{"id":10198,"date":"2016-10-20T15:22:21","date_gmt":"2016-10-20T19:22:21","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=10198"},"modified":"2026-04-17T21:06:05","modified_gmt":"2026-04-18T02:06:05","slug":"introduction-to-assigning-r-and-s-the-cahn-ingold-prelog-rules","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2016\/10\/20\/introduction-to-assigning-r-and-s-the-cahn-ingold-prelog-rules\/","title":{"rendered":"Introduction to Assigning (R) and (S): The Cahn-Ingold-Prelog Rules"},"content":{"rendered":"<p><strong>Assigning\u00a0<em>R<\/em> and\u00a0<em>S<\/em> Configurations With the Cahn-Ingold-Prelog (CIP) Rules<\/strong><\/p>\n<ul>\n<li>Enantiomers are stereoisomers that are <strong>non-superimposable<\/strong> mirror images of each other <span style=\"color: #993366;\"><em>(by the way, molecules that are superimposable mirror images of each other are considered to be <strong>identical<\/strong> molecules).\u00a0<\/em><\/span><\/li>\n<li>Enantiomers rotate plane-polarized light in equal and opposite directions, but there is no straightforward way to trace back the absolute configuration of a molecule to the direction of optical rotation<\/li>\n<li>A tetrahedral atom with four different substituents (a chiral center) can have <strong>two<\/strong> different configurations. A naming scheme developed by Cahn, Ingold and Prelog (CIP) is used for assigning the terms\u00a0 <em>R<\/em> or\u00a0<em>S\u00a0<\/em>to each chiral center.\u00a0<span style=\"color: #993366;\"><em> (When all the (R,S) designations of a molecule are specified, this is referred to as its &#8220;<strong>absolute<\/strong> configuration&#8221;.)<\/em><\/span><\/li>\n<li>In the CIP protocol, each atom attached to the chiral center is ranked in order of atomic number (highest = #1, lowest = #4).\u00a0 (We go further down the chain in the event of ties. )<\/li>\n<li>With the #4 substituent in the back: if #1, #2, and #3 trace a clockwise path, the chiral center is assigned <em>(R)<\/em>. If they trace a counterclockwise path the chiral center is <em>(S)<\/em>.<\/li>\n<li>When #4 is in the front or on the side, some useful tips and tricks can be used to avoid having to rotate the whole molecule (<span style=\"color: #993366;\"><em>See also: <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/01\/24\/how-to-draw-enantiomer\/\">How To Draw The Enantiomer of A Chiral Molecule<\/a><\/em><\/span>).<\/li>\n<li>For breaking ties, it&#8217;s useful to keep track of which carbons you&#8217;re working on with the &#8220;dot method&#8221;.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-36020\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2016\/10\/0-summary-how-to-assign-R-S-based-on-CIP-Cahn-Ingold-Prelog-rules.gif\" alt=\"summary-how to assign R S based on CIP Cahn Ingold Prelog rules\" width=\"640\" height=\"703\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Chiral Centers And The Problem Of Naming<\/a><\/li>\n<li><a href=\"#two\">The Cahn-Ingold-Prelog System For Naming Chiral Centers<\/a><\/li>\n<li><a href=\"#three\">Oh No! What Do We Do When #4 Is Not In The Back?<\/a><\/li>\n<li><a href=\"#four\">Assigning R\/S When #4 Is In The Front: A Short Cut<\/a><\/li>\n<li><a href=\"#five\">Assigning R\/S When #4 Is In The Plane Of The Page<\/a><\/li>\n<li><a href=\"#six\">Breaking Ties With The &#8220;Dot Technique&#8221;<\/a><\/li>\n<li><a href=\"#seven\">Conclusion: Assigning R and S With CIP<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quizzes\">Quiz Yourself!<\/a><\/li>\n<li><a href=\"#references\">(Advanced) References and Further Reading<\/a><\/li>\n<\/ol>\n<hr \/>\n<p><strong>This post was co-authored by Matt Pierce of <a href=\"http:\/\/organicchemistrysolutions.com\">Organic Chemistry Solutions<\/a>.\u00a0 Ask Matt about scheduling an online tutoring session <a href=\"https:\/\/masterorganic.wufoo.com\/forms\/q1yg3qx8076h7gx\/\">here<\/a>.