{"id":12003,"date":"2018-10-22T06:00:16","date_gmt":"2018-10-22T10:00:16","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=12003"},"modified":"2026-04-22T10:08:25","modified_gmt":"2026-04-22T15:08:25","slug":"aromatic-synthesis-2-polarity-reversal","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2018\/10\/22\/aromatic-synthesis-2-polarity-reversal\/","title":{"rendered":"Synthesis of Benzene Derivatives (2) &#8211; Polarity Reversal"},"content":{"rendered":"<p><strong>Synthesis of Benzene Derivatives: Converting <em>ortho-,para-<\/em> directors into <em>meta-<\/em> directors and vice versa.<\/strong><\/p>\n<p>In planning the synthesis of simple benzene derivatives and other aromatic compounds, it&#8217;s vital to know some tricks for changing <em>ortho-, para-\u00a0<\/em>directors into\u00a0<em>meta-<\/em> directors, and vice versa!<\/p>\n<p>In this article we go into detail on how to do these &#8220;reversals of polarity&#8221;:<\/p>\n<ul>\n<li>Reduction of nitro groups (NO<sub>2<\/sub>) to amines converts a meta director to an <em>ortho<\/em>-, <em>para<\/em>&#8211; director<\/li>\n<li>Reduction of ketones (C=O) to alkanes converts a meta director to an <em>ortho<\/em>-, <em>para<\/em>&#8211; director<\/li>\n<li>The Baeyer-Villiger reaction converts a ketone (<em>meta-<\/em> director) to an ester (<em>ortho<\/em>-, <em>para<\/em>&#8211; director)<\/li>\n<li>Benzylic oxidation with KMnO<sub>4<\/sub> converts an <em>ortho<\/em>-, <em>para<\/em>&#8211; director to a\u00a0<em>meta-<\/em> director<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-16047\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/0-summary-of-polarity-reversal-for-aromatic-reactions-convert-meta-directors-to-ortho-para-or-vice-versa.gif\" alt=\"summary of polarity reversal for aromatic reactions convert meta directors to ortho para or vice versa\" width=\"640\" height=\"380\" \/><\/p>\n<hr \/>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Reminder: The &#8220;Order of Operations&#8221; Is Important<\/a><\/li>\n<li><a href=\"#two\">What Do We Do When Directing Groups Don&#8217;t Direct The &#8220;Right Way&#8221; ?<\/a><\/li>\n<li><a href=\"#three\"><em>Ortho-, Para-\u00a0<\/em>Directors From\u00a0<em>Meta-\u00a0<\/em>Directors: 3 Examples<\/a><\/li>\n<li><a href=\"#four\"><em>Meta-\u00a0<\/em>Directors From\u00a0<em>Ortho-, Para-\u00a0<\/em>Directors<\/a><\/li>\n<li><a href=\"#five\">Summary: Synthesis of Benzene Derivatives &#8211; Polarity Reversal<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quizzes\">Quiz Yourself!<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><a id=\"one\"><\/a>1. Reminder: The &#8220;Order of Operations&#8221; Is Important<\/h2>\n<p>Last time we talked about the importance of choosing the correct &#8220;order of operations&#8221; in the synthesis of aromatic compounds\u00a0<span style=\"color: #993366;\"><em>[See post: <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/?p=11963&amp;preview=true\">Aromatic Synthesis (1): Order of Operations<\/a>]. <\/em><\/span><\/p>\n<p>Key points:<\/p>\n<p>If you&#8217;re planning a synthesis of a disubstituted benzene derivative containing an <em>ortho-, para-\u00a0<\/em>director and a\u00a0<em>meta<\/em>&#8211; director, you need to choose the order of operations wisely:<\/p>\n<ul>\n<li><strong>To obtain the\u00a0<em>para<\/em>&#8211; (or\u00a0<em>ortho- <\/em>) product &#8212;-&gt; install the\u00a0<em>ortho- , para-\u00a0<\/em>director first<\/strong><\/li>\n<li><strong>To obtain the\u00a0<em>meta<\/em>&#8211; product &#8212;-&gt; install the\u00a0<em>meta-<\/em> director first<\/strong><\/li>\n<\/ul>\n<p>Alright.\u00a0 Now let&#8217;s throw a curveball.<\/p>\n<h2><a id=\"two\"><\/a>2. What Do We Do When Directing Groups Don&#8217;t Direct The &#8220;Right Way&#8221;?<\/h2>\n<p>How would you synthesize <em>this<\/em> molecule, which has two\u00a0<em>ortho-, para-\u00a0<\/em>directors oriented\u00a0<em>meta<\/em>&#8211; to each other?