{"id":10487,"date":"2017-02-24T18:02:01","date_gmt":"2017-02-25T00:02:01","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=10487"},"modified":"2026-05-06T19:36:56","modified_gmt":"2026-05-07T00:36:56","slug":"optical-purity-and-enantiomeric-excess","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/","title":{"rendered":"Optical Purity and Enantiomeric Excess"},"content":{"rendered":"<p><strong>All About Optical Purity and Enantiomeric Excess<\/strong><\/p>\n<p>What is a racemic mixture? What is &#8220;optically active&#8221;, &#8220;optically inactive&#8221;, and &#8220;optically pure&#8221;. What do the terms, &#8220;<em>l&#8221;\u00a0<\/em>and &#8220;<em>d<\/em>&#8221; mean? What is the formula for optical purity? What is the difference between optical purity and enantiomeric excess? [OK, that one&#8217;s quick: they&#8217;re the same thing].<\/p>\n<p>In this post we answer all these burning questions, and do some worked examples of optical purity and enantiomeric excess besides.<\/p>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-37392\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2017\/02\/0-summary-of-optical-rotation-enantiomeric-excess-optical-purity.gif\" alt=\"summary of optical rotation enantiomeric excess optical purity\" width=\"640\" height=\"547\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Louis Pasteur and The Discovery Of &#8220;Enantiomers&#8221;<\/a><\/li>\n<li><a href=\"#two\">A Racemic Mixture Is An Equal Mixture Of Two Enantiomers And Has A Specific Rotation of 0\u00b0 (Optically Inactive)<\/a><\/li>\n<li><a href=\"#three\">An &#8220;Optically Pure&#8221; Solution Contains Only One Enantiomer<\/a><\/li>\n<li><a href=\"#four\">The Terms &#8220;<em>l-<\/em>&#8221; And &#8220;<em>d-<\/em>&#8221; Refer To The &#8220;Levorotatory (\u2013)&#8221; And &#8220;Dextrorotatory (+)&#8221; Forms Of Each Enantiomer<\/a><\/li>\n<li><a href=\"#five\">The Formula For Optical Purity<\/a><\/li>\n<li><a href=\"#six\">Using &#8220;Optical Purity&#8221; To Determinine The Molar Composition Of A Mixture<\/a><\/li>\n<li><a href=\"#seven\">Optical Purity = Enantiomeric Excess<\/a><\/li>\n<li><a href=\"#eight\">Another Practice Problem For Enantiomeric Excess<\/a><\/li>\n<li><a href=\"#nine\">An Optical Purity Practice Problem<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quizzes\">Quiz Yourself!<\/a><\/li>\n<\/ol>\n<hr \/>\n<p><strong>This post was co-authored with Matt Pierce of\u00a0<a href=\"http:\/\/organicchemistrysolutions.com\">Organic Chemistry Solutions<\/a>.\u00a0 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=\"one\"><\/a>1. Louis Pasteur And The Discovery Of\u00a0 &#8220;Enantiomers&#8221;<\/h2>\n<p>In our last post on optical rotation (<em><span style=\"color: #993366;\">See post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/02\/07\/optical-rotation-optical-activity-and-specific-rotation\/\">Optical Rotation, Optical Activity, and Specific Rotation<\/a><\/span>)<\/em>\u00a0we saw that when Louis Pasteur crystallized a salt of a compound then known as &#8220;racemic acid&#8221; he discovered that it formed two different types of crystals.<\/p>\n<p>When redissolved in water, one set of crystals rotated plane-polarized light clockwise (dextrorotatory, &#8220;to the right&#8221;).<\/p>\n<p>The other set of crystals rotated plane-polarized light <strong>to exactly the same extent<\/strong>, but\u00a0counterclockwise (levorotatory, &#8220;to the left&#8221;).<\/p>\n<p>This was surprising for two reasons.<\/p>\n<ul>\n<li>First, racemic acid was thought at the time to be a single compound. It turned out to be a 50:50 mixture of <em>two<\/em> compounds!<\/li>\n<li>Second, racemic acid did not rotate plane-polarized light: in other words, it was <strong>optically inactive<\/strong>.\u00a0However, each of the two components were themselves\u00a0<strong>optically active<\/strong>: they rotated plane polarized light to equal and opposite extents.<\/li>\n<\/ul>\n<p>This immediately explained why racemic acid is optically inactive: just like two equal and opposite vectors cancel to give zero, the equal and opposite rotations due to each component cancel each other out.<\/p>\n<p>Pasteur also noticed that the crystal forms were mirror images of each other. Then, in a leap of insight made without knowing the precise structure of the molecule, he then proposed that the <em>molecules themselves<\/em> were mirror images of each other. \u00a0[<a href=\"#noteone\">Note 1<\/a>]<\/p>\n<p>We now know this to be true. We call two molecules that are non-superimposable mirror images of each other, &#8220;enantiomers&#8221;.