{"id":1292,"date":"2011-01-24T17:39:19","date_gmt":"2011-01-24T23:39:19","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=1292"},"modified":"2026-04-19T04:23:10","modified_gmt":"2026-04-19T09:23:10","slug":"how-to-draw-enantiomer","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2011\/01\/24\/how-to-draw-enantiomer\/","title":{"rendered":"How To Draw The Enantiomer Of A Chiral Molecule"},"content":{"rendered":"<p><strong>How To Draw The Enantiomer Of A Compound &#8211; The Single Swap Rule<\/strong><\/p>\n<ul>\n<li>Exchanging any two groups on a chiral center will flip the R\/S designation from <em>R<\/em> to <em>S<\/em> or vice versa. (<span style=\"color: #993366;\"><em>A subsequent flip of two groups will give you back the original configuration<\/em><\/span>). This is sometimes referred to as the &#8220;<strong>single swap rule<\/strong>&#8220;.<\/li>\n<li>For a chiral molecule with only <strong>one<\/strong> chiral center, a <strong>single swap<\/strong> on that chiral center will convert it into its <strong>enantiomer<\/strong><\/li>\n<li>To draw the enantiomer of a chiral molecule, 1) identify all the chiral centers and 2) do a single swap on each chiral center <em>(<span style=\"color: #993366;\">Note &#8211; it&#8217;s equivalent to just convert all wedged bonds to dashed bonds and vice versa<\/span>)<\/em><\/li>\n<li>The single swap rule is also useful for determining R\/S in cases where the #4 priority group points out of the page (&#8220;wedged&#8221;). First, do a single swap such that the #4 group is dashed. Then, determine <em>R\/S<\/em> normally. Since a single swap was performed, whatever value you get will be the opposite of the true configuration.\u00a0 (<span style=\"color: #993366;\"><em>With enough practice you will just do this in your head<\/em><\/span>)<\/li>\n<li>This trick also works for when the #4 group is in the plane of the page. Just swap the #4 group (in the plane) with whichever group is dashed, then determine <em>R\/S<\/em> normally. Whatever value you get will also be the opposite.<\/li>\n<li>To draw the diastereomer of a molecule, do a single swap on at\u00a0<em>least one <\/em>but <em>not all<\/em> chiral centers.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-35144\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2011\/01\/0-how-to-draw-the-enantiomer-of-a-chiral-compound-summary-single-swap-rule.gif\" alt=\"how to draw the enantiomer of a chiral compound summary single swap rule\" width=\"640\" height=\"707\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">The Single Swap Rule<\/a><\/li>\n<li><a href=\"#two\">Switching Any Two Groups Interconverts (R\/S) (It doesn&#8217;t matter which two!)<\/a><\/li>\n<li><a href=\"#three\">One Swap Gives Inversion of Configuration. Two Swaps Gives Retention<\/a><\/li>\n<li><a href=\"#four\">Two Ways To Draw The Enantiomer Of A Molecule With 1 Chiral Center<\/a><\/li>\n<li><a href=\"#five\">Drawing The Enantiomer Of A Molecule With 2 or More Chiral Centers<\/a><\/li>\n<li><a href=\"#six\">Just Watch Out For Meso Compounds<\/a><\/li>\n<li><a href=\"#seven\">Applications of The Single Swap Rule &#8211; Determining R\/S When #4 Group Is In The Front<\/a><\/li>\n<li><a href=\"#eight\">Applications of The Single Swap Rule (2) &#8211; Determining R\/S When #4 Group Is In The Plane of The Page<\/a><\/li>\n<li><a href=\"#nine\">Drawing Diastereomers<\/a><\/li>\n<li><a href=\"#ten\">Flipping 3 Groups Gives A Bond Rotation<\/a><\/li>\n<li><a href=\"#eleven\">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. The Single Swap Rule<\/h2>\n<p>Here&#8217;s a neat trick.<\/p>\n<ul>\n<li>Swapping <strong>any two groups <\/strong>on an asymmetric (&#8220;chiral&#8221;) carbon atom transforms the configuration around carbon to its <strong>mirror image<\/strong>.<\/li>\n<li>For a molecule with a <strong>single<\/strong> chiral center, this means that doing a single swap on that chiral center will result in the <strong>enantiomer<\/strong>.<\/li>\n<li>A\u00a0<strong>second\u00a0<\/strong>swap of two groups will restore the original configuration.