<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-16048\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-synthesis-of-meta-chloropentylbenzene-how-to-do-it.gif\" alt=\"synthesis of meta chloropentylbenzene how to do it\" width=\"600\" height=\"270\" \/><\/p>\n<p>No two-step sequence of electrophilic aromatic substitution reactions will give you this product!<\/p>\n<p><em>So what do we do?<\/em><\/p>\n<p>Not to worry. There&#8217;s a whole other bag of tricks we haven&#8217;t used yet &#8211;\u00a0<strong>reactions that modify aromatic substituents &#8211;\u00a0<\/strong>that will provide us with the solution to problems like this one.<\/p>\n<p>The key is to combine our knowledge of &#8220;order of operations&#8221;\u00a0 with reactions that change\u00a0<em>meta<\/em>&#8211; directors to\u00a0<em>ortho-, para-\u00a0<\/em>directors (or vice versa).<\/p>\n<p>I like to think of this as a &#8220;<strong>polarity reversal<\/strong>&#8221;\u00a0 &#8211; changing the nature of the substituent from an electron-acceptor (<em>meta-<\/em> director) to an electron-donor (<em>ortho-, para-\u00a0<\/em>director) or vice-versa.<\/p>\n<h2><strong><a id=\"three\"><\/a>3.<em> Ortho-, Para<\/em>&#8211; Directors From <em>Meta<\/em>&#8211; Directors: 3 Examples<\/strong><\/h2>\n<p>We&#8217;ve learned three key classes of reactions that modify aromatic substituents in a way that convert\u00a0<em>meta<\/em>&#8211; directors to\u00a0<em>ortho-, para-\u00a0<\/em>directors:<\/p>\n<ul>\n<li>reduction of nitro groups (NO<sub>2<\/sub>) to amines (NH<sub>2<\/sub>) using Pd-C\/H<sub>2<\/sub> , Zn \/ HCl and other methods.[<em><a href=\"https:\/\/www.masterorganicchemistry.com\/?p=11949&amp;preview=true\">See post<\/a>]<\/em><\/li>\n<li>reduction of ketones to alkyl groups using the Wolff-Kishner, Clemmensen, or other methods [<em><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/08\/27\/the-wolff-kishner-clemmensen-and-other-sidechain-reductions\/\">See post<\/a>]<\/em><\/li>\n<li>Baeyer-Villiger oxidation of ketones to esters using peroxyacids (e.g.\u00a0<em>m<\/em>-CPBA).[<em><a href=\"https:\/\/www.masterorganicchemistry.com\/?p=11949&amp;preview=true\">See post<\/a>]<\/em><\/li>\n<\/ul>\n<p><img decoding=\"async\" class=\"alignnone wp-image-16049\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-examples-of-converting-meta-directors-to-ortho-para-directors-reduction-of-nitro-to-nh2-reduction-of-ketones-to-alkyl-baeyer-villiger-oxidation.gif\" alt=\"examples of converting meta directors to ortho para directors reduction of nitro to nh2 reduction of ketones to alkyl baeyer villiger oxidation\" width=\"600\" height=\"586\" \/><\/p>\n<p>Having these reactions available to us greatly expands the number of products we can build from benzene.<\/p>\n<p>How so?<\/p>\n<p><strong>Let&#8217;s think backwards<\/strong>.\u00a0 Having access to these reactions means that if there is an amine in a product we wish to make, it can be obtained from reduction of a nitro group.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-16050\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-aromatic-synthesis-working-backwards-from-amines-to-nitro-groups-to-benzene.gif\" alt=\"aromatic synthesis working backwards from amines to nitro groups to benzene\" width=\"600\" height=\"244\" \/><\/p>\n<p><span style=\"color: #993366;\"><em>(The specific reactions to use in the forward direction are essentially equivalent, for our purposes).\u00a0 We can use a reducing metal like Zn, Fe, or Sn with acid, or catalytic hydrogenation over palladium or platinum.\u00a0<\/em><\/span><\/p>\n<p>The nitro group, in turn, can be installed through electrophilic aromatic substitution (HNO<sub>3<\/sub> + H<sub>2<\/sub>SO<sub>4<\/sub>).<\/p>\n<p>We can apply the same backwards-looking process toward alkyl groups. While alkyl groups\u00a0<em>can<\/em> be installed directly using Friedel-Crafts alkylation, remember that carbocation rearrangements can occur with longer-chain primary alkyl halides. Previously, we saw that long alkyl chains can be installed by performing a Friedel-Crafts acylation first, followed by reduction of the ketone<em><span style=\"color: #993366;\"> (a.k.a. &#8220;The Great Friedel-Crafts Workaround&#8221;)<\/span>.