result in flipping the absolute configuration of a carbon from (R) to (S) or vice versa, since that would involve breaking bonds. All that&#8217;s happening in a bond rotation is showing the molecule in a different conformation.<\/li>\n<li>Rotations of 180\u00b0 are useful because they allow for rotation of the entire carbon chain. When you&#8217;re just getting started, applying some simple templates can help with getting things right, as will using a model kit (or even your hands).<\/li>\n<li>Rotations of +60\u00b0 or -60\u00b0 are necessary less often than 180\u00b0 rotations, but they do use the same template as rotations of 180\u00b0.<\/li>\n<li>For situations where you need to rotate a large number of bonds at the same time, it&#8217;s often better to completely redraw the carbon chain and just make sure each chiral carbon has the same configuration in your &#8220;new&#8221; configuration as it does in the &#8220;old&#8221; one.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-35767\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/11\/0-summary-how-to-do-a-bond-rotation-of-120-180-or-60-degrees.gif\" alt=\"summary-how to do a bond rotation of 120 180 or 60 degrees\" width=\"640\" height=\"472\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Bond Rotation Basics: Interchanging Any 3 Groups On Carbon Performs A 120\u00b0 Bond Rotation<\/a><\/li>\n<li><a href=\"#two\">Bond Rotation Practice<\/a><\/li>\n<li><a href=\"#three\">120\u00b0 Rotations on Fischer Projections<\/a><\/li>\n<li><a href=\"#four\">180\u00b0 Rotations: Two Templates<\/a><\/li>\n<li><a href=\"#five\">Bond Rotation Practice (180\u00b0)<\/a><\/li>\n<li><a href=\"#six\">60\u00b0 Bond Rotations<\/a><\/li>\n<li><a href=\"#seven\">Multiple Bond Rotations<\/a><\/li>\n<li><a href=\"#eight\">Summary<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quiz\">Quiz Yourself!<\/a><\/li>\n<li><a href=\"#references\">(Advanced) References and Further Reading<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><a id=\"one\"><\/a>1. Bond Rotation Basics: 120\u00b0 Rotations<\/h2>\n<p>This article is to guide you through the times in your life when you need to draw a <strong>bond rotation.<\/strong><\/p>\n<figure id=\"attachment_35746\" aria-describedby=\"caption-attachment-35746\" style=\"width: 540px\" class=\"wp-caption alignnone\"><img decoding=\"async\" class=\"wp-image-35746\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/11\/1-Heinlein-quote-specialization-is-for-insects.png\" alt=\"Heinlein quote - specialization is for insects - bond rotation is important\" width=\"540\" height=\"334\" srcset=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/11\/1-Heinlein-quote-specialization-is-for-insects.png 1025w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/11\/1-Heinlein-quote-specialization-is-for-insects-300x186.png 300w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/11\/1-Heinlein-quote-specialization-is-for-insects-768x475.png 768w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/11\/1-Heinlein-quote-specialization-is-for-insects-760x470.png 760w\" sizes=\"(max-width: 540px) 100vw, 540px\" \/><\/a><figcaption id=\"caption-attachment-35746\" class=\"wp-caption-text\">Good ol&#8217; Robert Heinlein<\/figcaption><\/figure>\n<p>For most purposes, we are really only going to deal with the rotation of C-C bonds, but it can also apply to the rotation of other\u00a0<strong>sigma\u00a0<\/strong>bonds.<\/p>\n<p>We will just do rotation of C-C <strong>sigma<\/strong> bonds in simple <strong>chains<\/strong> here, since 1) bond rotation in small rings is restricted <span style=\"color: #800080;\">[<a style=\"color: #800080;\" href=\"https:\/\/www.masterorganicchemistry.com\/2014\/02\/18\/introduction-to-cycloalkanes-1\/\"><em>See Article: Introduction to Cycloalkanes<\/em><\/a>]<\/span> and 2) pi bonds cannot undergo free rotation.<\/p>\n<p>Furthermore, although bonds <em>can<\/em> be rotated to an infinitesimal degree, we generally only care about showing bond rotations in increments of<strong> 60 degrees.