{"id":11599,"date":"2018-05-17T08:00:01","date_gmt":"2018-05-17T12:00:01","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=11599"},"modified":"2026-04-18T04:59:29","modified_gmt":"2026-04-18T09:59:29","slug":"friedel-crafts-alkylation-acylation","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2018\/05\/17\/friedel-crafts-alkylation-acylation\/","title":{"rendered":"EAS Reactions (3) &#8211; Friedel-Crafts Acylation and Friedel-Crafts Alkylation"},"content":{"rendered":"<p><strong>Friedel Crafts Alkylation and Acylation<\/strong><\/p>\n<ul>\n<li>Aromatic rings will form C-C bonds when treated with alkyl or acyl halides in the presence of a strong Lewis acid (e.g. AlCl<sub>3<\/sub>). These are known as <strong>Friedel Crafts<\/strong> reactions and are examples of <strong>electrophilic aromatic substitution reactions<\/strong>.<\/li>\n<li>The Lewis acid coordinates to a lone pair on the halogen, making the halogen a better leaving group.<\/li>\n<li>In Friedel-Crafts alkylation, an alkyl halide treated with a Lewis acid results in a carbocation electrophile <span style=\"color: #993366;\"><em>(or a species very similar to a carbocation)\u00a0<\/em><span style=\"color: #000000;\">that is then attacked by the aromatic ring.\u00a0<\/span><\/span><\/li>\n<li><strong>Carbocation rearrangements can occur<\/strong> if they result in a more stable carbocation!<\/li>\n<li>Friedel-Crafts acylation is performed with acyl halides and Lewis acids. <strong>No rearrangements<\/strong> are observed.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-15927\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/0-summary-of-friedel-crafts-alkylation-and-acylation-what-bonds-form-and-break-limitations-and-substrates.gif\" alt=\"summary of friedel crafts alkylation and acylation what bonds form and break limitations and substrates\" width=\"600\" height=\"559\" \/><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Quick Recap on Electrophilic Aromatic Substitution: Onward To Carbon-Carbon Bond Forming Reactions!<\/a><\/li>\n<li><a href=\"#two\">Friedel-Crafts Alkylation Of Aromatic Rings<\/a><\/li>\n<li><a href=\"#three\">The Role of The Lewis Acid In Friedel-Crafts Alkylation Is To Activate The Alkyl Halide<\/a><\/li>\n<li><a href=\"#four\">The Key C-C Bond Forming Step\u00a0 Is Attack Of The Aromatic Ring Upon\u00a0 The Carbocation (<em>or carbocation-like<\/em>) Electrophile<\/a><\/li>\n<li><a href=\"#five\">Watch Out! Carbocation Rearrangements Can Occur In The Friedel-Crafts Alkylation Reaction<\/a><\/li>\n<li><a href=\"#six\">If A Hydride Shift Or Alkyl Shift Will Result In A More Stable Carbocation, Assume It Will Happen<\/a><\/li>\n<li><a href=\"#seven\">Limitations of the Friedel-Crafts Alkylation<\/a><\/li>\n<li><a href=\"#eight\">Friedel-Crafts Acylation<\/a><\/li>\n<li><a href=\"#nine\">The Mechanism Of The Friedel-Crafts Acylation Reaction<\/a><\/li>\n<li><a href=\"#ten\">No Rearrangements Occur In The Friedel-Crafts Acylation<\/a><\/li>\n<li><a href=\"#eleven\">Limitations of The Friedel-Crafts Acylation<\/a><\/li>\n<li><a href=\"#twelve\">Summary: Friedel-Crafts Alkylation and Acylation<\/a><\/li>\n<li><a href=\"#notes\"><span class=\"s1\">Notes<\/span><\/a><\/li>\n<li><a href=\"#quiz\">Quiz Yourself!\u00a0<\/a><\/li>\n<li><a href=\"#references\">(Advanced) References and Further Reading<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><strong><a id=\"one\"><\/a>1. Quick Recap On Electrophilic Aromatic Substitution: Onward To\u00a0 Carbon-Carbon Bond Forming Reactions!<\/strong><\/h2>\n<p>This is the third in a series of three posts on the key electrophilic aromatic substitution (EAS) reactions in introductory organic chemistry.<\/p>\n<ul>\n<li>In <a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/04\/18\/electrophilic-aromatic-substitutions-1-halogenation\/\">Part 1<\/a> we covered halogenation (chlorination, bromination, and iodination) of aromatic rings via EAS.<\/li>\n<li>In <a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/04\/30\/electrophilic-aromatic-substitutions-2-nitration-and-sulfonylation\/\">Part 2<\/a> we covered nitration and sulfonylation of aromatic rings via EAS.<\/li>\n<\/ul>\n<p>Taken together, so far we have learned reactions to form carbon-halogen, carbon-nitrogen, and carbon-sulfur bonds.<\/p>\n<p>What important class of bond is missing so far?<\/p>\n<p><em><strong>Carbon-carbon bond forming reactions!