\u00a0<\/em>[<em>See post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/05\/17\/friedel-crafts-alkylation-acylation\/\">The Friedel-Crafts Reactions<\/a><\/em>]<\/p>\n<p>So any time you see an alkyl group in a target molecule, by all means consider the (straightforward) Friedel-Crafts alkylation, but also take a moment to think about how it could be installed through working backwards to a ketone.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-16051\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-aromatic-synthesis-working-backwards-from-alkyl-groups-to-ketones-to-benzene.gif\" alt=\"aromatic synthesis working backwards from alkyl groups to ketones to benzene\" width=\"600\" height=\"241\" \/><\/p>\n<p>Finally, working backwards from an O-C(O)R group also gets us back to a ketone, via the Baeyer-Villger, and the ketone can be made through Friedel-Crafts acylation.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-16052\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-working-backwards-acyloxy-to-ketone-to-benzene-baeyer-villiger.gif\" alt=\"working backwards acyloxy to ketone to benzene baeyer villiger\" width=\"600\" height=\"312\" \/><\/p>\n<p>Now, back to our regularly scheduled problem.<\/p>\n<p>Clearly we can&#8217;t build this molecule directly through two consecutive electrophilic aromatic substitution reactions.<\/p>\n<p>But what if we work backwards from the alkyl group to the ketone? That gives us a ketone &#8211; a\u00a0 <em>meta-\u00a0<\/em>director. Now a solution becomes clear\u00a0 (as long as we get our order of operations correct)!<\/p>\n<p>Since we want the\u00a0<em>meta<\/em>&#8211; product, we start by installing the\u00a0<em>meta-\u00a0<\/em>director through a Friedel-Crafts acylation. We then chlorinate (Cl<sub>2<\/sub> \/ FeCl<sub>3<\/sub>) and finally reduce the ketone to get our final product.<\/p>\n<p><a href=\"\" class=\"custom-tooltip\" data-image=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2018\/10\/S1-first-problem-e1557939927831.png\" data-link=\"\" data-title=\"\" data-text=\"\">Hover for an example of using the Clemmensen in the forward direction <\/a>(<a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2018\/10\/S1-first-problem-e1557939927831.png\">link to image)<\/a><\/p>\n<p>For more practice, try working on these examples which require similar reasoning:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-16053\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-examples-of-synthesis-of-aromatic-molecules-from-benzene.gif\" alt=\"examples of synthesis of aromatic molecules from benzene\" width=\"600\" height=\"205\" \/><\/p>\n<p><em>[more discussion of these problems in <a href=\"#notetwo\">Note 2<\/a>]<\/em><\/p>\n<h2><strong><a id=\"four\"><\/a>4.<\/strong><em><strong> Meta- <\/strong><\/em><strong>Directors <\/strong><strong>From <\/strong><em><strong>Ortho- , Para- <\/strong><\/em><strong>Directors<\/strong><\/h2>\n<p>Let&#8217;s look at a different type of problem. Below, we have a carboxylic acid (<em>meta-<\/em> director)\u00a0<em>para<\/em> to a nitro group (another\u00a0<em>meta<\/em> director). So how can we design a synthesis that gets these two\u00a0<em>meta-\u00a0<\/em>directors\u00a0<em>para<\/em>&#8211; to each other?