<\/p>\n<p><span style=\"color: #993366;\"><em>(Molecules that are superimposable mirror images, we just call, &#8220;the same molecule&#8221;. In chemistry, &#8220;\u2200&#8221; is just &#8220;A&#8221; that&#8217;s been rotated)<\/em><\/span><\/p>\n<h2><a id=\"two\"><\/a>2. A Racemic Mixture Is An Equal Mixture Of Two Enantiomers And Has A Specific Rotation of 0\u00b0 (Optically Inactive)<\/h2>\n<p>The two components of &#8220;racemic acid&#8221; are (2S,3S)-tartaric acid, which is levorotatory, or (\u2013); and (<em>2R, 3R<\/em>) tartaric acid, which is dextrotoratory, or (+). They are <strong>enantiomers<\/strong> of each other: stereoisomers which are non-superimposable mirror images.<\/p>\n<p>We now use the term &#8220;racemic mixture&#8221; to refer to a 50:50 mixture of two enantiomers.\u00a0(&#8220;Racemic&#8221; comes from the Latin <em>racemus<\/em>, or &#8220;a bunch of grapes&#8221;, a nod to the\u00a0fact that\u00a0tartaric acid crystals are also known as &#8220;wine diamonds&#8221;)<\/p>\n<p>So Pasteur&#8217;s achievement was the first\u00a0<strong>resolution<\/strong> of a racemic mixture.<\/p>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14757\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-pasteur-achievement-in-1848-resolution-of-racemic-acid-into-two-enantiomers-of-tartaric-acid.gif\" alt=\"pasteur-achievement-in-1848-resolution-of-racemic-acid-into-two-enantiomers-of-tartaric-acid\" width=\"625\" height=\"687\" \/><\/p>\n<h2><a id=\"three\"><\/a>3. An &#8220;Optically Pure&#8221; Solution Contains Only One Enantiomer<\/h2>\n<p>As we said, the two enantiomers of tartaric acid rotate plane-polarized light to equal and opposite extents. In the last post we introduced a more precise\u00a0way of saying this, in that the two enantiomers of tartaric acid have equal and opposite\u00a0<strong>specific rotations.\u00a0<\/strong><\/p>\n<p><img decoding=\"async\" class=\"aligncenter wp-image-14758\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-pure-crystals-of-tartaric-acid-opposite-enantiomers-opposite-specific-rotations.gif\" alt=\"pure-crystals-of-tartaric-acid-opposite-enantiomers-opposite-specific-rotations\" width=\"640\" height=\"362\" \/><\/p>\n<p>These &#8220;specific rotations&#8221; have to be measured experimentally: there&#8217;s no simple correlation between the configuration of a chiral centre (<em>R<\/em> or <em>S<\/em>) and the optical rotation.<\/p>\n<p>This term &#8220;specific rotation&#8221; means that for the given concentration, temperature, wavelength, and solvent<\/p>\n<ul>\n<li>An &#8220;optically pure&#8221; (or &#8220;enantiomerically pure&#8221;) solution of 100% (<em>S,S<\/em>) tartaric acid and 0% (<em>R,R<\/em>) tartaric acid will have an optical rotation of \u201312\u00b0.<\/li>\n<li>An &#8220;optically pure&#8221; solution of 100% (<em>R,R<\/em>) tartaric acid and 0% (<em>S,S<\/em>) tartaric acid will have an optical rotation of +12\u00b0 .<\/li>\n<\/ul>\n<p>We&#8217;ve also seen that a &#8220;racemic mixture&#8221; of 50% (<em>S,S<\/em>) tartaric acid and 50% (<em>R,R<\/em>) tartaric acid will have an optical rotation of 0\u00b0.<\/p>\n<h2><a id=\"four\"><\/a>4. The Terms &#8220;<em>l-<\/em>&#8221; And &#8220;<em>d-<\/em>&#8221; Refer To The &#8220;Levorotatory (\u2013)&#8221; And &#8220;Dextrorotatory (+)&#8221; Forms Of Each Enantiomer<\/h2>\n<p>If we call the &#8220;levorotatory&#8221; (\u2013) form of tartaric acid \u00a0&#8220;<em>l-<\/em>&#8221; \u00a0and the &#8220;dextrorotatory&#8221; (+) form of tartaric acid &#8220;<em>d-<\/em>&#8220;, then we can make the following three points on a graph.<span style=\"color: #993366;\">\u00a0<em>[note: in the real world, this graph is not always so linear, but it will do for our purposes]<\/em><\/span><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14759\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-optical-rotation-versus-molar-composition-tartaric-acid-optically-inactive-for-50-50.gif\" alt=\"optical-rotation-versus-molar-composition-tartaric-acid-optically-inactive-for-50-50\" width=\"725\" height=\"478\" \/><\/p>\n<p>100% optically pure\u00a0<em>l<\/em>-tartaric acid has a specific rotation of \u201312\u00b0, which gradually rises\u00a0to 0\u00b0 as the proportion of the\u00a0<em>d<\/em> enantiomer is raised to 50%. As the the molar composition of the\u00a0<em>d<\/em> form increases, so does the optical rotation, going up to +12\u00b0 again for the optically pure\u00a0<em>d<\/em>-enantiomer.<\/p>\n<h2><strong><a id=\"five\"><\/a>5. The Formula For Optical Purity<\/strong><\/h2>\n<p>This suggests an idea. Let&#8217;s say you had a\u00a0<strong>non-racemic<\/strong> but\u00a0<strong>optically impure<\/strong> mixture of\u00a0<em>l<\/em> and\u00a0<em>d<\/em> enantiomers, a situation that arises quite frequently in modern organic chemistry [<a href=\"#notetwo\">Note 2<\/a>].