<\/strong><\/p>\n<h2><a id=\"one\"><\/a>1. Chiral Centers And The Problem Of Naming<\/h2>\n<p>Previously on MOC we&#8217;ve described <a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/11\/29\/on-cats-part-4-enantiocats\/\"><strong>enantiomers<\/strong><\/a>: molecules that are non-superimposable mirror images of each other. Perhaps the most memorable example is these &#8220;enantiocats&#8221;.<\/p>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14644\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-drawing-of-enantiocats-master-organic-chemistry-graeme-mackay-look-at-the-legs.png\" alt=\"drawing-of-enantiocats-master-organic-chemistry-graeme-mackay-look-at-the-legs\" width=\"490\" height=\"271\" srcset=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-drawing-of-enantiocats-master-organic-chemistry-graeme-mackay-look-at-the-legs.png 511w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-drawing-of-enantiocats-master-organic-chemistry-graeme-mackay-look-at-the-legs-300x166.png 300w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-drawing-of-enantiocats-master-organic-chemistry-graeme-mackay-look-at-the-legs-320x177.png 320w, https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-drawing-of-enantiocats-master-organic-chemistry-graeme-mackay-look-at-the-legs-360x199.png 360w\" sizes=\"(max-width: 490px) 100vw, 490px\" \/><\/p>\n<p>Each of these cats is said to be &#8220;chiral&#8221;: they lack a\u00a0plane of symmetry.<\/p>\n<p>What causes <em>molecules<\/em> to have chirality?<\/p>\n<p>The most common source of chirality is a &#8220;chiral centre&#8221;: typically a\u00a0<strong>tetrahedral<\/strong> carbon attached to four different &#8220;groups&#8221;, or &#8220;substituents&#8221;. \u00a0For each chiral centre there are\u00a0<strong>two<\/strong>\u00a0(and only two!) different ways of arranging the 4 different substituents, which gives rise to two different <strong>configurations.\u00a0<\/strong><span style=\"color: #993366;\"><em>[If you don&#8217;t believe there are only two, see <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/01\/24\/the-single-swap-rule\/\">Single Swap Rule<\/a>].<\/em><\/span><\/p>\n<p>The purpose of this post is to introduce and describe the nomenclature we use to describe these configurations: <strong>the (R)\/(S) notation, or Cahn-Ingold Prelog Rules.<\/strong><\/p>\n<p>Let&#8217;s look at a simple example.<\/p>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14645\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-how-do-we-name-enantiomers-two-molecules-cannot-be-exactly-the-same-since-they-cannot-be-superimposed-stereoisomers-how-do-we-name.gif\" alt=\"how-do-we-name-enantiomers-two-molecules-cannot-be-exactly-the-same-since-they-cannot-be-superimposed-stereoisomers-how-do-we-name\" width=\"641\" height=\"264\" \/><\/p>\n<p>Both of these molecules are 1-bromo-1-chloroethane. But they are <em>not<\/em>\u00a0exactly the same molecule, in the same way that your left shoe is not <em>exactly<\/em> the same as your right. They are non-superimposable mirror images of each other. How do we communicate this difference?<\/p>\n<p>One way would be to describe their physical properties. For example, although these two molecules have the same boiling point, melting point, and share many other physical properties, they rotate plane-polarized light in equal and opposite directions, a property called\u00a0<strong>optical rotation<\/strong> (<em>See <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/02\/07\/optical-rotation-optical-activity-and-specific-rotation\/\">Optical Rotation and Optical Activity<\/a><\/em>) We could use (+)-1-bromo-1-chloroethane to refer to the isomer that rotates polarized light to the right (clockwise, or &#8220;dextrorotatory&#8221;) and use (-)-1-bromo-1-chloroethane to refer to the isomer that rotates polarized light to the left (counterclockwise, or &#8220;levorotatory&#8221;).<\/p>\n<p>However this nomenclature suffers from a serious problem. <strong>There is no simple correlation between the arrangement of substituents around a chiral centre and the direction in which polarized light is rotated<\/strong>. Another solution is needed.