<\/li>\n<\/ul>\n<p>A nice description of this principle (<span style=\"color: #993366;\"><em>not my invention<\/em><\/span>) is to call it the &#8220;single swap rule&#8221;<\/p>\n<p><iframe class=\"giphy-embed\" src=\"https:\/\/giphy.com\/embed\/1cvVnCRxxq152L3uw6\" width=\"480\" height=\"270\" frameborder=\"0\" allowfullscreen=\"allowfullscreen\"><\/iframe><\/p>\n<p><a href=\"https:\/\/giphy.com\/gifs\/1cvVnCRxxq152L3uw6\">via GIPHY<\/a><\/p>\n<p>&nbsp;<\/p>\n<p>For chemistry purposes, two molecules that are <strong>superimposable<\/strong> will have identical chemical and physical properties and are considered to be <strong>identical<\/strong> molecules.<\/p>\n<p>Two molecules that are <strong>non-superimposable<\/strong> [<a href=\"#noteone\"><span style=\"color: #ff0000;\">Note 1<\/span><\/a> ] are <strong>not <\/strong>identical and will have at least some differences in their physical and chemical properties (<span style=\"color: #993366;\"><em>like melting points, boiling points, solubility properties, and more<\/em><\/span>)<\/p>\n<p>The special case where two <strong>non-superimposable<\/strong> molecules are also <strong>mirror images<\/strong> is called\u00a0<strong>optical isomerism\u00a0<\/strong>and the two molecules are referred to as\u00a0<strong>enantiomers<\/strong>. [<span style=\"color: #993366;\"><em>See article: <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2018\/09\/10\/types-of-isomers\/\">Types of Isomers<\/a><\/em><\/span>]<\/p>\n<p>Enantiomers have identical physical properties except for the direction in which they rotate plane-polarized light. [<span style=\"color: #993366;\"><em>See article: <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2017\/02\/07\/optical-rotation-optical-activity-and-specific-rotation\/\">Optical Rotation, Optical Activity and Specific Rotation<\/a><\/em><\/span>]<\/p>\n<p>Optical isomerism is most commonly encountered in the case of molecules containing a carbon attached to four different groups (an asymmetric carbon center or &#8220;chiral carbon&#8221;) . [<span style=\"color: #ff0000;\"><a href=\"#notetwo\"><span style=\"color: #ff0000;\">Note 2<\/span><\/a><\/span>]<\/p>\n<h2><a id=\"two\"><\/a>2. Yes, Really &#8211; Switch Any Two Groups &#8211; (It doesn&#8217;t matter which two)<\/h2>\n<p>If you do the math, a tetrahedral carbon with 4 different substituents will have <strong>six<\/strong> possible ways to swap two groups.<\/p>\n<p>Are they all\u00a0<em>really<\/em> equivalent?<\/p>\n<p>Yes! You can verify this yourself by using a model kit. Starting with two identical molecules, swap any two groups and see what happens. You should find that you have created the enantiomer.<\/p>\n<p>Alternatively&#8230;. here is a video of flipping all 6, so you don&#8217;t have to do it<\/p>\n<p><iframe class=\"giphy-embed\" src=\"https:\/\/giphy.com\/embed\/U8YQzuTRT5ptaSzm66\" width=\"480\" height=\"270\" frameborder=\"0\" allowfullscreen=\"allowfullscreen\"><\/iframe><\/p>\n<p><a href=\"https:\/\/giphy.com\/gifs\/stereochemistry-U8YQzuTRT5ptaSzm66\">via GIPHY<\/a><\/p>\n<p>&nbsp;<\/p>\n<h2><a id=\"three\"><\/a>3. Doing a single swap inverts R\/S.<\/h2>\n<p>You may recall that one way to distinguish enantiomers is that they have the same connectivity but opposite (<em>R\/S<\/em>) values.<\/p>\n<p>For example the enantiomer of <em>(R)-<\/em>AwesomeMoleculene<strong>\u00a0<\/strong>will naturally be (<em>S<\/em>)-AwesomeMoleculene<\/p>\n<p>Since doing a single swap converts a chiral molecule with one asymmetric carbon to its <strong>enantiomer<\/strong>, it is also true is that doing a <strong>single swap\u00a0<\/strong>on a chiral carbon will flip the configuration of that carbon from (<em>R<\/em>) to (<em>S<\/em>)\u00a0 (<span style=\"color: #993366;\"><em>or from S to R<\/em><\/span>).<\/p>\n<p>[<span style=\"color: #993366;\"><em>For more on (R) and (S) see this article on <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2016\/10\/20\/introduction-to-assigning-r-and-s-the-cahn-ingold-prelog-rules\/\">The Cahn-Ingold-Prelog Rules<\/a> (CIP).<\/em>] Briefly, the four atoms directly attached to the chiral carbon are assigned <strong>priorities<\/strong> 1-2-3-4 based on atomic weight (with rules for breaking ties,\u00a0 if necessary). Then with the #4 substituent in the <strong>back<\/strong>, we trace the path of the 1-2-3 substituents to see if they follow a <strong>clockwise<\/strong> (<em>R<\/em>) or <strong>counterclockwise<\/strong> (<em>S<\/em>) direction.