<\/p>\n<p>By measuring the optical rotation of the mixture for a compound whose specific rotation is known, \u00a0you can figure out its <strong>optical purity<\/strong> and could work backwards to determine the ratio of enantiomers. [<a href=\"#notethree\">Note 3<\/a>]<\/p>\n<p>For example, let&#8217;s say you had a mixture of enantiomers of tartaric acid that has an observed rotation of +6\u00b0 .<\/p>\n<p>We can define the\u00a0<strong>optical purity\u00a0<\/strong>as the <strong>observed rotation<\/strong> of a mixture divided by the <strong>specific rotation<\/strong> of the pure enantiomer (obtained under identical conditions).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14760\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-optical-purity-equals-observed-rotation-of-mixture-divided-by-specific-rotation-of-pure-enantiomer.gif\" alt=\"optical-purity-equals-observed-rotation-of-mixture-divided-by-specific-rotation-of-pure-enantiomer\" width=\"639\" height=\"85\" \/><\/p>\n<p>For our solution of tartaric acid with an observed rotation of +6\u00b0, our optical purity would be 50%<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14761\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-optical-purity-of-tartaric-acid-with-observed-rotation-of-6-would-be-50-per-cent.gif\" alt=\"optical-purity-of-tartaric-acid-with-observed-rotation-of-6-would-be-50-per-cent\" width=\"641\" height=\"75\" \/><\/p>\n<h2><a id=\"six\"><\/a>6. Going From &#8220;Optical Purity&#8221; To Determining The Molar Composition Of The Mixture<\/h2>\n<p>Now comes the part which\u00a0sometimes\u00a0trips people up.\u00a0<em>What&#8217;s the molar composition of the mixture?<\/em><\/p>\n<p>Your first answer might be 50:50. \u00a050%\u00a0<em>d-<\/em> and 50%\u00a0<em>l- .\u00a0<\/em><\/p>\n<p>But when you think about it, that can&#8217;t be right: a 50-50 mixture would be <strong>racemic<\/strong>, which would have no optical rotation at all!<\/p>\n<p>An &#8220;optical purity&#8221; of 50% actually means that the\u00a0<strong>major\u00a0<\/strong><strong>enantiomer <\/strong>(<em>d- <\/em>in this case, since the solution is dextrorotatory)\u00a0is present in <strong>50% excess over the minor enantiomer.\u00a0<\/strong>(<em>l-)<\/em><\/p>\n<p>The molar composition of the\u00a0<em>l-\u00a0<\/em> and\u00a0<em>d-<\/em> forms must add up to\u00a0100%:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14762\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-molar-composition-of-l-and-d-forms-must-add-to-100-per-cent.gif\" alt=\"molar-composition-of-l-and-d-forms-must-add-to-100-per-cent\" width=\"643\" height=\"84\" \/><\/p>\n<p>So using some basic algebra, we can use these two equations to calculate the ratio of enantiomers.<\/p>\n<p>For instance, in equation #2, \u00a0we can isolate the % of\u00a0<em>d-<\/em> as being (50% + %\u00a0<em>l-<\/em> ). We can then plug that value into equation #1 and we obtain the value for\u00a0<em>% l-\u00a0<\/em> as 25%. The value for\u00a0<em>% d-<\/em> must then be 75%.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14763\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-calculation-of-relative-amounds-of-l-and-d-for-optical-purity.gif\" alt=\"calculation-of-relative-amounds-of-l-and-d-for-optical-purity\" width=\"640\" height=\"219\" \/><\/p>\n<p>So,\u00a0far from\u00a0being 50-50, \u00a0a mixture with 50% optical purity is actually a <strong>75% : 25%<\/strong> mixture of enantiomers.<\/p>\n<p>One way of looking at a 50% value for &#8220;optical purity&#8221; is that it&#8217;s 50% the dominant enantiomer, and 50% a racemic mixture.<\/p>\n<h2><strong><a id=\"seven\"><\/a>7. Optical Purity = Enantiomeric Excess<\/strong><\/h2>\n<p>If you do the math in the above example, \u00a0you&#8217;ll note that the percentage of the\u00a0<em>d<\/em>&#8211; enantiomer (75%) exceeds the percentage of the\u00a0<em>l-\u00a0<\/em>enantiomer (25%) by 50%. This also happens to be the value we calculated for optical purity.<\/p>\n<p>Thus, the optical purity is thus equal to the percentage\u00a0<strong>excess of the major enantiomer over the minor enantiomer.\u00a0<\/strong><\/p>\n<p>This term, the &#8220;enantiomeric excess&#8221;, or &#8220;e.e.&#8221; for short, \u00a0is equivalent to the optical purity and is actually used far more often for expressing the enantiomeric purity of a mixture.<\/p>\n<p>So an &#8220;optically pure&#8221; solution containing 100% of the\u00a0<em>d<\/em> &#8211; enantiomer and 0% of the\u00a0<em>l-\u00a0<\/em>enantiomer would have an enantiomeric excess of:<\/p>\n<p>100% \u2013 0% = 100%<\/p>\n<p>The same would be true for an optically pure solution of the\u00a0<em>l-\u00a0<\/em>enantiomer: 100% e.e.<\/p>\n<p>A racemic mixture, as we saw, has an optical purity of 0%. And so, too, \u00a0the enantiomeric excess is also 0%.