\u00a0 <\/strong>This makes 3-dimensional molecules easier to depict on a <strong>flat<\/strong> piece of paper (or screen) since <strong>two<\/strong> of the four groups attached to tetrahedral carbon can be drawn in the <strong>plane<\/strong> of the page.<\/p>\n<p>Since the carbon chain is drawn in the plane of the page 99% of the time, it follows from this we will focus on showing how to do rotations about <strong>one<\/strong> of the C-C bonds that is in the <strong>plane\u00a0<\/strong>of the page.<\/p>\n<p>Finally,\u00a0 I&#8217;m going to assume that you know that in our convention for drawing tetrahedral carbon,\u00a0 a <strong>wedged<\/strong> bond indicates that a group is pointing out of the page, while a\u00a0<strong>dashed<\/strong> bond indicates a group is going into the page. [<span style=\"color: #993366;\"><em>See article &#8211; <a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/03\/12\/common-mistakes-drawing-tetrahedral-carbons\/\">The Wedge Dash Convention for Drawing Tetrahedral Carbon<\/a><\/em><\/span>]<\/p>\n<p>Also, for our purposes, it&#8217;s most important whether a bond is a <strong>dash<\/strong> or <strong>wedge<\/strong>. Not whether it&#8217;s pointing left or right. There are always two different ways of depicting the dashed and wedged groups (one on the right, one on the left) and they are\u00a0<strong>equivalent<\/strong>. It&#8217;s just a matter of\u00a0<strong>perspective<\/strong> which one we choose to draw.<\/p>\n<p><img decoding=\"async\" src=\"https:\/\/media.giphy.com\/media\/v1.Y2lkPTc5MGI3NjExc2w3czBscnM5eWV6MjVzNnd3NnR2dzM5ZTljMmt5ZnNxM3dlY2xwdyZlcD12MV9pbnRlcm5hbF9naWZfYnlfaWQmY3Q9Zw\/h3rHx6AF0igvhSJMRC\/giphy.gif\" \/><\/p>\n<p>With that out of the way, here is the first thing to know about bond rotations.<\/p>\n<p><strong>If you interchange any three groups on a tetrahedral carbon you will have drawn a bond rotation<\/strong>.<\/p>\n<p>That&#8217;s it.<\/p>\n<ul>\n<li>You don&#8217;t have to think in 3-D.<\/li>\n<li>You are really just picking 3 symbols on a sheet of paper and interchanging them.<\/li>\n<li><em>You don&#8217;t have to even imagine you are doing a bond rotation.<\/em><\/li>\n<li>The net result will be a bond rotation of 120\u00b0, either clockwise or counterclockwise.<\/li>\n<\/ul>\n<p>Let&#8217;s illustrate. Here is an isomer of 2-bromobutane. Let&#8217;s do a rotation about the C-C bond that connects the chiral carbon (C) with the ethyl carbon (marked by the green circle).<\/p>\n<p>To do a bond rotation of 120\u00b0,<strong> all we need to do is interchange 3 groups:\u00a0<\/strong>Br, H, and CH<sub>3\u00a0<\/sub>while keeping the fourth group (CH<sub>2<\/sub>CH<sub>3<\/sub>) in the same place.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-35747\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/11\/3-a-bond-rotation-is-achieved-simplly-by-interconverting-any-3-groups.gif\" alt=\"a bond rotation is achieved simplly by interconverting any 3 groups\" width=\"640\" height=\"298\" \/><\/a><\/p>\n<p>Woot! That&#8217;s it!\u00a0 We&#8217;ve done a bond rotation of 120\u00b0 <strong>clockwise<\/strong> when viewed from the right.<\/p>\n<p>It translates to this:<\/p>\n<p><iframe class=\"giphy-embed\" src=\"https:\/\/giphy.com\/embed\/BptmbtPvzst5KYtkEA\" width=\"480\" height=\"270\" frameborder=\"0\" allowfullscreen=\"allowfullscreen\"><\/iframe><\/p>\n<p><a href=\"https:\/\/giphy.com\/gifs\/organicchemistry-stereochemistry-bondrotations-BptmbtPvzst5KYtkEA\">via GIPHY<\/a><\/p>\n<p>Alternatively, let&#8217;s start with the same molecule drawn slightly differently and do the same operation. <span style=\"color: #800080;\"><em>(Note that in this example that the chiral carbon ends up on the &#8220;bottom&#8221; of the zigzag carbon chain, so the H and Br are pointing down instead of up. Completely identical molecule to the one drawn above,\u00a0 but a slightly different representation).