<\/strong> [<a href=\"#noteone\">Note 1<\/a>]<\/em><\/p>\n<p>In this post, we&#8217;ll cover two important C\u2013C bond-forming electrophilic aromatic substitution reactions which bear the names of their discoverers, Charles Friedel and James Crafts: <a href=\"http:\/\/gallica.bnf.fr\/ark:\/12148\/bpt6k30410\/f1386.table\">Friedel-Crafts alkylation<\/a> and <a href=\"http:\/\/gallica.bnf.fr\/ark:\/12148\/bpt6k30410\/f1444.table\">Friedel-Crafts acylation<\/a>.<\/p>\n<p>We&#8217;ll also see that these reactions follow the <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/11\/09\/electrophilic-aromatic-substitution-the-mechanism\/\">familiar three-step pattern<\/a> seen in previous electrophilic aromatic substitution reactions, namely:<\/p>\n<ul>\n<li>activation of electrophile with a Lewis acid<\/li>\n<li>attack of the &#8220;activated&#8221; electrophile by the aromatic ring<\/li>\n<li>deprotonation to restore aromaticity<\/li>\n<\/ul>\n<h2><strong><a id=\"two\"><\/a>2. Friedel-Crafts Alkylation Of Aromatic Rings<\/strong><\/h2>\n<p>When an alkyl halide is treated with a Lewis acid in the presence of an aromatic ring,\u00a0 the alkyl group can be added to the ring (forming C-C) with the loss of a C-H bond. This electrophilic aromatic substitution reaction is known as the <strong>Friedel-Crafts alkylation<\/strong> reaction.<\/p>\n<p>Generally, no reaction occurs in the absence of Lewis acid.\u00a0A common choice for the Lewis acid is aluminum chloride, AlCl<sub>3\u00a0<\/sub>, but many others may be used, such as FeCl<sub>3<\/sub> among others.<\/p>\n<p><strong>Alkyl<\/strong> halides (typically chlorides, bromides, and iodides) must be used, as the reaction fails completely for alkenyl and alkynyl halides.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15928\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-generic-example-of-friedel-crafts-alkylation-of-benzene-with-alkyl-halide-giving-new-alkyl-group-with-lewis-acid-no-alkenyl-or-alkynyl.gif\" alt=\"generic example of friedel crafts alkylation of benzene with alkyl halide giving new alkyl group with lewis acid no alkenyl or alkynyl\" width=\"630\" height=\"327\" \/><\/p>\n<p>Here&#8217;s a specific example using ethyl chloride:<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15929\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-friedel-crafts-alkylation-reaction-specific-example-with-ethyl-chloride-and-alcl3-giving-ethylbenzene.gif\" alt=\"friedel crafts alkylation reaction specific example with ethyl chloride and alcl3 giving ethylbenzene\" width=\"600\" height=\"196\" \/><\/p>\n<h2><strong><a id=\"three\"><\/a>3. The Role of The Lewis Acid In Friedel-Crafts Alkylation Is To Activate The Alkyl Halide<\/strong><\/h2>\n<p>If no reaction occurs in the absence of a Lewis acid, then what is the role of the Lewis acid here?<\/p>\n<p>Like we saw in the two previous posts on electrophilic aromatic substitution reactions, Lewis acids &#8220;activate&#8221; the electrophile by coordinating to the leaving group, making it a weaker base, and a better leaving group\u00a0<em>(AlCl<sub>4<\/sub><sup>\u2013<\/sup> is a weaker base than Cl<sup>\u2013<\/sup> ).\u00a0 <\/em>The\u00a0end result is that coordination of the Lewis acid to the electrophile makes the species a\u00a0<strong>better electrophile.\u00a0<\/strong><\/p>\n<p>For example, with isopropyl chloride (below), the first step is coordination of\u00a0 coordination of AlCl<sub>3<\/sub> to the chlorine atom. This weakens the C-Cl bond, with the result that the Cl can depart (as AlCl<sub>4<\/sub><sup>\u2013<\/sup>\u00a0) to give a secondary carbocation (a better electrophile than isopropyl chloride itself).<\/p>\n<ul>\n<li>With secondary and tertiary halides, full dissociation to a carbocation can occur.<\/li>\n<li>In the case of primary (and methyl) alkyl halides, the electrophile is likely not a &#8220;free&#8221; carbocation, but a &#8220;carbocation-like&#8221; species where the C\u2013Cl bond is considerably weakened\/lengthened.<\/li>\n<li>As we mentioned briefly, no reaction occurs with alkenyl or alkynyl halides, largely because the carbocations of these species are so unstable and difficult to generate.