<\/p>\n<h2><strong><a id=\"two\"><\/a>2. The Cahn Ingold Prelog (CIP) System For Naming Chiral Centers<\/strong><\/h2>\n<p>A solution to this quandary was proposed by Robert Cahn, Chris Ingold, and Vladimir Prelog in 1966. The resulting &#8220;CIP&#8221; protocol works as follows:<\/p>\n<ol>\n<li>Prioritize the four groups around a chiral center <strong>according to atomic number<\/strong>. The highest atomic number is assigned priority #1, and the lowest atomic number is assigned priority #4.<\/li>\n<li>Orient the chiral centre such that\u00a0the #4 priority substituent is pointing<strong> away<\/strong> from the viewer. For our purposes, it&#8217;s enough for it merely to be attached to a &#8220;dashed&#8221; bond.<\/li>\n<li>Trace the path of priorities #1, #2 and #3. (For this part you ignore #4).\n<ol>\n<li>If the path traced from 1-2-3 \u00a0 is<strong> clockwise<\/strong>, the chiral center is assigned (<em>R<\/em>) (from Latin,\u00a0<em>rectus<\/em>)<\/li>\n<li>If the path traced is<strong> counter clockwise<\/strong>, the chiral center is assigned (<em>S<\/em>) (from the Latin\u00a0<em>sinister)<\/em><\/li>\n<li>Now we have a better way to describe molecules [A] and [B] shown above. Molecule [A] is named (<em>R<\/em>)-1-bromo-1-chloroethane, and molecule [B] is named (<em>S<\/em>)-1-bromo-1-chloroethane:<\/li>\n<\/ol>\n<\/li>\n<\/ol>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14646\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-apply-cahn-ingold-prelog-cip-rules-to-determine-r-s-on-a-chiral-center-how-to-do-it.gif\" alt=\"apply-cahn-ingold-prelog-cip-rules-to-determine-r-s-on-a-chiral-center-how-to-do-it\" width=\"640\" height=\"569\" \/><\/p>\n<p>We should reiterate that<strong> the designations (R) and (S) bear\u00a0no relationship to whether a molecule rotates plane-polarized light clockwise (+) or counterclockwise (-).<\/strong> For example the most common naturally occurring configuration of the amino acid <a href=\"https:\/\/en.wikipedia.org\/wiki\/Alanine\"><strong>alanine<\/strong><\/a> is (S), but its optical rotation (in aqueous acid solution) is (+).<\/p>\n<h2><a id=\"three\"><\/a>3. What About When #4 Is Not In The Back?<\/h2>\n<p>That seems simple enough! &#8220;Is that it?&#8221;, you might ask.<\/p>\n<p>Uh, no.\u00a0As it happens, there&#8217;s a few bumps in the road toward determining (R)\/(S) once we get beyond the simple example above.<\/p>\n<p>These &#8220;trickier cases&#8221; fall into three main categories.<\/p>\n<ol>\n<li><strong>What if the #4 substituent is not helpfully pointing away from the viewer<\/strong>, as it was in our example above?\u00a0What if it&#8217;s in the &#8220;front&#8221; (i.e. attached to a &#8220;wedged&#8221; bond) or, heaven forbid, in the plane of the page?<\/li>\n<li><strong>Assigning priorities in complex situations<\/strong>. What do we do in situations where a chiral centre has two or more identical atoms attached? In other words,<strong> how do we break ties?\u00a0<\/strong><\/li>\n<li>What do we do if the molecule is <strong>drawn a peculiar way<\/strong>, such as in\u00a0<strong>Fischer or Newman projections<\/strong>?<\/li>\n<\/ol>\n<p><span style=\"color: #993366;\"><em>We&#8217;re not going to be able to fully address all of these issues in this post. But we can certainly deal with #1 and make some headway with #2. For #3, see <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2019\/05\/21\/how-to-determine-r-and-s-configurations-on-a-fischer-projection\/\">How To Determine R\/S On A Fischer Projection<\/a> and <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2017\/02\/01\/assigning-rs-to-newman-projections-and-converting-newman-to-line-diagrams\/\">How to Determine R\/S on a Newman Projection<\/a><\/em><\/span><\/p>\n<h2><strong><a id=\"four\"><\/a>4. Determining R\/S When The #4 Substituent Is In Front (i.e. on a &#8220;Wedge&#8221;): A Short Cut<\/strong><\/h2>\n<p>Let&#8217;s\u00a0first consider the molecule below. The name of this molecule is (<em>R<\/em>)-1-fluoroethanol. It is listed below with priorities assigned based on atomic number. In this case F&gt;O&gt;C&gt;H. So F is #1 and H is #4. The tricky part here is that the #4 priority is pointing <strong>out<\/strong> of the page (on a &#8220;wedge&#8221;).