<\/p>\n<p>50%<em>d<\/em> \u00a0\u2013 50%\u00a0<em>l\u00a0<\/em>= 0%<\/p>\n<h2><strong><a id=\"eight\"><\/a>8. Another Practice Problem For Enantiomeric Excess<\/strong><\/h2>\n<p>Let&#8217;s do another problem!<\/p>\n<blockquote><p>A sample of 2-bromobutane has an enantiomeric excess (e.e.) of 75% favouring the\u00a0<em>d<\/em>&#8211; enantiomer. What is the percentage of each enantiomer?<\/p><\/blockquote>\n<p>First, identify the relevant equations:<\/p>\n<p>e.e. = %<em>d<\/em> \u2013\u00a0<em>%l\u00a0<\/em> = 75%<\/p>\n<p><em>%<\/em><em>d-<\/em> + %<em>l- \u00a0= 100%<\/em><\/p>\n<p>Next, solve one equation for either variable so you can plug that into the other equation. In this case we arbitrarily solve for the % of the\u00a0<em>d<\/em>&#8211; enantiomer using the second equation.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14764\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/8-percentage-of-d-plus-l-gives-enantiomeric-excess.gif\" alt=\"percentage-of-d-plus-l-gives-enantiomeric-excess\" width=\"640\" height=\"105\" \/><\/p>\n<p>Now, plug in what we found to the first equation, solving in this case for the percent of the\u00a0<em>d-<\/em> enantiomer.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14765\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/9-solve-for-percentage-of-l-enantiomer.gif\" alt=\"solve-for-percentage-of-l-enantiomer\" width=\"641\" height=\"99\" \/><\/p>\n<p>Then, solve for %<em>d<\/em> with our knowledge that the total equals 100%.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14766\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/10-mixture-with-75-per-cent-e-e-is-87-5-major-and-12-5-minor.gif\" alt=\"mixture-with-75-per-cent-e-e-is-87-5-major-and-12-5-minor\" width=\"636\" height=\"79\" \/><\/p>\n<p>The previous two steps contain the answer, but we can also double check by plugging these numbers into the equation for e.e. \u00a0<a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2017\/02\/7-equations-1.png\"><br \/>\n<\/a> <img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14767\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/11-enantiomeric-excess.gif\" alt=\"enantiomeric-excess\" width=\"644\" height=\"78\" \/><\/p>\n<p>So a mixture with 75% ee is actually composed of 87.5% of the major enantiomer, and 12.5% of the minor enantiomer.<\/p>\n<p>As we said above, another way of looking at it is that it&#8217;s 75% composed of the major enantiomer, and 25% of a racemic mixture.<\/p>\n<h2><strong><a id=\"nine\"><\/a>9. An Optical Purity Practice Problem<\/strong><\/h2>\n<p>Let&#8217;s do a slightly different problem, this time using optical purity.<\/p>\n<blockquote><p>A mixture contains 3g of (+)-2-bromobutane and 2g of (\u2013)-2-bromobutane. What is the rotation of the mixture, given that (+)-2-bromobutane has a specific rotation of +23.1\u00b0.<\/p><\/blockquote>\n<p>First, let&#8217;s calculate enantiomeric excess\/optical purity as a decimal number. Note that the units here (grams) will cancel.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14768\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/12-calculation-of-optical-purity-example-grams-bromobutane.gif\" alt=\"calculation-of-optical-purity-example-grams-bromobutane\" width=\"641\" height=\"223\" \/><\/p>\n<p>Now, we&#8217;ll solve for the rotation of the mixture using the equation for optical purity. Again, we&#8217;ll use the decimal form, which is 0.2 , for optical purity (or enantiomeric excess).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-14769\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/13-optical-purity-is-the-same-as-enantiomeric-excess.gif\" alt=\"optical-purity-is-the-same-as-enantiomeric-excess\" width=\"725\" height=\"230\" \/><\/p>\n<p>This gives us a rotation of 4.62\u00b0 for the mixture.<\/p>\n<p>That&#8217;s it! By the way, this is about as intense as math will ever get in introductory organic chemistry. You&#8217;re welcome.<\/p>\n<p>This ends our two part discussion of optical activity, polarimetry, specific rotation, and optical purity.<\/p>\n<p>Questions or comments about this post? Leave one below!<\/p>\n<hr \/>\n<p>Thanks again to Matt for helping with this post.<strong>\u00a0<a href=\"https:\/\/masterorganic.wufoo.com\/forms\/q1yg3qx8076h7gx\/\">Hire Matt as your tutor!\u00a0<\/a><\/strong><\/p>\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\/2012\/05\/23\/whats-a-racemic-mixture\/\" class=\"\"><span>What\u2019s a Racemic Mixture?