<\/li>\n<\/ul>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15930\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-step-1-of-friedel-crafts-alkylation-mechanism-activation-of-electrophile-with-lewis-acid.gif\" alt=\"step 1 of friedel crafts alkylation mechanism activation of electrophile with lewis acid\" width=\"630\" height=\"463\" \/><\/p>\n<p><span style=\"color: #993366;\"><em>Note: that although here we are showing the carbocation electrophile in the Friedel-Crafts as being generated from an alkyl halide and a Lewis acid, there are other ways to generate a carbocation [<a style=\"color: #993366;\" href=\"#notetwo\">such as through protonation of an alkene, see below<\/a>]. We generally define the Friedel-Crafts alkylation as being the reaction of an aromatic ring with a carbocation (or carbocation-like) intermediate. See <a style=\"color: #993366;\" href=\"#notetwo\">Note 2<\/a> for example.\u00a0<\/em><\/span><\/p>\n<h2><strong><a id=\"four\"><\/a>4. The Key C-C Bond Forming Step\u00a0 Is Attack Of The Aromatic Ring Upon\u00a0 The Carbocation (or carbocation-like) Electrophile\u00a0<\/strong><\/h2>\n<p>Once the electrophile has been activated, the next step of the Friedel-Crafts is attack of the activated electrophile by the aromatic ring. This is also the rate-determining step, as it disrupts the aromaticity of the ring (and its ~36 kcal\/mol of resonance energy).<\/p>\n<p>In this step a C\u2013C (pi) bond from the aromatic ring breaks, and a new C\u2013C sigma bond is formed, leading to a carbocation intermediate:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15931\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-step-2-of-friedel-crafts-alkylation-mechanism-attack-of-electrophile-by-aromatic-ring.gif\" alt=\"step 2 of friedel crafts alkylation mechanism attack of electrophile by aromatic ring\" width=\"600\" height=\"205\" \/><\/p>\n<p>The last step is deprotonation of\u00a0 C\u2013H by a weak base (e.g. Cl <sup>&#8211;<\/sup> ) to restore aromaticity at the ring:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15932\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-step-3-of-friedel-crafts-alkylation-mechanism-deprotonation-of-aromatic-ring-giving-benzene.gif\" alt=\"step 3 of friedel crafts alkylation mechanism deprotonation of aromatic ring giving benzene\" width=\"600\" height=\"277\" \/><\/p>\n<p><span style=\"color: #993366;\"><em>[another way to depict the curved arrows in this reaction is to dissociate Cl<sup>&#8211;<\/sup> from AlCl<sub>4<\/sub><sup>&#8211;\u00a0<\/sup>and then employ it as the base. Either way it works out to the same thing].\u00a0<\/em><\/span><\/p>\n<p>Note that AlCl<sub>3<\/sub> is regenerated here, allowing it to be used again in step 1 with another equivalent of the alkyl halide. Hence, AlCl<sub>3<\/sub> can act as a<strong> catalyst<\/strong> in this reaction, since it increases the rate of reaction but is not consumed by it.<\/p>\n<h2><strong><a id=\"five\"><\/a>5. Look Out! Carbocation Rearrangements Can Occur In The Friedel-Crafts Alkylation Reaction<\/strong><\/h2>\n<p>Many university science courses are taught in units, where what you learn in one module has pretty much zero overlap with what you learn in another.<\/p>\n<p>Needless to say,\u00a0<em>organic chemistry is not like this.\u00a0<\/em>You&#8217;ve probably already experienced a situation where concepts you learned in Org 1 reverberate back to Org 2 chapters in unexpected ways. Well, get ready for another fun example.<\/p>\n<p>We showed above how ethyl chloride reacts with benzene and AlCl<sub>3<\/sub> in the Friedel-Crafts alkylation to provide ethylbenzene.<\/p>\n<p>Extension of this reaction from ethyl chloride to propyl chloride should correspondingly give propylbenzene.<\/p>\n<p><em>Right?<\/em><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15933\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-example-of-rearrangement-of-alkyl-halide-in-the-friedel-crafts-alkylation-reaction.gif\" alt=\"example of rearrangement of alkyl halide in the friedel crafts alkylation reaction\" width=\"600\" height=\"288\" \/><\/p>\n<p>What the&#8230;.<em> isopropylbenzene?\u00a0<\/em><\/p>\n<p>How did this happen?<\/p>\n<p>Quick trip down memory lane.\u00a0 Remember this beloved reaction from Org 1?<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15934\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-mechanism-for-1-2-hydride-shift-in-the-friedel-crafts-alkylation-reaction.gif\" alt=\"mechanism for 1 2 hydride shift in the friedel crafts alkylation reaction\" width=\"600\" height=\"170\" \/><\/p>\n<p>Ah, the hydride shift. <strong>Carbocations can rearrange via hydride and alkyl shifts such that a less stable carbocation is transformed into a more stable carbocation.