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14647\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-how-do-we-determine-r-and-s-when-group-4-is-in-the-front-on-a-wedge.gif\" alt=\"how-do-we-determine-r-and-s-when-group-4-is-in-the-front-on-a-wedge\" width=\"640\" height=\"149\" \/><\/p>\n<p>How do we determine (R)\/(S) in this case? \u00a0There are two ways to do it.<\/p>\n<p>Many instructors\u00a0will tell you to \u201csimply\u201d rotate the molecule in your head so that the #4 priority is on a dash. Then you can assign <em>R <\/em>or <em>S <\/em>in the traditional way. This &#8220;simple&#8221; advice is not always an easy task for beginners.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14648\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-determining-r-and-s-when-number-4-group-is-on-a-wedge-flip-entire-molecule-180-but-you-dont-need-to-do-that.gif\" alt=\"etermining-r-and-s-when-number-4-group-is-on-a-wedge-flip-entire-molecule-180-but-you-dont-need-to-do-that\" width=\"641\" height=\"301\" \/><\/p>\n<p>Thankfully, it\u00a0is technically unnecessary to perform such a mental rotation.<\/p>\n<p>Here&#8217;s \u00a0a way around this. When the #4 priority is on a wedge you can just <strong>reverse the rules.<\/strong> So now we have two sets of rules:<\/p>\n<p>If the #4 priority is on a <strong>dash<\/strong>:<\/p>\n<ul>\n<li>Clockwise = <em>R<\/em><\/li>\n<li>Counterclockwise = <em>S<\/em><\/li>\n<\/ul>\n<p>If the #4 priority is on a <strong>wedge<\/strong>, reverse the typical rules:<\/p>\n<ul>\n<li>Clockwise = <em>S<\/em><\/li>\n<li>Counterclockwise = <em>R<\/em><\/li>\n<\/ul>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14649\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-determining-r-s-when-number-4-is-on-a-wedge-apply-opposite-rule-just-determine-r-s-as-usual-but-flip-the-result-you-get-opposite-rules.gif\" alt=\"determining-r-s-when-number-4-is-on-a-wedge-apply-opposite-rule-just-determine-r-s-as-usual-but-flip-the-result-you-get-opposite-rules\" width=\"626\" height=\"260\" \/><\/p>\n<p><em>R<\/em> and <em>S<\/em> can easily be assigned to either picture of the molecule. I still encourage you to use a model kit and learn how to do so, however. Organic chemistry is much easier to understand, and much more beautiful, if you can master how to visualize a tetrahedral carbon atom.<\/p>\n<p><span style=\"color: #993366;\"><em>See also, <span style=\"color: #993366;\"><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><\/span><\/p>\n<h2><a id=\"five\"><\/a>5. Determining R\/S When The #4 Group Is In The Plane Of The Page?<\/h2>\n<p>What if the #4 priority is in the plane of the paper, for example on a line? In this case it\u2019s impossible to assign <em>R <\/em>and S in the traditional way. You&#8217;d have a 50:50 shot of getting it correct: not good odds. Again, if you can redraw the molecule in your head, then it\u2019s better to just do that. If you can\u2019t do this reliably then you need to learn the \u201csingle swap\u201d concept.<\/p>\n<p>Here&#8217;s how it works.\u00a0<strong>Swapping any two groups\u00a0on a chiral\u00a0centre will flip the configuration of the chiral\u00a0centre\u00a0from R to S (and vice versa). [<a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/01\/24\/how-to-draw-enantiomer\/\">We previously talked about the &#8220;single swap rule&#8221; here<\/a>]<\/strong><\/p>\n<p>Knowing this, we can do a nifty trick.<\/p>\n<ol>\n<li>Take the #4 substituent (in the plane of the page) and\u00a0<strong>swap<\/strong> it with the substituent\u00a0in the back <span style=\"color: #993366;\"><em>[If the configuration is R, this will switch it to S. If the configuration is S, this will flip it to R. We&#8217;ll need to account for this in step #3].