<\/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\/2015\/01\/13\/chiral-allenes-and-chiral-axes\/\" class=\"\"><span>Chiral Allenes And Chiral Axes<\/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\/2017\/02\/07\/optical-rotation-optical-activity-and-specific-rotation\/\" class=\"\"><span>Optical Rotation, Optical Activity, and Specific Rotation<\/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><\/ul><\/div>\n<p><a id=\"noteone\"><\/a><strong>Note 1.\u00a0<\/strong> This was proposed in 1848, about 25 years before Van&#8217;t Hoff proposed tetrahedral carbon. Pasteur&#8217;s work was one of the foundations on which Van&#8217;t Hoff made his proposal; a carbon with 4 different groups can only exist as two different enantiomers if the carbon is tetrahedral. It&#8217;s impossible if carbon is square planar.<\/p>\n<p><a id=\"notetwo\"><\/a><strong>Note 2. <\/strong>These situations frequently come about when using an enantioselective reaction on an achiral compound, such as the <a href=\"https:\/\/en.wikipedia.org\/wiki\/Sharpless_epoxidation\">epoxidation reaction<\/a> that won Barry Sharpless the 2001 <a href=\"https:\/\/pubs.rsc.org\/en\/content\/articlelanding\/2018\/sc\/c7sc04249c#!divAbstractts)\">Nobel Prize<\/a> (fittingly, this reaction employs the enantiomers of tartaric acid to impart\u00a0\u00a0&#8220;handedness&#8221; to the product). \u00a0Enzymes are likely a more familiar category of enantioselective catalysts: <a href=\"https:\/\/en.wikipedia.org\/wiki\/Baker's_yeast#Organic_synthesis\">Baker&#8217;s yeast <\/a>has been used\u00a0for the enantioselective reduction of ketones, for instance.<\/p>\n<p><a id=\"notethree\"><\/a><strong>Note 3. <\/strong>Optical rotation measurements (i.e. polarimetry) are actually an unreliable way to determine enantiomeric excess. There are three reasons.<\/p>\n<ul>\n<li>The optical rotation of the pure enantiomers may not be known<\/li>\n<li>Small amount of optically active impurities may cause the experiment to give drastically incorrect results [UPDATE: Like in the real-life example of <a href=\"https:\/\/pubs.rsc.org\/en\/content\/articlelanding\/2018\/sc\/c7sc04249c#!divAbstract\">Frondisin B<\/a>].<\/li>\n<li>Optical rotation doesn&#8217;t always have a linear relationship to enantiomeric excess like we&#8217;re claiming it does here. This is because of the <a href=\"http:\/\/www.readcube.com\/articles\/10.1002\/chir.22565\">Horeau Effect<\/a>.<\/li>\n<\/ul>\n<p>A more common way to measure enantiomeric excess is through HPLC or GC with a chiral stationary phase, or through the <a href=\"https:\/\/en.wikipedia.org\/wiki\/Mosher's_acid\">Mosher method<\/a>.<\/p>\n<hr \/>\n<h2><a id=\"quizzes\"><\/a>Quiz Yourself!<\/h2>\n<p><br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0932-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0933-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0934-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0874-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><\/p>\n","protected":false},"excerpt":{"rendered":"<p>All About Optical Purity and Enantiomeric Excess What is a racemic mixture? What is &#8220;optically active&#8221;, &#8220;optically inactive&#8221;, and &#8220;optically pure&#8221;. What do the terms, <\/p>\n","protected":false},"author":1,"featured_media":37392,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1413],"tags":[1185,1186,1168,1169],"post_folder":[],"class_list":["post-10487","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-stereochemistry-chirality","tag-enantiomeric-excess","tag-optical-purity","tag-optical-rotation","tag-specific-rotation"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Optical Purity and Enantiomeric Excess &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"Enantiomeric excess and optical purity; practice problems; what does &quot;optically pure&quot; mean, and how is it different from a racemic mixture? d- \/ l- and more\" \/>\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\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Optical Purity and Enantiomeric Excess &#8211; Master Organic Chemistry\" \/>\n<meta property=\"og:description\" content=\"Enantiomeric excess and optical purity; practice problems; what does &quot;optically pure&quot; mean, and how is it different from a racemic mixture? d- \/ l- and more\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.masterorganicchemistry.com\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/\" \/>\n<meta property=\"og:site_name\" content=\"Master Organic Chemistry\" \/>\n<meta property=\"article:publisher\" content=\"https:\/\/www.facebook.com\/Master-Organic-Chemistry-242610599108055\/\" \/>\n<meta property=\"article:published_time\" content=\"2017-02-25T00:02:01+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2026-05-07T00:36:56+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2017\/02\/0-summary-of-optical-rotation-enantiomeric-excess-optical-purity.gif\" \/>\n\t<meta