<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-16054\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-how-to-synthesize-para-nitro-benzoic-acid-from-benzene-two-meta-directors-para-to-each-other.gif\" alt=\"how to synthesize para nitro benzoic acid from benzene two meta directors para to each other\" width=\"600\" height=\"222\" \/><\/p>\n<p>There&#8217;s one reaction we&#8217;ve previously covered that converts an\u00a0<em>ortho-, para-\u00a0<\/em>director to a\u00a0<em>meta<\/em>&#8211; director:<\/p>\n<ul>\n<li>oxidation of alkyl groups with KMnO<sub>4\u00a0<\/sub> to give carboxylic acids. [<em>see post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/06\/13\/reactions-on-the-benzylic-carbon-bromination-and-oxidation\/\">Reactions on the &#8220;Benzylic&#8221; Carbon<\/a>]<\/em><\/li>\n<\/ul>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-16055\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/8-aromatic-synthesis-working-backwards-carboxylic-acids-from-alkylbenzenes.gif\" alt=\"aromatic synthesis working backwards carboxylic acids from alkylbenzenes\" width=\"600\" height=\"244\" \/><\/p>\n<p>Working backwards from a carboxylic acid gives us an alkyl group, which could be obtained through Friedel-Crafts alkylation.<\/p>\n<p><span style=\"color: #993366;\"><em>[Note: although this doesn&#8217;t strictly convert an ortho-, para- director to a meta- director,\u00a0 it&#8217;s also worth looking at <a style=\"color: #993366;\" href=\"#two\">benzylic bromination<\/a> as another route to meta- directors, since alkyl halides are so versatile. We&#8217;ll cover this in <a style=\"color: #993366;\" href=\"#noteone\">Note 1<\/a> ]<\/em><\/span><\/p>\n<p>Going back to our example, we see that working backwards from the carboxylic acid gives us an alkyl group (so long as it&#8217;s not <em>t<\/em>-butyl, the exact identity isn&#8217;t important, since KMnO<sub>4<\/sub> chews up all alkyl groups with at least one benzylic C-H bond to give carboxylic acids).<\/p>\n<p>Synthesis of this <em>para<\/em>-disubstituted molecule requires that we start with the Friedel-Crafts alkylation, followed by nitration.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-16056\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/9-working-backwards-paranitrobenzoic-acid-to-para-nitroethylbenzene-kmno4-oxidation.gif\" alt=\"working backwards paranitrobenzoic acid to para nitroethylbenzene kmno4 oxidation\" width=\"600\" height=\"295\" \/><\/p>\n<p><span style=\"color: #993366;\"><em>(This is by no means the only way to do it! One of the fun parts about synthesis is that there are multiple ways to approach the same problem!) (<a style=\"color: #993366;\" href=\"#notethree\">Note 3<\/a>)<\/em><\/span><\/p>\n<h2><strong><a id=\"five\"><\/a>5. Summary: Synthesis of Benzene Derivatives &#8211; Polarity Reversal<\/strong><\/h2>\n<p>Planning the right &#8220;order of operations&#8221; with reactions that &#8220;reverse the polarity&#8221; of aromatic side chains will allow you to synthesize most of the molecules you will encounter in synthesis problems.<\/p>\n<p>We didn&#8217;t go into the synthesis of trisubstituted molecules, but the same strategies also apply,\u00a0 along with the key principle\u00a0&#8220;<a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/03\/19\/eas-disubstituted-benzenes\/\">the strongest donor wins<\/a>&#8221;<\/p>\n<p><span style=\"color: #993366;\"><em>(Additionally, we haven&#8217;t really considered nucleophilic substitution reactions here,\u00a0 but they could concievably be worked in too.\u00a0 In synthesis everything is fair game unless you&#8217;re told otherwise).\u00a0<\/em><\/span><\/p>\n<p>Before we do a few practice problems, there&#8217;s one last trick to cover.<\/p>\n<p>What if you only want the\u00a0<em>ortho<\/em> products and not the\u00a0<em>para<\/em>?<\/p>\n<p>In the next post, we&#8217;ll show a strategy for doing this, using &#8220;blocking groups&#8221;.