<\/span>]<\/p>\n<p>Let&#8217;s say for the molecule in the videos above, these 4 atoms have priorities<\/p>\n<ul>\n<li>B = 1,<\/li>\n<li>G = 2,<\/li>\n<li>R = 3,<\/li>\n<li>W = 4<\/li>\n<\/ul>\n<p><span style=\"color: #993366;\"><em>(I&#8217;ve done this based on alphabetical order, but we could assign B = bromine G = chlorine R = fluorine and W = hydrogen if we want to)\u00a0<\/em><\/span><\/p>\n<p>Our starting molecule has the (<em>R<\/em>) configuration. Flipping any two groups (e.g. blue and red) gives the <strong>enantiomer<\/strong>, which has the (<em>S<\/em>) configuration.<\/p>\n<p>[<span style=\"color: #993366;\"><em>Note that in this example we are\u00a0<strong>only<\/strong>\u00a0exchanging the groups and otherwise <strong>leaving the bonds alone<\/strong> &#8211;\u00a0 much like what one would do when plucking atoms off a model kit and reattaching in a different order.\u00a0 There&#8217;s a second way to do a single swap where the groups are left alone and the dashed\/wedged bonds are swapped that we will discuss shortly<\/em><\/span>]<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-35120\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/06\/3-the-single-swap-rule-states-that-swapping-the-position-of-any-two-groups-will-result-in-flipping-the-configuration-from-R-to-S-or-vice-versa.gif\" alt=\"the single swap rule states that swapping the position of any two groups will result in flipping the configuration from R to S or vice versa\" width=\"640\" height=\"374\" \/><\/a><\/p>\n<p>A second swap (e.g. of blue and green) gives the <strong>enantiomer<\/strong> of (<em>S<\/em>), which now has the (<em>R<\/em>) configuration &#8211; the configuration of our original molecule!<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-35121\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/06\/4-single-swap-rule-two-successive-single-swaps-results-in-retention-of-configuration-about-a-chiral-center.gif\" alt=\"single swap rule - two successive single swaps results in retention of configuration about a chiral center\" width=\"640\" height=\"335\" \/><\/a><\/p>\n<p>So every time we do a single swap we toggle between <em>(S)<\/em> and <em>(R) &#8211;\u00a0<\/em>an\u00a0<em>inversion\u00a0<\/em>of configuration.<\/p>\n<p>It <strong>doesn&#8217;t matter<\/strong> which two groups you pick, you will get the same result.<\/p>\n<p>Two single swaps will lead to <em>retention<\/em> of configuration.<\/p>\n<h2><a id=\"four\"><\/a>4. How To Draw The Enantiomer Of Any Molecule With A Single Chiral Center (Two Ways)<\/h2>\n<p>All right. Let&#8217;s say we have a chiral molecule with a single chiral center and we are asked to draw the enantiomer.<\/p>\n<p>How would we do that?<\/p>\n<p>When you just have a single chiral center and a linear molecule, it&#8217;s pretty straightforward &#8211; even if the molecule is drawn in a Newman, Fischer or sawhorse projection. Here&#8217;s how.<\/p>\n<p>While keeping the <strong>bonds<\/strong> from the asymmetric carbon constant (<span style=\"color: #993366;\"><em>i.e. don&#8217;t move the bonds, don&#8217;t convert wedges to dashes or vice-versa, etc.<\/em><\/span>)\u00a0 all we have to do is <strong>swap<\/strong> the position of <strong>two groups<\/strong>. Just like you would when interconverting two groups on a model kit.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35134\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35134\"] {\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=\"35134\"] {\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=\"35134\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35134\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35134 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35134\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-07ds1\" data-id=\"07ds1\">\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\/2517-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\/2517-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>This can work pretty well. However,\u00a0 there are some situations where swapping the position of two groups will give ridiculous-looking results, especially when we have chiral centers that are part of a ring &#8211; <a href=\"\" class=\"custom-tooltip\" data-image=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/06\/Supp-1-Swapping-out-two-atoms-when-one-of-the-atoms-is-in-a-ring-can-lead-to-very-messy-looking-structures.gif\" data-link=\"\" data-title=\"\" data-text=\"\">hover here<\/a> or click the <a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/06\/Supp-1-Swapping-out-two-atoms-when-one-of-the-atoms-is-in-a-ring-can-lead-to-very-messy-looking-structures.gif\">link<\/a>.