property=\"og:image:width\" content=\"938\" \/>\n\t<meta property=\"og:image:height\" content=\"802\" \/>\n\t<meta property=\"og:image:type\" content=\"image\/gif\" \/>\n<meta name=\"author\" content=\"James Ashenhurst\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"James Ashenhurst\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"13 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\\\/\\\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2017\\\/02\\\/24\\\/optical-purity-and-enantiomeric-excess\\\/#article\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2017\\\/02\\\/24\\\/optical-purity-and-enantiomeric-excess\\\/\"},\"author\":{\"name\":\"James Ashenhurst\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/person\\\/78d83ec7d02b4b7365bade2cedaef80c\"},\"headline\":\"Optical Purity and Enantiomeric Excess\",\"datePublished\":\"2017-02-25T00:02:01+00:00\",\"dateModified\":\"2026-05-07T00:36:56+00:00\",\"mainEntityOfPage\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2017\\\/02\\\/24\\\/optical-purity-and-enantiomeric-excess\\\/\"},\"wordCount\":1978,\"commentCount\":6,\"publisher\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#organization\"},\"image\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2017\\\/02\\\/24\\\/optical-purity-and-enantiomeric-excess\\\/#primaryimage\"},\"thumbnailUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2017\\\/02\\\/0-summary-of-optical-rotation-enantiomeric-excess-optical-purity.gif\",\"keywords\":[\"enantiomeric excess\",\"optical purity\",\"optical rotation\",\"specific rotation\"],\"articleSection\":[\"Stereochemistry and Chirality\"],\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"CommentAction\",\"name\":\"Comment\",\"target\":[\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2017\\\/02\\\/24\\\/optical-purity-and-enantiomeric-excess\\\/#respond\"]}]},{\"@type\":\"WebPage\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2017\\\/02\\\/24\\\/optical-purity-and-enantiomeric-excess\\\/\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2017\\\/02\\\/24\\\/optical-purity-and-enantiomeric-excess\\\/\",\"name\":\"Optical Purity and Enantiomeric Excess &#8211; Master Organic Chemistry\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#website\"},\"primaryImageOfPage\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2017\\\/02\\\/24\\\/optical-purity-and-enantiomeric-excess\\\/#primaryimage\"},\"image\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2017\\\/02\\\/24\\\/optical-purity-and-enantiomeric-excess\\\/#primaryimage\"},\"thumbnailUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2017\\\/02\\\/0-summary-of-optical-rotation-enantiomeric-excess-optical-purity.gif\",\"datePublished\":\"2017-02-25T00:02:01+00:00\",\"dateModified\":\"2026-05-07T00:36:56+00:00\",\"description\":\"Enantiomeric excess and optical purity; practice problems; what does \\\"optically pure\\\" mean, and how is it different from a racemic mixture? d- \\\/ l- and more\",\"breadcrumb\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2017\\\/02\\\/24\\\/optical-purity-and-enantiomeric-excess\\\/#breadcrumb\"},\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"ReadAction\",\"target\":[\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2017\\\/02\\\/24\\\/optical-purity-and-enantiomeric-excess\\\/\"]}]},{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2017\\\/02\\\/24\\\/optical-purity-and-enantiomeric-excess\\\/#primaryimage\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2017\\\/02\\\/0-summary-of-optical-rotation-enantiomeric-excess-optical-purity.gif\",\"contentUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2017\\\/02\\\/0-summary-of-optical-rotation-enantiomeric-excess-optical-purity.gif\",\"width\":938,\"height\":802,\"caption\":\"summary of optical rotation enantiomeric excess optical purity\"},{\"@type\":\"BreadcrumbList\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2017\\\/02\\\/24\\\/optical-purity-and-enantiomeric-excess\\\/#breadcrumb\",\"itemListElement\":[{\"@type\":\"ListItem\",\"position\":1,\"name\":\"Home\",\"item\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/\"},{\"@type\":\"ListItem\",\"position\":2,\"name\":\"Optical Purity and Enantiomeric Excess\"}]},{\"@type\":\"WebSite\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#website\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/\",\"name\":\"Master Organic Chemistry\",\"description\":\"\",\"publisher\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#organization\"},\"potentialAction\":[{\"@type\":\"SearchAction\",\"target\":{\"@type\":\"EntryPoint\",\"urlTemplate\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/?s={search_term_string}\"},\"query-input\":{\"@type\":\"PropertyValueSpecification\",\"valueRequired\":true,\"valueName\":\"search_term_string\"}}],\"inLanguage\":\"en-US\"},{\"@type\":\"Organization\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#organization\",\"name\":\"Master