\u00a0<\/em><\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35748\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/11\/5-how-to-do-a-bond-rotation-with-three-groups-interchanged.gif\" alt=\"how to do a bond rotation with three groups interchanged\" width=\"640\" height=\"283\" \/><\/a><\/p>\n<p>In this case we&#8217;ve done a rotation of 120\u00b0 <strong>counter<\/strong>&#8211;<strong>clockwise<\/strong> (when viewed from the right) which is equivalent to a rotation of 240\u00b0 clockwise.<\/p>\n<p><span style=\"color: #800080;\"><em>(A key thing to notice is that the configuration of the chiral center does not change. It&#8217;s (S) on the left and also (S) on the right after bond rotation has occurred.)<\/em><\/span><\/p>\n<p>That&#8217;s equivalent to doing this:<\/p>\n<p><img decoding=\"async\" src=\"https:\/\/media.giphy.com\/media\/v1.Y2lkPTc5MGI3NjExbmgwOTZlNzRkNHVqb3A0OWhpcWhtaTFjbndhZjllOXhwZWpkb3gwYiZlcD12MV9pbnRlcm5hbF9naWZfYnlfaWQmY3Q9Zw\/VFLKBaw1quhBxpBFht\/giphy.gif\" \/><\/p>\n<p>In each case we have performed a rotation of 120\u00b0 or 240\u00b0.<\/p>\n<p><span style=\"color: #993366;\"><em>I will leave it as an exercise to the reader to prove that interchanging\u00a0<strong>any<\/strong> 3 groups on carbon leads to a bond rotation.\u00a0<\/em><\/span><\/p>\n<p>There&#8217;s just one extremely important thing to watch out for.<\/p>\n<p>Only\u00a0<strong>one<\/strong> group on the carbon should remain in its original position. The other three groups\u00a0<strong>must<\/strong> be exchanged!<\/p>\n<p>If you only exchange <strong>two<\/strong> groups, then you have not performed a bond rotation. Instead, you have <strong>inverted<\/strong> the configuration (i.e. you have broken some bonds).<\/p>\n<p>Switching two groups on a chiral center will invert the configuration from (<em>R<\/em>) to (S) and vice versa. While this is also a useful trick of its own accord (<span style=\"color: #993366;\">See article: <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2011\/01\/24\/how-to-draw-enantiomer\/\"><em>How to Draw the Enantiomer of A Chiral Molecule<\/em><\/a><\/span>) it&#8217;s\u00a0<strong>not\u00a0<\/strong>a bond rotation.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35749\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/11\/7-beware-that-just-flipping-two-groups-does-not-make-a-bond-rotation-it-inverts-configuration.gif\" alt=\"beware that just flipping two groups does not make a bond rotation it inverts configuration\" width=\"640\" height=\"216\" \/><\/a><\/p>\n<h2><a id=\"two\"><\/a>2. Bond Rotation Practice<\/h2>\n<p>Probably the most common instance of using a bond rotation comes up when determining the absolute configuration (<em>R\/S<\/em>) of a molecule and being faced with a #4 ranked substituent (generally H) that is either on a wedge or in the plane of the page.<\/p>\n<p>One way to put the #4 substituent in the back is to do a bond rotation. So let&#8217;s do two exercises in that vein.<\/p>\n<p>In this case, the hydrogen is in the front. Show what the molecule would look like when the H is in the back (i.e. on a dash).<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35755\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35755\"] {\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=\"35755\"] {\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=\"35755\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35755\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35755 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35755\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-c9gsg\" data-id=\"c9gsg\">\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\/2624-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\/2624-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<p>In the case below, the H is in the plane of the page. Do a bond rotation that would put it in the back.