<\/p>\n<p>Thankfully there is a second,\u00a0 equivalent method of doing a single swap that works even better for most cases.<\/p>\n<p>The second method of doing a single swap is to <strong>keep all groups in the same place<\/strong>, and then\u00a0<strong>swap a wedged bond with a dashed bond. <\/strong><\/p>\n<p>Like this:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35122\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/06\/6-interconverting-a-wedge-and-a-dash-results-in-flipping-a-chiral-center-from-r-to-s-or-vice-versa.gif\" alt=\"interconverting a wedge and a dash results in flipping a chiral center from r to s or vice versa\" width=\"640\" height=\"361\" \/><\/a><\/p>\n<p>Note that we didn&#8217;t &#8220;move&#8221; the position of the atoms, we just interconverted which bond was wedged and which was dashed. But it still results in flipping (<em>R<\/em>) to (<em>S<\/em>) !<\/p>\n<p>There are many times when you will encounter an asymmetric carbon atom drawn such that only <strong>one<\/strong> group is drawn as a dash or a wedge.<\/p>\n<p>This is often the case when the chiral carbon has an implied (&#8220;hidden&#8221;) hydrogen\u00a0 <a href=\"\" class=\"custom-tooltip\" data-image=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/06\/Supp-2-One-example-of-where-a-molecule-is-drawn-having-a-single-wedged-or-dashed-bond-is-with-implicit-hydrogens.gif\" data-link=\"\" data-title=\"\" data-text=\"\">hover here<\/a> (<a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/06\/Supp-2-One-example-of-where-a-molecule-is-drawn-having-a-single-wedged-or-dashed-bond-is-with-implicit-hydrogens.gif\">link<\/a>) or when specifying the stereochemistry of just one group is sufficient to determine (<em>R\/S<\/em>)\u00a0<a href=\"\" class=\"custom-tooltip\" data-image=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/06\/Supp-3-Another-example-of-chiral-molecules-with-a-single-wedge-dash-is-found-where-an-extra-wedge-dash-would-be-superfluous.gif\" data-link=\"\" data-title=\"\" data-text=\"\">hover here<\/a> (<a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/06\/Supp-3-Another-example-of-chiral-molecules-with-a-single-wedge-dash-is-found-where-an-extra-wedge-dash-would-be-superfluous.gif\">link<\/a>).<\/p>\n<p>In these cases, just toggle that one bond between wedge\/dash\u00a0 and you will have performed a single swap.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35123\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/06\/7-cases-where-there-is-only-one-dash-or-one-wedge-include-the-case-where-there-is-an-implicit-hydrogen-or-a-second-dash-wedge-would-be-superfluous.gif\" alt=\"cases where there is only one dash or one wedge include the case where there is an implicit hydrogen or a second dash-wedge would be superfluous\" width=\"640\" height=\"421\" \/><\/a><\/p>\n<p>Here are some exercises on drawing enantiomers using the single swap principle:<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35135\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35135\"] {\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=\"35135\"] {\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=\"35135\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35135\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35135 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35135\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-r1rw2\" data-id=\"r1rw2\">\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\/2518-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\/2518-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=\"five\"><\/a>5. Drawing The Enantiomer Of Molecules With 2 Or More Chiral Centers<\/h2>\n<p>What if a molecule has more than one chiral center? Does this still work for drawing enantiomers? Yes! <span style=\"color: #993366;\">*<\/span><\/p>\n<p><span style=\"color: #993366;\"><em>(* see section 6)<\/em><\/span><\/p>\n<p>Here is (2<em>R, 3R)<\/em> tartaric acid. How would you draw the enantiomer?