<\/strong><\/p>\n<p>In the Friedel-Crafts, we&#8217;ve seen that coordination of a Lewis acid to an alkyl halide resulted in a carbocation (or in the case of primary alkyl halides, at least a &#8220;carbocation-like&#8221; species) that is then attacked by the aromatic ring in the rate-determining step.<\/p>\n<h2><a id=\"six\"><\/a>6. If A Hydride Shift Or Alkyl Shift Will Result In A More Stable Carbocation, It Will Happen<\/h2>\n<p>So what is happening here is really no different:\u00a0<strong>if a carbocation can rearrange to a more stable carbocation through a hydride or alkyl shift, it will do so.\u00a0<\/strong><\/p>\n<p><em>Organic chemistry 2<\/em>: <em>the course where first-semester concepts come back to bite you in the ass<\/em>.\u2122<\/p>\n<p>Here&#8217;s what happens in the case of propyl chloride.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15935\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/8-friedel-crafts-alkylation-reaction-carbocation-rearrangement.gif\" alt=\"friedel crafts alkylation reaction carbocation rearrangement\" width=\"630\" height=\"435\" \/><\/p>\n<p>A shift of hydride from C<sub>2<\/sub> to C<sub>1<\/sub> results in a secondary carbocation, which is then attacked by the aromatic ring.<\/p>\n<p>Bottom line for the Friedel-Crafts alkylation reaction:<\/p>\n<ul>\n<li>assume the alkyl halide goes through a carbocation<\/li>\n<li>assume that if the carbocation can rearrange to form a more stable carbocation through a hydride (or alkyl) shift,\u00a0 it will.<\/li>\n<\/ul>\n<p>Another example of a rearrangement in the FC alkylation included in the footnotes just for fun. [<a href=\"#notethree\">Note 3<\/a>]<\/p>\n<h2><strong><a id=\"seven\"><\/a>7. Limitations of the Freidel-Crafts Alkylation<\/strong><\/h2>\n<p>Final note on the Friedel-Crafts alkylation: a few drawbacks.<\/p>\n<ul>\n<li>First, as we&#8217;ve seen, <strong>carbocation rearrangements<\/strong> can occur. <span style=\"color: #993366;\"><em>[There are ways of circumventing this issue indirectly, which we&#8217;ll hint at below [<a style=\"color: #993366;\" href=\"#skip\">skip to bottom<\/a>].<\/em><\/span><\/li>\n<li>Second, the Friedel-Crafts alkylation tends not to work well with electron-poor aromatic rings, particularly strongly deactivating substituents such as CF<sub>3<\/sub>, NO<sub>2<\/sub>, SO<sub>3<\/sub>H, and so forth. Halogens are OK.<\/li>\n<li>Third &#8211; and this is more of a practical issue than anything else, so is often ignored &#8211; the product of the FC alkylation is often a better nucleophile than the starting material. (Recall that alkyl groups are activating.)\u00a0 The result can be a bit like the Cookie Monster in a Chips Ahoy! factory &#8211; it can&#8217;t stop at just one, resulting in multiple alkylations.<\/li>\n<\/ul>\n<h2><strong><a id=\"eight\"><\/a>8. Friedel-Crafts Acylation<\/strong><\/h2>\n<p>A process related to the Friedel-Crafts alkylation, called <strong>Friedel-Crafts acylation<\/strong>, was discovered by Friedel and Crafts around the same time (1877). If a Lewis acid is added to an acyl halide in the presence of an aromatic ring, an electrophilic aromatic substitution reaction can occur whereby the acyl group adds to the aromatic ring (with loss of HX).<\/p>\n<p>As with the F.C. alkylation, the specific Lewis acid in the Friedel-Crafts acylation can vary. Aluminum chloride (AlCl<sub>3<\/sub>) is often used, but FeCl<sub>3<\/sub> and other Lewis acids will also do the job.<\/p>\n<p>Here&#8217;s a general example of the Friedel-Crafts acylation:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15936\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/9-friedel-crafts-acylation-reaction-example-generic-lewis-acid-acyl-halide-bonds-formed-and-broken.gif\" alt=\"friedel crafts acylation reaction example generic lewis acid acyl halide bonds formed and broken\" width=\"630\" height=\"287\" \/><\/p>\n<p>A specific example is the reaction between acetyl chloride and benzene catalyzed by aluminum chloride:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15937\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/10-specific-example-of-friedel-crafts-acylation-reaction-benzene-acetyl-chloride-alcl3.gif\" alt=\"specific example of friedel crafts acylation reaction benzene acetyl chloride alcl3\" width=\"600\" height=\"183\" \/><\/p>\n<h2><strong><a id=\"nine\"><\/a>9. The Mechanism Of The Friedel-Crafts Acylation Reaction<\/strong><\/h2>\n<p>So how does the Friedel-Crafts acylation reaction work?