Organic Chemistry\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/\",\"logo\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/logo\\\/image\\\/\",\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2019\\\/04\\\/cutmypic.png\",\"contentUrl\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/wp-content\\\/uploads\\\/2019\\\/04\\\/cutmypic.png\",\"width\":225,\"height\":225,\"caption\":\"Master Organic Chemistry\"},\"image\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/logo\\\/image\\\/\"},\"sameAs\":[\"https:\\\/\\\/www.facebook.com\\\/Master-Organic-Chemistry-242610599108055\\\/\"]},{\"@type\":\"Person\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/person\\\/78d83ec7d02b4b7365bade2cedaef80c\",\"name\":\"James Ashenhurst\",\"image\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\\\/\\\/secure.gravatar.com\\\/avatar\\\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g\",\"url\":\"https:\\\/\\\/secure.gravatar.com\\\/avatar\\\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g\",\"contentUrl\":\"https:\\\/\\\/secure.gravatar.com\\\/avatar\\\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g\",\"caption\":\"James Ashenhurst\"},\"description\":\"Ph.D. 2006, McGill University (James L. Gleason). Postdoctoral Associate, 2008-2010, Massachusetts Institute of Technology (M. Movassaghi). Founder, Master Organic Chemistry, 2010-present.\",\"sameAs\":[\"https:\\\/\\\/www.masterorganicchemistry.com\\\/about\\\/\"],\"url\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/author\\\/james\\\/\"}]}<\/script>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Optical Purity and Enantiomeric Excess &#8211; Master Organic Chemistry","description":"Enantiomeric excess and optical purity; practice problems; what does \"optically pure\" mean, and how is it different from a racemic mixture? d- \/ l- and more","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/www.masterorganicchemistry.com\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/","og_locale":"en_US","og_type":"article","og_title":"Optical Purity and Enantiomeric Excess &#8211; Master Organic Chemistry","og_description":"Enantiomeric excess and optical purity; practice problems; what does \"optically pure\" mean, and how is it different from a racemic mixture? d- \/ l- and more","og_url":"https:\/\/www.masterorganicchemistry.com\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/","og_site_name":"Master Organic Chemistry","article_publisher":"https:\/\/www.facebook.com\/Master-Organic-Chemistry-242610599108055\/","article_published_time":"2017-02-25T00:02:01+00:00","article_modified_time":"2026-05-07T00:36:56+00:00","og_image":[{"width":938,"height":802,"url":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2017\/02\/0-summary-of-optical-rotation-enantiomeric-excess-optical-purity.gif","type":"image\/gif"}],"author":"James Ashenhurst","twitter_card":"summary_large_image","twitter_misc":{"Written by":"James Ashenhurst","Est. reading time":"13 minutes"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"Article","@id":"https:\/\/www.masterorganicchemistry.com\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/#article","isPartOf":{"@id":"https:\/\/www.masterorganicchemistry.com\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/"},"author":{"name":"James Ashenhurst","@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/person\/78d83ec7d02b4b7365bade2cedaef80c"},"headline":"Optical Purity and Enantiomeric Excess","datePublished":"2017-02-25T00:02:01+00:00","dateModified":"2026-05-07T00:36:56+00:00","mainEntityOfPage":{"@id":"https:\/\/www.masterorganicchemistry.com\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/"},"wordCount":1978,"commentCount":6,"publisher":{"@id":"https:\/\/www.masterorganicchemistry.com\/#organization"},"image":{"@id":"https:\/\/www.masterorganicchemistry.com\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/#primaryimage"},"thumbnailUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2017\/02\/0-summary-of-optical-rotation-enantiomeric-excess-optical-purity.gif","keywords":["enantiomeric excess","optical purity","optical rotation","specific rotation"],"articleSection":["Stereochemistry and Chirality"],"inLanguage":"en-US","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.masterorganicchemistry.com\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.masterorganicchemistry.com\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/","url":"https:\/\/www.masterorganicchemistry.com\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/","name":"Optical