<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35136\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35136\"] {\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=\"35136\"] {\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=\"35136\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35136\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35136 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35136\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-vprxr\" data-id=\"vprxr\">\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\/2519-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\/2519-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>If you said, &#8220;just make all the wedges into dashes, and all the dashes into wedges&#8221;, then good job. This is sufficient to convert the molecule into its enantiomer.<\/p>\n<p>Now that you&#8217;ve done that, draw the enantiomers of these molecules each with two chiral centers\u00a0 (some of which you may have heard of).<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35137\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35137\"] {\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=\"35137\"] {\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=\"35137\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35137\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35137 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35137\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-bc1z5\" data-id=\"bc1z5\">\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\/2520-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\/2520-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>Let&#8217;s stretch it out a bit.\u00a0 What if our molecule has three (or even four!) chiral centers?<\/p>\n<p>Still works! Just find the chiral centers and do single swaps on each:<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35138\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35138\"] {\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=\"35138\"] {\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=\"35138\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35138\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35138 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35138\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-1goh2\" data-id=\"1goh2\">\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\/2521-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\/2521-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>Let&#8217;s get even more ambitious. Here are two famous molecules with multiple chiral centers. See if you can draw their enantiomers.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35139\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35139\"] {\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=\"35139\"] {\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=\"35139\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35139\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35139 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35139\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-50aby\" data-id=\"50aby\">\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\/2522-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\/2522-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>Note that once your molecule reaches a certain size, interconverting dashes and wedges becomes\u00a0<strong>much more convenient\u00a0<\/strong>than moving atoms around.<\/p>\n<h2><a id=\"six\"><\/a>6. Just Watch Out For Meso Compounds<\/h2>\n<p>Now that we&#8217;re feeling confident, let&#8217;s try another fun example.<\/p>\n<p>Convert (2<em>R<\/em>, 3<em>S<\/em>) tartaric acid to its mirror image by doing two single swaps.