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35756\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35756\"] {\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=\"35756\"] {\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=\"35756\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35756\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35756 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35756\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-wm9c1\" data-id=\"wm9c1\">\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\/2625-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\/2625-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<p><em><span style=\"color: #993366;\">An alternative to doing a bond rotation is to learn to apply the Single Swap Rule, covered here &#8211; <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2011\/01\/24\/how-to-draw-enantiomer\/\">How To Draw The Enantiomer of a Chiral Molecule<\/a>.<\/span><\/em><\/p>\n<h2><a id=\"three\"><\/a>3. 120\u00b0 Rotations On Fischer Projections<\/h2>\n<p>The technique of exchanging any three groups also works when the molecule is drawn from alternative perspectives, such as in the Fischer and Newman projections.<\/p>\n<p>For instance, show how to do a bond rotation in this Fischer projection:<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35757\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35757\"] {\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=\"35757\"] {\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=\"35757\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35757\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35757 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35757\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-hefj9\" data-id=\"hefj9\">\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\/2626-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\/2626-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<p>It really is as straightforward as switching around three groups (<span style=\"color: #800080;\"><em>but not two!<\/em><\/span>)<\/p>\n<p>Do two bond rotations here. Does this reveal anything special about the molecule?<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35758\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35758\"] {\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=\"35758\"] {\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=\"35758\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35758\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35758 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35758\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-3r58v\" data-id=\"3r58v\">\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\/2627-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\/2627-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<p>From doing all the bond rotations it should reveal that the molecule is a meso compound.<\/p>\n<p>Doing bond rotations is\u00a0<em>one<\/em> way of determining whether a molecule is a meso compound or not. (<span style=\"color: #800080;\"><em>For more, see <a style=\"color: #800080;\" href=\"https:\/\/www.masterorganicchemistry.com\/2011\/01\/12\/the-meso-trap\/\">The Meso Trap &#8211; Identifying Meso Compounds<\/a>. )<\/em><\/span><\/p>\n<p><span style=\"color: #800080;\"><em>For an article on how to interchanging Newman projections via bond rotation, see <a style=\"color: #800080;\" href=\"https:\/\/www.masterorganicchemistry.com\/2020\/05\/29\/newman-projection-of-butane-and-gauche-conformation\/\">Newman Projection of Butane<\/a>, among others.\u00a0<\/em><\/span><\/p>\n<h2><a id=\"four\"><\/a>4. 180\u00b0 Rotations: Two Templates<\/h2>\n<p>Life would be simpler if all bond rotations were 120\u00b0 rotations.<\/p>\n<p>Alas, there are times when we absolutely must do an 180\u00b0 or 60\u00b0 bond rotation. They are <em>slightly<\/em> more involved than doing a 120 bond rotation, but not by a lot.<\/p>\n<p><span style=\"color: #993366;\"><em>The 180\u00b0 is arguably more important since it results in rotating the carbon chain, so we&#8217;ll cover that first.