<\/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\/2018\/10\/15\/aromatic-synthesis-1-order-of-operations\/\" class=\"\"><span>Aromatic Synthesis (1) \u2013 \u201cOrder Of Operations\u201d<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/11\/26\/sulfonyl-blocking-groups-aromatic-synthesis\/\" class=\"\"><span>Aromatic Synthesis (3) \u2013 Sulfonyl Blocking Groups<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/05\/17\/friedel-crafts-alkylation-acylation\/\" class=\"\"><span>EAS Reactions (3) \u2013 Friedel-Crafts Acylation and Friedel-Crafts Alkylation<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/08\/27\/the-wolff-kishner-clemmensen-and-other-sidechain-reductions\/\" class=\"\"><span>The Wolff-Kishner, Clemmensen, And Other Carbonyl Reductions<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/06\/13\/reactions-on-the-benzylic-carbon-bromination-and-oxidation\/\" class=\"\"><span>Reactions on the \u201cBenzylic\u201d Carbon: Bromination And Oxidation<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/11\/19\/synthesis-7-reaction-map-of-benzene-and-related-aromatic-compounds\/\" class=\"\"><span>Synthesis (7): Reaction Map of Benzene and Related Aromatic Compounds<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/organic-chemistry-practice-problems\/aromatic-reactions-and-synthesis-practice\/\" class=\"\"><span>Aromatic Reactions and Synthesis Practice (MOC Membership)<\/span><\/a><\/li><\/ul><\/div>\n<p><strong><a id=\"noteone\"><\/a>Note 1. Benzylic Bromination<\/strong><\/p>\n<p>Benzylic bromination can be a useful precursor to\u00a0<em>meta-\u00a0<\/em>directors, although somewhat longer sequences of reactions are usually required to get to the desired product.<\/p>\n<p>Here&#8217;s an example.\u00a0 How do you synthesize this molecule with two\u00a0<em>meta-\u00a0<\/em>directors oriented\u00a0<em>para-<\/em> to each other??<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-16057\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F1-how-to-synthesize-para-nitroacetophenone.gif\" alt=\"how to synthesize para nitroacetophenone\" width=\"600\" height=\"209\" \/><\/p>\n<p>One way to do it would be to use a reaction that oxidizes an alkyl group to a ketone.\u00a0 <em>One little problem: we haven&#8217;t learned how to do that directly.<\/em><\/p>\n<p>However, we have learned how to convert &#8220;benzylic&#8221; alkyl groups into alkyl halides. And if there&#8217;s one thing you learn in Org 1, it&#8217;s that alkyl halides can undergo a ton of different reactions. [<span style=\"color: #993366;\"><em><a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2014\/01\/10\/synthesis-3-reactions-of-alkyl-halides\/\">this post<\/a> has a &#8220;reaction map&#8221; for alkyl halides<\/em><\/span>]<\/p>\n<ul>\n<li>One way to get to the ketone from the alkyl bromide would be to perform an S<sub>N<\/sub>2 of the benzyl bromide with hydroxide (in a polar aprotic solvent) to give an alcohol, which could be oxidized to a ketone.<\/li>\n<li>Another way would be to eliminate the halide (E2) with strong base to give an alkene, followed by hydration (oxymercuration or H<sub>3<\/sub>O+) to give an alcohol, which could be oxidized similarly.<\/li>\n<\/ul>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-16058\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F2-working-backwards-from-benzylic-halides-to-alkylbenzenes-to-benzene-benzylic-bromination.gif\" alt=\"working backwards from benzylic halides to alkylbenzenes to benzene benzylic bromination\" width=\"600\" height=\"688\" \/><\/p>\n<p>The ketone is just one of other possible examples. As the pathways below try to show, alkyl halides are a gateway not only to the many compounds possible from nucleophilic substitution reactions, but also to those arising from reactions of alkenes and alcohols.<\/p>\n<p><strong><a id=\"notetwo\"><\/a>Note 2. Exercises from above (Try working these on your own first!)<\/strong><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-16059\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F3-synthesis-examples-worked-examples.gif\" alt=\"synthesis examples worked examples\" width=\"600\" height=\"209\" \/><\/p>\n<p><strong>Worked example #1 .