<\/p>\n<p>As with FC alkylation, the first step is activation of the electrophile. Lewis acid coordinates to the halogen, and departure of the halogen (as AlCl<sub>4<\/sub><sup>\u2013<\/sup>) results in a fairly stable, resonance-stabilized carbocation know as the &#8220;acylium ion&#8221;.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15938\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/11-mechanism-of-friedel-crafts-acylation-step-1-activation-of-electrophile-with-lewis-acid.gif\" alt=\"mechanism of friedel crafts acylation step 1 activation of electrophile with lewis acid\" width=\"630\" height=\"178\" \/><\/p>\n<p>The acylium ion is the active electrophile in the Friedel-Crafts acylation reaction. Once formed, the acylium ion is attacked by the aromatic ring:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15939\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/12-mechanism-of-friedel-crafts-acylation-step-2-attack-of-activated-electrophile-by-benzene.gif\" alt=\"mechanism of friedel crafts acylation step 2 attack of activated electrophile by benzene\" width=\"600\" height=\"283\" \/><\/p>\n<p>As with the Friedel-Crafts alkylation, the final step is deprotonation at carbon to regenerate the aromatic ring.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15940\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/13-friedel-crafts-acylation-mechanism-step-3-deprotonation-restoring-aromaticity.gif\" alt=\"friedel crafts acylation mechanism step 3 deprotonation restoring aromaticity\" width=\"600\" height=\"220\" \/><\/p>\n<h2><a id=\"ten\"><\/a>10. No Rearrangements Occur In The Friedel-Crafts Acylation<\/h2>\n<p>Unlike the Friedel-Crafts alkylation, no rearrangement occurs with the Friedel-Crafts acylation.<\/p>\n<p>This opens up a &#8220;workaround&#8221; to use the Friedel-Crafts acylation to obtain products that are otherwise difficult to obtain through the Friedel-Crafts alkylation due to carbocation rearrangements. (We&#8217;ll talk about this in detail in a future article, but here we&#8217;ll just give a taste).<\/p>\n<p>For instance, let&#8217;s look at how we could use this to produce propylbenzene, which we saw could not be made from the Friedel-Crafts alkylation reaction of benzene with AlCl<sub>3<\/sub> and 1-propylchloride.<\/p>\n<p>The first step here is to perform a Friedel-Crafts acylation reaction between benzene and propionylchloride, perhaps catalyzed by AlCl<sub>3<\/sub>. This gives us ethyl phenyl ketone.<\/p>\n<p>The next step is to perform a reduction of the ketone to an alkane, which (as we&#8217;ll soon see) can be performed in various ways. This gives us 1-propylbenzene.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15941\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/14-rearrangement-workaround-in-the-friedel-crafts-acylation-giving-an-alkylation-equivalent-wtih-no-rearrangement.gif\" alt=\"rearrangement workaround in the friedel crafts acylation giving an alkylation equivalent wtih no rearrangement\" width=\"630\" height=\"319\" \/><\/p>\n<p><em><span style=\"color: #993366;\">[Commenter Victor, from the<\/span> <a href=\"https:\/\/www.chemistryhelpcenter.org\/\">Chemistry Help Center<\/a>,<span style=\"color: #993366;\"> helpfully notes that there is a fourth way of doing it &#8211; converting the ketone to a thioketal, and then reducing it down to the alkane with Raney nickel.<\/span><\/em><span style=\"color: #993366;\"> ]<\/span><\/p>\n<p><a id=\"skip\"><\/a> We will talk more about synthetic pathways for aromatic molecules in a future post.<\/p>\n<h2><strong><a id=\"eleven\"><\/a>11. Limitations of The Friedel-Crafts Acylation<\/strong><\/h2>\n<ul>\n<li>Similarly to alkylation, Friedel-Crafts acylation tends to fail on aromatic rings with strongly deactivating groups such as nitro, CF<sub>3<\/sub>, sulfonyl and so on. Halogenated aromatics still work, however.<\/li>\n<li><span style=\"color: #993366;\"><em>Put this in the &#8220;probably don&#8217;t need to know category&#8221;, but catalyst turnover in the Friedel-Crafts acylation isn&#8217;t great. In &#8220;real life&#8221;, a stoichiometric amount of AlCl<sub>3<\/sub> is generally required since the AlCl<sub>3<\/sub> coordinates strongly to the ketone product.