<\/em><\/span><\/li>\n<li>Redraw the chiral centre, and determine R\/S on the new chiral centre which now has group #4 in the back.<\/li>\n<li>\u00a0Whatever result you got,\u00a0<strong>flip<\/strong> it to its opposite to account for the fact that you did a single swap in step #1.<\/li>\n<\/ol>\n<p>Here&#8217;s an example. Note that here\u00a0\u00a0I first switched #4 and #3, but the main point is to switch two groups so that #4 is out of the plane of the paper.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14650\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-how-to-determine-r-s-when-group-number-4-is-in-plane-of-page-swap-group-in-plane-with-group-in-back-determine-r-s-and-then-flip-result.gif\" alt=\"how-to-determine-r-s-when-group-number-4-is-in-plane-of-page-swap-group-in-plane-with-group-in-back-determine-r-s-and-then-flip-result\" width=\"640\" height=\"688\" \/><\/p>\n<p>This method always works, assuming you&#8217;ve determined the four priorities accurately. (It also works for cases when #4 is on a wedge).<\/p>\n<p>However, sometimes we&#8217;re not in the position of dealing with 4 different atoms attached to a chiral carbon. For instance, it&#8217;s possible to\u00a0have chiral carbons which are attached to 4\u00a0<em>carbons<\/em>. So how do we break the ties in these cases?<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14651\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/8-not-every-chiral-center-is-attached-to-four-different-atoms-how-do-we-break-ties-in-these-situations.gif\" alt=\"not-every-chiral-center-is-attached-to-four-different-atoms-how-do-we-break-ties-in-these-situations\" width=\"640\" height=\"245\" \/><\/p>\n<h2><a id=\"six\"><\/a>6. Determining CIP Priorities: Breaking &#8220;Ties&#8221; With The &#8220;Dot Technique&#8221;<\/h2>\n<p>The quick answer is to use the &#8220;dot technique&#8221;. Here&#8217;s how it works. Let&#8217;s do it for 4-ethyl-4-methyloctane, above.<\/p>\n<ol>\n<li>Go outward from the chiral centre to each of the surrounding 4 atoms and\u00a0assign priorities (based on atomic number) to each of these atoms. [Sometimes it&#8217;s helpful to draw\u00a0<em>dots<\/em> on each of these atoms.]<\/li>\n<\/ol>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14652\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/9-determine-c-i-p-priorities-breaking-ties-with-the-dot-technique-evaluate-4-atoms-directly-attached-to-chiral-center-for-priority.gif\" alt=\"determine-c-i-p-priorities-breaking-ties-with-the-dot-technique-evaluate-4-atoms-directly-attached-to-chiral-center-for-priority\" width=\"641\" height=\"158\" \/><a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2016\/10\/7a-e1476913944955.png\"><br \/>\n<\/a>2. If there is a tie, list the atoms attached to each of those dotted atoms in decreasing order of atomic number.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14653\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/10-to-break-ties-list-all-3-atoms-attached-to-dotted-atoms-in-decreasing-order-of-atomic-number-method-of-dots.gif\" alt=\"to-break-ties-list-all-3-atoms-attached-to-dotted-atoms-in-decreasing-order-of-atomic-number-method-of-dots\" width=\"641\" height=\"189\" \/><\/p>\n<p>3. Compare each list, atom by atom. In our example, since C&gt;H, (C,H,H) takes priority over (H,H,H) so the CH<sub>3<\/sub> group is assigned priority #4.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14654\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/11-step-3-breaking-ties-cip-rank-lists-according-to-priority-of-substituents-list-3-groups.gif\" alt=\"step-3-breaking-ties-cip-rank-lists-according-to-priority-of-substituents-list-3-groups\" width=\"640\" height=\"183\" \/><\/p>\n<p>4. If there is still a tie, move the dots to the highest ranking atom in the list (i.e. the atom with highest atomic number). <strong>The dots are helpful because they help you to keep track of where you are, which can be important in complex examples.