\u00a0<\/em><\/span><\/p>\n<p><strong>A good template to have by your side for these occasions is a simple tetrahedral carbon with 4 different colored atoms attached.\u00a0<\/strong><\/p>\n<p>Just by rotating the tetrahedral carbon you will go a long way towards being able to map these rotations out in your mind.<\/p>\n<p>If you don&#8217;t have a model kit handy, you can just use your fingers as a guide, even if it looks a bit like you are making gang symbols.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35750\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/11\/12-molecular-model-kit-or-hand.gif\" alt=\"if one does not have a molecular model kit it's possible to use one's hand instead\" width=\"640\" height=\"278\" \/><\/a><\/p>\n<p>Any line drawing of a tetrahedral carbon atom will have <strong>two<\/strong> groups bonded to carbon that are in the <strong>plane<\/strong> of the page. Since we like to make line drawings where everything is flat, those groups are usually carbon atoms,<\/p>\n<p>A 180\u00b0 rotation is useful because it results in a rotation of the carbon chain.<\/p>\n<p>There are really two key templates to examine for 180\u00b0 rotations, which I will arbitrarily call the starting point a &#8220;peak&#8221; or a &#8220;valley&#8221;.\u00a0 [<a href=\"#noteone\"><span style=\"color: #ff0000;\">Note 1<\/span><\/a> ]<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35751\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/11\/13-two-useful-templates-for-180-degree-rotation-of-bonds-the-peak-and-valley-templates.gif\" alt=\"two useful templates for 180 degree rotation of bonds - the peak and valley templates\" width=\"640\" height=\"212\" \/><\/a><\/p>\n<p>A 180\u00b0 bond rotation in the first template, starting from the &#8220;peak&#8221; looks like this:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35752\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/11\/14-how-to-do-a-180-bond-rotation-one-useful-model-mapping-out-all-groups.gif\" alt=\"how to do a 180 bond rotation - one useful model mapping out all groups\" width=\"640\" height=\"316\" \/><\/a><\/p>\n<p>If you map out the starting positions and the end positions,<\/p>\n<ul>\n<li>the group that is <strong>in the plane<\/strong> (pointing down)<strong> remains in the plane<\/strong>, pointing up.<\/li>\n<li>the <strong>wedged<\/strong> group (pointing up) becomes <strong>dashed<\/strong> (pointing down)<\/li>\n<li>the <strong>dashed<\/strong> group (pointing up) becomes <strong>wedged<\/strong> (pointing down)<em style=\"color: #993366;\">\u00a0<\/em><\/li>\n<\/ul>\n<p>In practice, this rotation looks like this:<\/p>\n<p><img decoding=\"async\" src=\"https:\/\/media.giphy.com\/media\/v1.Y2lkPTc5MGI3NjExYTQ3Mm5wYmNiYm10bHYxaHpjcnhoNHFtYnVsanZ3b2YxdDdzd3piaCZlcD12MV9pbnRlcm5hbF9naWZfYnlfaWQmY3Q9Zw\/xFL832OToggn4eZaGQ\/giphy.gif\" \/><\/p>\n<p>In the second template, we start with the valley (<span style=\"color: #800080;\"><em>i.e. from the bottom of the zigzag in the line diagram<\/em><\/span>).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35753\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/11\/16-how-to-do-a-180-bond-rotation-another-useful-model-mapping-out-all-groups.gif\" alt=\"how to do a 180 bond rotation - another useful model mapping out all groups\" width=\"640\" height=\"268\" \/><\/a><\/p>\n<p>Mapping out the starting and end positions here, we get:<\/p>\n<ul>\n<li>the group that is <strong>in the plane<\/strong> (pointing up) <strong>remains in the plane<\/strong>, pointing down<\/li>\n<li>the <strong>wedged<\/strong> group (pointing down) becomes <strong>dashed<\/strong> (pointing up)<\/li>\n<li>the <strong>dashed<\/strong> group (pointing down) becomes <strong>wedged<\/strong> (pointing up)<\/li>\n<\/ul>\n<p>This is what the rotation looks like with a model.