\u00a0<\/em><\/span><\/li>\n<\/ul>\n<h2><a id=\"twelve\"><\/a>12. Summary: Friedel-Crafts Alkylation and Acylation<\/h2>\n<p>Since they form carbon-carbon bonds, the Friedel-Crafts alkylation and acylation reactions are particularly important electrophilic aromatic substitution reactions.\u00a0 Together with bromination, chlorination, nitration, and sulfonylation they round out the six core electrophilic aromatic substitution reactions.<\/p>\n<p>Before we finish our treatment of electrophilic aromatic substitution, it&#8217;s worth going into detail on one more facet of the Friedel-Crafts that often gives students headaches; the\u00a0<em>intramolecular\u00a0<\/em>versions.<\/p>\n<p><strong>Next Post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2018\/05\/30\/intramolecular-friedel-crafts-reactions\/\">Intramolecular Friedel-Crafts Reactions<\/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\/2018\/05\/30\/intramolecular-friedel-crafts-reactions\/\" class=\"\"><span>Intramolecular Friedel-Crafts Reactions<\/span><\/a><\/li><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\/10\/22\/aromatic-synthesis-2-polarity-reversal\/\" class=\"\"><span>Synthesis of Benzene Derivatives (2) \u2013 Polarity Reversal<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/08\/22\/rearrangement-reactions-2-alkyl-shifts\/\" class=\"\"><span>Carbocation Rearrangement Reactions (2) \u2013 Alkyl Shifts<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/reaction-guide\/friedel-crafts-alkylation-of-arenes\/\" class=\"\"><span>Friedel-Crafts acylation of aromatic groups to give ketones (MOC Membership)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/reaction-guide\/friedel-crafts-alkylation-of-arenes\/\" class=\"\"><span>Friedel Crafts alkylation of arenes (MOC Membership)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/02\/26\/rearrangements-in-alkene-addition-reactions\/\" class=\"\"><span>Rearrangements in Alkene Addition Reactions<\/span><\/a><\/li><\/ul><\/div>\n<p><a id=\"noteone\"><\/a><strong>Note 1<\/strong>. Bonus points if you said &#8220;carbon-oxygen&#8221;\u00a0 as a type of bond we haven&#8217;t seen formed in EAS.\u00a0 Direct electrophilic oxygenation of benzene rings is tricky to do in the lab. For our purposes, forming C-O on an aromatic ring is usually done <em>indirectly<\/em>,\u00a0by means other than a direct EAS. Two ways we&#8217;ll explore in due course are the <a href=\"https:\/\/www.masterorganicchemistry.com\/reaction-guide\/baeyer-villiger-reaction\/\">Baeyer-Villiger oxidation<\/a> and certain <a href=\"https:\/\/www.masterorganicchemistry.com\/reaction-guide\/reactions-of-diazonium-salts\/\">reactions of diazonium salts.\u00a0<\/a><\/p>\n<p><a id=\"notetwo\"><\/a>\u00a0<strong>Note 2. <\/strong>Another way of performing a Friedel-Crafts alkylation is to generate the carbocation through protonation of an alkene. This works best when a fairly stable carbocation is generated, such as the <em>t<\/em>-butyl carbocation generated through protonation of 2-methylpropene.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15942\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F1-addition-of-acid-to-alkenes-gives-carbocation-tert-butyl-group.gif\" alt=\"addition of acid to alkenes gives carbocation tert butyl group\" width=\"600\" height=\"267\" \/><\/p>\n<p><a id=\"notethree\"><\/a><strong>Note 3<\/strong>. Bonus example with alkyl shift.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15943\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F2-rearrangement-in-friedel-crafts-alkylation-with-1-2-shift-of-alkyl-group.gif\" alt=\"rearrangement in friedel crafts alkylation with 1 2 shift of alkyl group\" width=\"630\" height=\"284\" \/><\/p>\n<p><strong><a id=\"notefour\"><\/a>Note 4<\/strong>. Last post we learned that sulfonyl groups can be removed with strong acid, and I alluded to another group that can be removed that would be covered in the next post (i.e. this post).\u00a0 That group is <em>t<\/em>-butyl, which can be removed under forcing conditions, with strong acid. This works because the\u00a0<em>t<\/em>-butyl carbocation is relatively stable and the reverse of the Friedel-Crafts alkylation is therefore feasible.