Purity and Enantiomeric Excess &#8211; Master Organic Chemistry","isPartOf":{"@id":"https:\/\/www.masterorganicchemistry.com\/#website"},"primaryImageOfPage":{"@id":"https:\/\/www.masterorganicchemistry.com\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/#primaryimage"},"image":{"@id":"https:\/\/www.masterorganicchemistry.com\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/#primaryimage"},"thumbnailUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2017\/02\/0-summary-of-optical-rotation-enantiomeric-excess-optical-purity.gif","datePublished":"2017-02-25T00:02:01+00:00","dateModified":"2026-05-07T00:36:56+00:00","description":"Enantiomeric excess and optical purity; practice problems; what does \"optically pure\" mean, and how is it different from a racemic mixture? d- \/ l- and more","breadcrumb":{"@id":"https:\/\/www.masterorganicchemistry.com\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/#breadcrumb"},"inLanguage":"en-US","potentialAction":[{"@type":"ReadAction","target":["https:\/\/www.masterorganicchemistry.com\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/"]}]},{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.masterorganicchemistry.com\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/#primaryimage","url":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2017\/02\/0-summary-of-optical-rotation-enantiomeric-excess-optical-purity.gif","contentUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2017\/02\/0-summary-of-optical-rotation-enantiomeric-excess-optical-purity.gif","width":938,"height":802,"caption":"summary of optical rotation enantiomeric excess optical purity"},{"@type":"BreadcrumbList","@id":"https:\/\/www.masterorganicchemistry.com\/2017\/02\/24\/optical-purity-and-enantiomeric-excess\/#breadcrumb","itemListElement":[{"@type":"ListItem","position":1,"name":"Home","item":"https:\/\/www.masterorganicchemistry.com\/"},{"@type":"ListItem","position":2,"name":"Optical Purity and Enantiomeric Excess"}]},{"@type":"WebSite","@id":"https:\/\/www.masterorganicchemistry.com\/#website","url":"https:\/\/www.masterorganicchemistry.com\/","name":"Master Organic Chemistry","description":"","publisher":{"@id":"https:\/\/www.masterorganicchemistry.com\/#organization"},"potentialAction":[{"@type":"SearchAction","target":{"@type":"EntryPoint","urlTemplate":"https:\/\/www.masterorganicchemistry.com\/?s={search_term_string}"},"query-input":{"@type":"PropertyValueSpecification","valueRequired":true,"valueName":"search_term_string"}}],"inLanguage":"en-US"},{"@type":"Organization","@id":"https:\/\/www.masterorganicchemistry.com\/#organization","name":"Master Organic Chemistry","url":"https:\/\/www.masterorganicchemistry.com\/","logo":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/logo\/image\/","url":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/04\/cutmypic.png","contentUrl":"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/04\/cutmypic.png","width":225,"height":225,"caption":"Master Organic Chemistry"},"image":{"@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/logo\/image\/"},"sameAs":["https:\/\/www.facebook.com\/Master-Organic-Chemistry-242610599108055\/"]},{"@type":"Person","@id":"https:\/\/www.masterorganicchemistry.com\/#\/schema\/person\/78d83ec7d02b4b7365bade2cedaef80c","name":"James Ashenhurst","image":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/secure.gravatar.com\/avatar\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g","contentUrl":"https:\/\/secure.gravatar.com\/avatar\/f9e9df435875e5e6b0bdff6b8522a7279d5717644b3efa7299da22c837bf9fcf?s=96&d=retro&r=g","caption":"James Ashenhurst"},"description":"Ph.D. 2006, McGill University (James L. Gleason). Postdoctoral Associate, 2008-2010, Massachusetts Institute of Technology (M. Movassaghi). Founder, Master Organic Chemistry, 2010-present.","sameAs":["https:\/\/www.masterorganicchemistry.com\/about\/"],"url":"https:\/\/www.masterorganicchemistry.com\/author\/james\/"}]}},"_links":{"self":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/posts\/10487","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/comments?post=10487"}],"version-history":[{"count":0,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/posts\/10487\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/media\/37392"}],"wp:attachment":[{"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/media?parent=10487"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/categories?post=10487"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/tags?post=10487"},{"taxonomy":"post_folder","embeddable":true,"href":"https:\/\/www.masterorganicchemistry.com\/wp-json\/wp\/v2\/post_folder?post=10487"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}