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35140\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35140\"] {\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=\"35140\"] {\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=\"35140\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35140\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35140 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35140\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-s10ie\" data-id=\"s10ie\">\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\/2523-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\/2523-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>Sure enough, this gives us (2<em>S<\/em>, 3<em>R<\/em>) tartaric acid.<\/p>\n<p>But is this the enantiomer? <strong>No<\/strong>!<\/p>\n<p>Why not?\u00a0 Because (<em>R,S<\/em>) tartaric acid is a<strong> meso compound<\/strong> &#8211; a molecule with chiral centers that contains an internal mirror plane. It&#8217;s an achiral molecule. (<span style=\"color: #993366;\"><em>See article &#8211; <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2011\/01\/12\/the-meso-trap\/\">Meso Compounds<\/a><\/em><\/span>)<\/p>\n<p><span style=\"color: #993366;\"><em>(This is easier to see once you do a bond rotation to reveal the mirror plane.)<\/em><\/span><\/p>\n<p>So the &#8220;single swap rule&#8221; has a catch. Flipping all the chiral centers will only result in the enantiomer if the compound is chiral.<\/p>\n<p>If you flip <strong>all<\/strong> the chiral centers on a meso compound, you&#8217;ll still have an achiral compound.<\/p>\n<h2><a id=\"seven\"><\/a>7. Using the single swap rule for determining R\/S when #4 is not in front.<\/h2>\n<p>The single swap rule is also helpful for determining <em>R\/S<\/em>.<\/p>\n<p>As mentioned above, R\/S is determined by placing the priority #4 substituent in the <strong>back<\/strong> and then tracing the path of the 1-2-3 substituents.<\/p>\n<p>(<span style=\"color: #993366;\"><em>See article &#8211; <a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/10\/20\/introduction-to-assigning-r-and-s-the-cahn-ingold-prelog-rules\/\">Introduction to Assigning (R) and (S) &#8211; the Cahn Ingold Prelog Priority Rules<\/a><\/em><\/span>).<\/p>\n<p>The trouble is that we will often encounter situations where\u00a0 #4 isn&#8217;t always helpfully drawn in the back (i.e. as a &#8220;dash&#8221;).<\/p>\n<p>One way to solve this is to get out your model kit, build the molecule and then rotate it around so that #4 is in the back.<\/p>\n<p>You know, like in this molecule.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35124\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/06\/15-example-of-trying-to-determine-r-s-when-the-fourth-ranked-substituent-is-in-the-front.gif\" alt=\"example of trying to determine r s when the fourth ranked substituent is in the front\" width=\"640\" height=\"161\" \/><\/a><\/p>\n<p>As one of my students once said, &#8220;<em>when I hear my instructor say &#8220;make a model&#8221; it&#8217;s like hearing my mom say, &#8220;clean your room<\/em>&#8220;.<\/p>\n<p><iframe class=\"giphy-embed\" src=\"https:\/\/giphy.com\/embed\/dK11O2DtdRx01k8ivK\" width=\"480\" height=\"248\" frameborder=\"0\" allowfullscreen=\"allowfullscreen\"><\/iframe><\/p>\n<p><a href=\"https:\/\/giphy.com\/gifs\/stereochemistry-dK11O2DtdRx01k8ivK\">via GIPHY<\/a><\/p>\n<p>&nbsp;<\/p>\n<p>OK, OK! You don&#8217;t\u00a0<em>need<\/em> to make a model.<\/p>\n<p>Single swap rule to the rescue!<\/p>\n<p>Just flip the #4 priority group with the group that is a dash. When you do this, you will flip <em>R<\/em> to <em>S<\/em> (or vice versa).<\/p>\n<p>Now you can determine <em>R\/S\u00a0<\/em>like you normally would.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35125\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/06\/17-example-of-using-the-single-swap-rule-to-determine-r-s-when-the-number-4-ranked-substituent-is-in-the-front.gif\" alt=\"-example of using the single swap rule to determine r s when the number 4 ranked substituent is in the front\" width=\"640\" height=\"568\" \/><\/a><\/p>\n<p>The thing is, whatever absolute configuration you get (<em>R<\/em> or\u00a0<em>S<\/em>), the\u00a0<strong>true<\/strong><strong> configuration will be the opposite since you previously did a single swap.