<\/strong><\/p>\n<p><a href=\"\" class=\"custom-tooltip\" data-image=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/Supp-2-synthesis-beginning-with-friedel-crats-acylation-then-nitration-then-baeyer-villiger-then-reduction-then-acylation.gif\" data-link=\"\" data-title=\"\" data-text=\"\">Hover to see one possible approach <\/a><a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/Supp-2-synthesis-beginning-with-friedel-crats-acylation-then-nitration-then-baeyer-villiger-then-reduction-then-acylation.gif\"> (link to larger image)<\/a><\/p>\n<p><strong>Worked example #2<\/strong><\/p>\n<p><a href=\"\" class=\"custom-tooltip\" data-image=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/Supp-3-two-possible-approaches-to-meta-aminopropylbenzene.gif\" data-link=\"\" data-title=\"\" data-text=\"\">Hover to see one possible approach<\/a> <a href=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/Supp-3-two-possible-approaches-to-meta-aminopropylbenzene.gif\">(link to larger image)<\/a><\/p>\n<p><strong><a id=\"notethree\"><\/a>Note 3<\/strong> &#8211; For instance another way to do it (that doesn&#8217;t involve EAS) would be to make the carboxylic acid through reaction of a Grignard with CO<sub>2<\/sub>. The Grignard would come from Br or Cl, which are\u00a0<em>ortho-, para-\u00a0<\/em>directors. So: bromination, nitration, Grignard formation, then add CO<sub>2<\/sub>.<\/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\/0553-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\/0554-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\/0555-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\/0556-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>Synthesis of Benzene Derivatives: Converting ortho-,para- directors into meta- directors and vice versa. In planning the synthesis of simple benzene derivatives and other aromatic compounds, <\/p>\n","protected":false},"author":1,"featured_media":16047,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1297],"tags":[312,175,319,321,1368,1377,823,352],"post_folder":[],"class_list":["post-12003","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-aromatic-reactions","tag-aromatics","tag-baeyer-villiger","tag-electrophilic-aromatic-substitution","tag-friedel-crafts","tag-nitro","tag-order-of-operations","tag-retrosynthesis","tag-synthesis"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Turning Ortho-Para Directors Into Meta Directors (and vice versa)<\/title>\n<meta name=\"description\" content=\"In planning the synthesis of simple benzene derivatives, it&#039;s vital to know some tricks for changing\u00a0ortho-, para-\u00a0directors into\u00a0meta- directors, or vice-versa.\" \/>\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\/2018\/10\/22\/aromatic-synthesis-2-polarity-reversal\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Turning Ortho-Para Directors Into Meta Directors (and vice versa)\" \/>\n<meta property=\"og:description\" content=\"In planning the synthesis of simple benzene derivatives, it&#039;s vital to know some tricks for changing\u00a0ortho-, para-\u00a0directors into\u00a0meta- directors, or vice-versa.\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.masterorganicchemistry.com\/2018\/10\/22\/aromatic-synthesis-2-polarity-reversal\/\" \/>\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=\"2018-10-22T10:00:16+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2026-04-22T15:08:25+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/0-summary-of-polarity-reversal-for-aromatic-reactions-convert-meta-directors-to-ortho-para-or-vice-versa.gif\" \/>\n\t<meta property=\"og:image:width\" content=\"1010\" \/>\n\t<meta property=\"og:image:height\" content=\"600\" \/>\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=\"10 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\\\/\\\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2018\\\/10\\\/22\\\/aromatic-synthesis-2-polarity-reversal\\\/#article\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/2018\\\/10\\\/22\\\/aromatic-synthesis-2-polarity-reversal\\\/\"},\"author\":{\"name\":\"James Ashenhurst\",\"@id\":\"https:\\\/\\\/www.masterorganicchemistry.com\\\/#\\\/schema\\\/person\\\/78d83ec7d02b4b7365bade2cedaef80c\"},\"headline\":\"Synthesis of Benzene Derivatives (2) &#8211; 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