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15944\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F3-strong-acid-in-friedel-crafts-can-remove-tert-butyl-group.gif\" alt=\"strong acid in friedel crafts can remove tert butyl group\" width=\"600\" height=\"431\" \/><\/p>\n<hr \/>\n<h2><strong><a id=\"quiz\"><\/a>Quiz Yourself!\u00a0<\/strong><\/h2>\n<p>&nbsp;<\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0525-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\/0526-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\/0527-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\/0528-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\/0529-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<p>Friedel-Crafts alkylation:<\/p>\n<ol>\n<li>Jie Jack Li describes in his book <em>Name Reactions<\/em>:<br \/>\n\u201cThe discovery of the Friedel\u2013Crafts reaction was the fruit of serendipity and keen observation. In 1877, both Friedel and Crafts were working in Charles A. Wurtz\u2019s laboratory. In order to prepare amyl iodide, they treated amyl chloride with aluminum and iodide using benzene as the solvent. Instead of amyl iodide, they ended up with amylbenzene! Unlike others before them who may have simply discarded the reaction, they thoroughly investigated the Lewis acid-catalyzed alkylations and acylations and published more than 50 papers and patents on the Friedel\u2013Crafts reaction, which has become one of the most useful organic reactions.\u201d<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/link.springer.com\/chapter\/10.1007\/978-3-642-01053-8_101\">10.1007\/978-3-642-01053-8_101<\/a><\/li>\n<li><strong>Sur une nouvelle methode generale de synthese d\u2019hydrocarbures, d\u2019acetones, etc.<br \/>\n<\/strong> Friedel and J. M. Crafts<strong><br \/>\n<\/strong><em>Compt. Rend. <\/em><strong>1877 <\/strong><em>84<\/em>, 1392-1395<br \/>\nThe classic, original paper in French by Friedel and Crafts on the <em>alkylation<\/em> of aromatics (benzene in this case) with alkyl chlorides with AlCl\u00ad<sub>3<\/sub>.<\/li>\n<li><strong>REARRANGEMENTS IN THE FRIEDEL-CRAFTS ALKYLATION OF BENZENE<\/strong><br \/>\nHENRY GILMAN and R. N. MEALS<br \/>\n<em>The Journal of Organic Chemistry<\/em> <strong>1943,<\/strong> <em>08<\/em> (2), 126-146<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo01190a003\">10.1021\/jo01190a003<\/a><br \/>\nThis paper by the legendary American Chemist Prof. Henry Gilman (Iowa State) carefully studies the alkylation of benzene by long-chain alkyl halides (C10 and above). This is a monumental effort, especially considering this was prior to modern chromatographic or spectroscopic techniques (e.g. GC or NMR) that would make analysis of mixtures and characterization of these compounds so much easier.George A. Olah, who received the Nobel Prize in Chemistry in 1994, was well-known for his work in superacid and Friedel-Crafts chemistry. Here are a selection of his papers relevant to Friedel-Crafts alkylation:<\/li>\n<li><strong>Aromatic Substitution. VI. Intermediate Complexes and the Reaction Mechanism of Friedel-Crafts Alkylations and Acylations<br \/>\n<\/strong>G. A. Olah and S. J. Kuhn<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em><strong> 1958, <\/strong><em>80<\/em> (24), 6541-6545<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01557a022\">10.1021\/ja01557a022<\/a><\/li>\n<li><strong>Aromatic Substitution. XVI.1 Friedel-Crafts Isopropylation of Benzene and Methylbenzenes with Isopropyl Bromide and Propylene<br \/>\n<\/strong>George A. Olah, Sylvia H. Flood, Stephen J. Kuhn, Maryanne E. Moffatt, and Nina A. Overchuck<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em><strong> 1964, <\/strong><em>86<\/em> (6), 1046-1054<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ja01060a016\">1021\/ja01060a016<\/a><\/li>\n<li><strong>Aromatic Substitution. XVIII.1 Friedel-Crafts t-Butylation of Benzene and Methylbenzenes with t-Butyl Bromide and Isobutylene<br \/>\n<\/strong>George A. Olah, Sylvia H. Flood, and Maryanne E. Moffatt<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em><strong> 1964, <\/strong><em>86<\/em> (6), 1060-1064<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01060a018?src=recsys\">1021\/ja01060a018<\/a><\/li>\n<li><strong>Aromatic Substitution. XIX.1 Friedel-Crafts Isopropylation and t-Butylation of Halobenzenes<br \/>\n<\/strong>George A. Olah, Sylvia H. Flood, and Maryanne E. Moffatt<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em><strong> 