\u00a0<\/strong><\/p>\n<p>Knowing this, just &#8220;flip&#8221; the value you got to the opposite, and you&#8217;ll have the\u00a0<strong>true<\/strong> absolute configuration.<\/p>\n<p>Note that although I&#8217;ve drawn this entire process out, I think you&#8217;ll find that with a little bit of practice, you&#8217;ll just end up <strong>doing this in your head\u00a0<\/strong>when you see that the hydrogen (or whatever other #4 priority group you encounter) is pointing out of the page.<\/p>\n<p>It&#8217;s a very useful trick.<\/p>\n<h2><a id=\"eight\"><\/a>8. Using The Single Swap Rule When #4 Is In The Plane of the Page<\/h2>\n<p>This trick also works when the #4 group is in the <strong>plane<\/strong> of the page.<\/p>\n<p>As before, just do a <strong>single swap<\/strong> to put the group in the back. Then determine <em>R\/S<\/em>.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35126\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/06\/18-example-of-determining-r-s-when-the-number-4-substituent-is-in-the-plane-of-the-page.gif\" alt=\"example of determining r s when the number 4 substituent is in the plane of the page\" width=\"640\" height=\"488\" \/><\/a><\/p>\n<p>Whatever value of\u00a0<em>R\/S<\/em> you obtain will the the\u00a0<strong>opposite\u00a0<\/strong>of the &#8220;true&#8221; absolute configuration. So toggle the\u00a0<em>R\/S<\/em> value to get the true absolute configuration.<\/p>\n<h2><a id=\"nine\"><\/a>9. Drawing Diastereomers<\/h2>\n<p>The single swap rule is also useful for drawing <strong>diastereomers<\/strong>.<\/p>\n<p>Recall that diastereomers are stereoisomers that aren&#8217;t enantiomers. (<span style=\"color: #993366;\"><em>See article &#8211; <span style=\"color: #993366;\"><a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2018\/09\/10\/types-of-isomers\/\">Types of Isomers<\/a><\/span><\/em><\/span>)<\/p>\n<p>Since not\u00a0<strong>all<\/strong> chiral centers have to have opposite values from each other, finding a diastereomer of a given molecule isn&#8217;t too difficult.<\/p>\n<p>For example, a molecule with 5 chiral centers will have 2<sup>5<\/sup> possible stereoisomers (32).<\/p>\n<p>Testosterone (below) represents one of those 32 possibilities. Its enantiomer is another.<\/p>\n<p>The other 30 possibilities are all diastereomers of testosterone.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35127\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/06\/19-how-to-draw-the-diastereomer-of-a-molecule-with-multiple-chiral-centers-just-flip-at-least-one-but-not-all-chiral-centers.gif\" alt=\"how to draw the diastereomer of a molecule with multiple chiral centers - just flip at least one but not all chiral centers\" width=\"640\" height=\"369\" \/><\/a><\/p>\n<p>So to draw a diastereomer of a molecule you just need to draw a stereoisomer that isn&#8217;t an enantiomer.<\/p>\n<ul>\n<li>That means that for a molecule with <strong>N<\/strong> chiral centers, do <strong>at least 1<\/strong> but <strong>less<\/strong> <strong>than<\/strong> <strong>N<\/strong> single swaps.<\/li>\n<li>Alternatively, flip a double bond from (<em>E<\/em>) to (<em>Z<\/em>)<\/li>\n<\/ul>\n<h2><a id=\"ten\"><\/a>10. Flipping 3 is a bond rotation<\/h2>\n<p>When doing a single swap, make sure you stop at interconverting just two groups.<\/p>\n<p>Why?<\/p>\n<p>In the example below, <strong>three\u00a0<\/strong>groups have been interchanged. What happens to the absolute configuration (R\/S) ?<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35141\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35141\"] {\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=\"35141\"] {\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=\"35141\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35141\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35141 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35141\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-vvanl\" data-id=\"vvanl\">\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\/2524-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\/2524-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>That&#8217;s right. Interchanging 3 groups results in a <strong>bond rotation<\/strong>. I&#8217;ll have more to say about that in a future post.