<\/p>\n<p><img decoding=\"async\" src=\"https:\/\/media.giphy.com\/media\/v1.Y2lkPTc5MGI3NjExdXU0b3Zibzh0OTNvcm83N296aDJ6dHR3cGZ6bzFhcThyM3E5b2JzMyZlcD12MV9pbnRlcm5hbF9naWZfYnlfaWQmY3Q9Zw\/sChB0kVvZif0aVkxmY\/giphy.gif\" \/><\/p>\n<h2><a id=\"five\"><\/a>5. Bond Rotation Practice: 180\u00b0 Rotations<\/h2>\n<p>OK, now let&#8217;s try doing some 180\u00b0 bond rotations.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35759\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35759\"] {\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=\"35759\"] {\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=\"35759\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35759\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35759 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35759\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-zsxdx\" data-id=\"zsxdx\">\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\/2628-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\/2628-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<p>Here&#8217;s another one:<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35760\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35760\"] {\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=\"35760\"] {\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=\"35760\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35760\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35760 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35760\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-39k4p\" data-id=\"39k4p\">\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\/2629-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\/2629-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=\"six\"><\/a>6. 60\u00b0 Bond Rotations<\/h2>\n<p>Yes, we can also do 60\u00b0 bond rotations.<\/p>\n<p>There&#8217;s good news, though. If you can do a 180\u00b0,\u00a0 you can certainly do a 60\u00b0, since the 60\u00b0 follows a similar template.<\/p>\n<p>Here&#8217;s two templates, starting from a &#8220;peak&#8221; or a &#8220;valley&#8221; of the carbon chain:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35754\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/11\/20-how-to-do-a-60-degree-bond-rotation-template.gif\" alt=\"how to do a 60 degree bond rotation - template\" width=\"640\" height=\"231\" \/><\/a><\/p>\n<p>Here is an example of a 60\u00b0 rotation starting from the &#8220;peak&#8221;<\/p>\n<p><img decoding=\"async\" src=\"https:\/\/media.giphy.com\/media\/v1.Y2lkPTc5MGI3NjExNDgyc3A0cnR4Z3JtN3Nwems5YnZrbXVocTdoMGVzOHpkOTZtdzVtbSZlcD12MV9pbnRlcm5hbF9naWZfYnlfaWQmY3Q9Zw\/t1p0IuaFEFCrxNYWnY\/giphy.gif\" \/><\/p>\n<p>Here is am example of a 60\u00b0 rotation starting from the &#8220;valley&#8221;:<\/p>\n<p><img decoding=\"async\" src=\"https:\/\/media.giphy.com\/media\/v1.Y2lkPTc5MGI3NjExYTUwOXdsdDJkd205NzFwYjhoYXYxNXU2dzJjNnc4Y290Z3U1cWppdyZlcD12MV9pbnRlcm5hbF9naWZfYnlfaWQmY3Q9Zw\/Mh98HmohLmrmKiLIBU\/giphy.gif\" \/><\/p>\n<h2><a id=\"seven\"><\/a>7. Doing Multiple Bond Rotations<\/h2>\n<p>So far so good. We&#8217;ve shown how to do bond rotations along <strong>one<\/strong> carbon carbon bond. Slap yourself on the back if you&#8217;ve been successful at the exercises.<\/p>\n<p>As we know, however, life can inflict cruel punishments.\u00a0 What if we need to do multiple bond rotations?<\/p>\n<p><em>Yes<\/em>, we\u00a0<em>could<\/em> apply what we have learned above to do all those bond rotations.<\/p>\n<p><strong>But&#8230;.\u00a0<\/strong>one starts to run into a law of diminishing returns building models, applying templates,\u00a0 and all that jazz.<\/p>\n<p>So I present to you an alternate solution.<\/p>\n<p>If you have to show the result of multiple bond rotations about a carbon chain, my advice is to do the following:<\/p>\n<ul>\n<li>Number your carbons.<\/li>\n<li>Determine the absolute configuration (i.e. (R)\/(S)) of all chiral centers<\/li>\n<li>Redraw your carbon chain to the desired conformation<\/li>\n<li>Fill in all the substituents on the non-chiral carbons<\/li>\n<li>Put in all the substituents on the chiral carbons, and then determine (R)\/(S) on each. If any of them have the wrong value, swap the dashed and wedged groups to obtain the correct configuration.