<\/strong><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14655\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/12-step-4-in-determinine-cip-when-there-are-ties-method-of-dots-move-dots-and-repeat.gif\" alt=\"step-4-in-determinine-cip-when-there-are-ties-method-of-dots-move-dots-and-repeat.\" width=\"640\" height=\"167\" \/><\/p>\n<p>5. In this case, we keep moving along the chain. By the way, if you ever reach the end of the chain without determining a difference, that means that the groups are identical and it isn&#8217;t a chiral centre after all.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14656\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/13-method-of-dots-breaking-ties-determining-r-s-cip-rules-move-dots-assign-priorities.gif\" alt=\"method-of-dots-breaking-ties-determining-r-s-cip-rules-move-dots-assign-priorities\" width=\"639\" height=\"226\" \/><\/p>\n<p>6. By this point we have enough information to assign (R)\/(S). Since priority #4 is in the front, we can also break out our &#8220;opposite rule&#8221; for good measure:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14657\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/14-step-6-in-breaking-ties-cip-rules-r-s-assign-r-s-use-opposite-rules-if-necessary.gif\" alt=\"step-6-in-breaking-ties-cip-rules-r-s-assign-r-s-use-opposite-rules-if-necessary\" width=\"640\" height=\"235\" \/><\/p>\n<h2><a id=\"seven\"><\/a>7. Conclusion: The Cahn-Ingold-Prelog Rules For Assigning R and S Configurations<\/h2>\n<p>In the next post we&#8217;ll go into some trickier examples with determining R\/S, including how to deal with double bonds, rings, and isotopes. In a future post, we&#8217;ll get into determining R\/S in the Fischer and Newman projections.<\/p>\n<p><strong>Thanks to Matt Pierce for making major contributions to this article.\u00a0\u00a0<\/strong><\/p>\n<p><strong>Ask Matt about scheduling an online tutoring session\u00a0<a href=\"https:\/\/masterorganic.wufoo.com\/forms\/q1yg3qx8076h7gx\/\">here<\/a>.<\/strong><\/p>\n<hr \/>\n<h2><a id=\"notes\"><\/a>Notes<\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/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\/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\/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\/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\/2010\/11\/29\/on-cats-part-4-enantiocats\/\" class=\"\"><span>On Cats, Part 4: Enantiocats<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/12\/15\/on-cats-part-6-stereocenters\/\" class=\"\"><span>On Cats, Part 6: Stereocenters<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/organic-chemistry-practice-problems\/stereochemistry-practice-problems-and-quizzes\/\" class=\"\"><span>Stereochemistry Practice Problems and Quizzes (MOC Membership)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2023\/11\/06\/bond-rotation-how-to-draw\/\" class=\"\"><span>How To Draw A Bond Rotation<\/span><\/a><\/li><\/ul><\/div>\n<hr \/>\n<h2><a id=\"quizzes\"><\/a>Quiz Yourself!<\/h2>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0802-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. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0803-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. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0807-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. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0814-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. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0810-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. <br \/>\n<\/p>\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0812-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><a id=\"references\"><\/a>(Advanced) References and Further Reading<\/h2>\n<ol>\n<li><strong>Specification of Molecular Chirality<br \/>\n<\/strong>R. S. Cahn, Sir Christopher Ingold, V. Prelog<strong><br \/>\n<\/strong><em>Angew. Chem. Int. Ed.