<\/p>\n<h2><strong><a id=\"eleven\"><\/a>11. Summary<\/strong><\/h2>\n<ul>\n<li>Swapping any two groups on an asymmetric carbon will flip its configuration from (R) to (S) or vice versa<\/li>\n<li>A second swap will result in retention of configuration<\/li>\n<li>For a chiral molecule with a single chiral center, this means that performing a single swap will result in its enantiomer.<\/li>\n<li>An alternative way to perform a single swap is to interchange a wedged and dashed bond on a chiral carbon.<\/li>\n<li>To draw the enantiomer of a molecule with two or more chiral centers, swap dashed\/wedged bonds on all chiral carbons. Just watch out for meso compounds (which are achiral and don&#8217;t have an enantiomer).<\/li>\n<li>To determine (R\/S) on a molecule where the #4 priority substituent is in the front (or in the plane of the page!) , perform a single swap to put the #4 group in the back. Then determine (R\/S). The true absolute configuration will be the opposite of this value.<\/li>\n<li>Interchanging 3 groups results in a bond rotation (with retention of absolute configuration!)<\/li>\n<\/ul>\n<hr \/>\n<h2><strong><a id=\"notes\"><\/a>Notes<\/strong><\/h2>\n<p><strong><a id=\"noteone\"><\/a>Note 1<\/strong> &#8211; Determining whether two molecules are superimposable also implies a certain time frame. For example, it&#8217;s possible for a molecule to have two\u00a0<strong>conformations\u00a0<\/strong>which are non-superimposable mirror images of each other. However, if these two conformers interconvert on a fast-enough time frame, then any effects of these enantiomeric conformers &#8211; such as equal and opposite optical rotation &#8211; will be cancelled out.<\/p>\n<p>One fairly arbitrary (but practical!) test is, &#8220;Can you store the two enantiomers in separate bottles without them interconverting&#8221;. Certain conformers with hindered rotation &#8211; known as\u00a0<strong>atropisomers<\/strong> &#8211; fit this description. One can purchase the enantiomers of 2-binaphthol.<\/p>\n<p><strong><a id=\"notetwo\"><\/a>Note 2<\/strong> &#8211; Other forms of chirality exist besides the situation where there are four different groups on tetrahedral carbon. Another prominent example often encountered in undergraduate organic chemistry is molecules that include an axis of chirality, such as certain substituted allenes. [<span style=\"color: #993366;\"><em>See article &#8211; <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2015\/01\/13\/chiral-allenes-and-chiral-axes\/\">Chiral Allenes and Chiral Axes<\/a><\/em><\/span>]<\/p>\n<p>&nbsp;<\/p>\n<hr \/>\n<h2><strong><a id=\"quiz\"><\/a>Quiz Yourself!<\/strong><\/h2>\n<p>&nbsp;<\/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\/3606-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\/0870-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\/0871-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\/0872-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\/0913-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\/2525-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\/2526-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\/2527-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<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 The Enantiomer Of A Compound &#8211; The Single Swap Rule Exchanging any two groups on a chiral center will flip the R\/S <\/p>\n","protected":false},"author":1,"featured_media":35144,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1413],"tags":[197,330,202,635,269,637,636,286,351],"post_folder":[],"class_list":["post-1292","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-stereochemistry-chirality","tag-diastereomers","tag-drawing","tag-enantiomers","tag-rs","tag-shortcuts","tag-single-swap","tag-stereocenters","tag-tips-2","tag-tricks"],"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 The Enantiomer Of A Chiral Molecule &#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\/01\/24\/how-to-draw-enantiomer\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"How To Draw The Enantiomer Of A Chiral Molecule &#8211; 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