<\/li>\n<\/ul>\n<p>It may sound like a lot of work, but trust me, it&#8217;s less work than fudging around with models and everything else.<\/p>\n<h2><a id=\"eight\"><\/a>8. Summary<\/h2>\n<ul>\n<li>If there&#8217;s one key trick to get out of this article, I&#8217;d say it&#8217;s just learning that <strong>swapping any 3 groups about a carbon gives you the result of a bond rotation<\/strong>. This alone can make the task of determining R\/S when #4 is in the front or in the plane of the page significantly easier.<\/li>\n<li>Bond rotations should <strong>never<\/strong> result in changing the configuration about a carbon (i.e. going from (R) to (S) or vice-versa.\u00a0 One way to check if you&#8217;ve done a bond rotation correctly is to determine (R\/S) before and after your bond rotation.<\/li>\n<li>Make sure to swap <strong>3,\u00a0<\/strong>since swapping two will just flip the configuration.<\/li>\n<li>Doing 180\u00b0 bond rotations gets significantly easier with practice.\u00a0 I may suggest carrying around a single tetrahedral carbon from a model kit with 4 different substituents attached. It can come in handy for doing bond rotations and also for determining R\/S. If anyone asks you what it is, just tell them it&#8217;s a piece of avant-garde sculpture or something.<\/li>\n<li>If you don&#8217;t have a model kit, just using your hands can be enough. Never forget that molecules are just 3-dimensional objects like anything else.<\/li>\n<\/ul>\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\/2011\/01\/24\/how-to-draw-enantiomer\/\" class=\"\"><span>How To Draw The Enantiomer Of A Chiral Molecule<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/01\/12\/the-meso-trap\/\" class=\"\"><span>The Meso Trap<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/03\/12\/common-mistakes-drawing-tetrahedral-carbons\/\" class=\"\"><span>Wedge And Dash Convention For Tetrahedral Carbon<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/01\/17\/determining-rs-2-the-method-of-dots\/\" class=\"\"><span>Assigning Cahn-Ingold-Prelog (CIP) Priorities (2) \u2013 The Method of Dots<\/span><\/a><\/li><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\/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\/2016\/10\/20\/introduction-to-assigning-r-and-s-the-cahn-ingold-prelog-rules\/\" class=\"\"><span>Introduction to Assigning (R) and (S): The Cahn-Ingold-Prelog Rules<\/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\/2020\/03\/27\/conformational-isomers-of-propane\/\" class=\"\"><span>Conformational Isomers of Propane<\/span><\/a><\/li><\/ul><\/div>\n<p><strong><a id=\"noteone\"><\/a>Note 1.\u00a0<\/strong>Only two templates, but four if you consider their mirror images where we are looking from right to left along the carbon-carbon bond. For simplicity we&#8217;re just going to omit those cases.<\/p>\n<hr \/>\n<h2><strong><a id=\"quiz\"><\/a>Quiz Yourself!<\/strong><\/h2>\n<p>[90\u00b0 rotation]<\/p>\n<hr \/>\n<h2><strong><a id=\"references\"><\/a>(Advanced) References and Further Reading<\/strong><\/h2>\n<p>References<\/p>\n","protected":false},"excerpt":{"rendered":"<p>How To Draw A Bond Rotation Rotation can happen to an infinitesimal extent around carbon-carbon single bonds but for the most part we only really <\/p>\n","protected":false},"author":1,"featured_media":35767,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1413],"tags":[14872,14873,642,1404,273],"post_folder":[],"class_list":["post-26151","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-stereochemistry-chirality","tag-bond-rotation","tag-dash-wedge","tag-fischer-projection","tag-meso-compounds","tag-stereochemistry"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>How To Draw A Bond Rotation &#8211; 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