<\/em><strong> 1966, <\/strong><em>5<\/em> (4), 385-415<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.196603851\">10.1002\/anie.196603851<\/a><br \/>\nThis is not the first paper on the topic by the authors (see Refs. 4 and 5), but it is a major publication and an attempt to consolidate all the information on chirality in a single place. This paper discusses the various types of chirality possible in chemistry (not just at tetrahedral carbons!) and how to assign chirality unambiguously.<\/li>\n<li><strong>Basic Principles of the CIP\u2010System and Proposals for a Revision<br \/>\n<\/strong> Dr. Vladlmir Prelog and Prof. Dr. G\u00fcnter Helmchen<strong><br \/>\n<\/strong><em>Angew. Chem. Int. Ed.<\/em><strong> 1982<\/strong>, 21 (8), 567-583<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.198205671\">10.1002\/anie.198205671<\/a><br \/>\nAn update to Ref. #1, which addresses a lot of edge cases that may come up in complex stereochemical assignments.<\/li>\n<li><strong>CHIRALITY IN CHEMISTRY<br \/>\n<\/strong>Vladimir Prelog<strong><br \/>\n<\/strong><a href=\"https:\/\/www.nobelprize.org\/prizes\/chemistry\/1975\/prelog\/lecture\/\">Nobel Lecture, 1975<\/a><br \/>\nPrelog\u2019s Nobel Lecture. Nobel Lectures are fascinating to read as they give insight into the life of scientists and the path to discovery, which is rarely linear.<\/li>\n<li><strong>&#8220;Absolutely&#8221; simple stereochemistry<\/strong><br \/>\nPhilip S. Beauchamp<br \/>\n<em>Journal of Chemical Education<\/em> <strong>1984,<\/strong> <em>61<\/em> (8), 666<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ed061p666\">10.1021\/ed061p666<\/a><br \/>\nThis paper describes a simple method for determining stereochemistry of tetrahedral carbons using the hands, suitable for undergraduate students of organic chemistry.<\/li>\n<li><strong>A simple hand method for Cahn-Ingold-Prelog assignment of R and S configuration to chiral carbons<br \/>\n<\/strong>Martin P. Aalund and James A. Pincock<br \/>\n<em>Journal of Chemical Education<\/em> <strong>1986,<\/strong> <em>63<\/em> (7), 600<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ed063p600\">10.1021\/ed063p600<\/a><br \/>\nA follow-up to the previous paper (Ref #4), but sadly it is incomplete!<\/li>\n<li><strong>A Web-Based Stereochemistry Tool to Improve Students\u2019 Ability to Draw Newman Projections and Chair Conformations and Assign R\/S Labels<\/strong><br \/>\nNimesh Mistry, Ravi Singh, and Jamie Ridley<br \/>\n<em>Journal of Chemical Education<\/em> <strong>2020,<\/strong> <em>97<\/em> (4), 1157-1161<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/acs.jchemed.9b00688\">10.1021\/acs.jchemed.9b00688<\/a><br \/>\nThis paper discusses a web-based tool that helps students with visualization of chiral compounds and assignment of stereochemistry as per the Cahn-Ingold-Prelog (CIL) rules. See ref. 34 in the paper for the link.<\/li>\n<\/ol>\n<p>&#8216;,&#8217;Introduction to Assigning (R) and (S): The Cahn-Ingold-Prelog Rules<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Assigning\u00a0R and\u00a0S Configurations With the Cahn-Ingold-Prelog (CIP) Rules Enantiomers are stereoisomers that are non-superimposable mirror images of each other (by the way, molecules that are <\/p>\n","protected":false},"author":1,"featured_media":36020,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1413],"tags":[879,1133,1131,1134,1132],"post_folder":[],"class_list":["post-10198","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-stereochemistry-chirality","tag-cahn-ingold-prelog","tag-chiral-centers","tag-r-and-s","tag-single-swap-rule","tag-stereochemistry-enantiomers"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Introduction to Assigning (R) and (S): The Cahn-Ingold-Prelog Rules<\/title>\n<meta name=\"description\" content=\"Assigning R and S with the Cahn-Ingold-Prelog rules. 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