1964, <\/strong><em>86<\/em> (6), 1065-1066<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01060a019\">1021\/ja01060a019<\/a><\/li>\n<li><strong>Aromatic Substitution. XXV.1 Selectivity in the Friedel-Crafts Benzylation, Isopropylation, and <em>t<\/em>-Butylation of Benzene and Toluene<br \/>\n<\/strong>George A. Olah and Nina A. Overchuk<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em><strong> 1965, <\/strong><em>87<\/em> (24), 5786-5788<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00952a047\">1021\/ja00952a047<\/a><br \/>\nThe first sentence in this paper is of note: \u201cFriedel-Crafts alkylations are notorious for their unreliable kinetic behavior\u201d. This is because they are largely heterogeneous, or occur in 2 phases. Also, the footnote indicates that inquiries should be addressed to the Department of Chemistry at the Western Reserve University, Cleveland, OH \u2013 before it merged and became Case Western Reserve University.<\/li>\n<li><strong>Aromatic substitution. XXVIII. Mechanism of electrophilic aromatic substitutions<br \/>\n<\/strong>George A. Olah<strong><br \/>\n<\/strong><em>Acc. Chem. Res.,<\/em><strong> 1971, <\/strong><em>4<\/em> (7), 240-248<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ar50043a002\">10.1021\/ar50043a002<\/a><br \/>\nAn account by Prof. Olah on the work he had carried out studying the mechanism of various types of electrophilic aromatic substitution reactions \u2013 nitration, halogenation, as well as Friedel-Crafts acylation and alkylation.<\/li>\n<li><strong>Aromatic substitution. XXXVII. Stannic and aluminum chloride catalyzed Friedel-Crafts alkylation of naphthalene with alkyl halides. Differentiation of kinetically and thermodynamically controlled product compositions, and the isomerization of alkylnaphthalenes<br \/>\n<\/strong>George A. Olah and Judith A. Olah<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em><strong> 1976, <\/strong><em>98<\/em> (7), 1839-1842<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00423a032\">1021\/ja00423a032<\/a><br \/>\nThis is a similar paper by Prof. Olah and his wife, Judith Olah, on the mechanism of Friedel-Crafts alkylation, except using naphthalene instead of benzene. Naphthalene is different in that there are two sites for monosubstitution \u2013 the a and b positions.<\/li>\n<li><strong>Friedel-Crafts alkylation of anisole and its comparison with toluene. Predominant ortho-para substitution under kinetic conditions and the effect of thermodynamic isomerizations<br \/>\n<\/strong>George A. Olah, Judith A. Olah, and Toshiyuki Ohyama<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em><strong> 1984, <\/strong><em>106<\/em> (18), 5284-5290<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00330a042\">1021\/ja00330a042<\/a><br \/>\nA surprising sentence in this paper: \u201cNo systematic study of the alkylation of anisole was, however, yet reported. Consequently we undertook such a study and report our results\u201d. Sometimes science has these low-hanging fruit, and thoroughly reading the literature can lead you to them.The following papers are related to dealkylation, isomerization, or transfer alkylation under Friedel-Crafts conditions:Friedel-Crafts acylation:<\/li>\n<li><strong>DESOXYBENZOIN<br \/>\n<\/strong> F. H. Allen and W. E. Barker<strong><br \/>\n<\/strong><em>Org. Synth.<\/em><strong> 1932, <\/strong><em>12<\/em><strong>, 16<br \/>\nDOI: <\/strong><a href=\"http:\/\/www.orgsyn.org\/demo.aspx?prep=CV2P0156\">10.15227\/orgsyn.012.0016<\/a><strong><br \/>\n<\/strong>A fairly representative experimental procedure for a Friedel-Crafts acylation in <em>Organic Syntheses<\/em>, a well-known source for reliable, independently tested synthetic organic experimental laboratory procedures. The product desoxybenzoin would be better known today as dihydrochalcone.<\/li>\n<li><strong>Aromatic Substitution. XXII. Acetylation of Benzene, Alkylbenzenes, and Halobenzenes with Methyloxocarbonium (Acetylium) Hexafluoro- and Hexachloroantimonate<br \/>\n<\/strong>George A. Olah, Stephen J. Kuhn, Sylvia H. Flood, and Barbara A. Hardie<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em><strong> 1964, <\/strong><em>86<\/em> (11), 2203-2209<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ja01065a020\">1021\/ja01065a020<\/a><br \/>\nThis paper deals with the acetylation of aromatics with preformed CH<sub>3<\/sub>CO<sup>+<\/sup> salts, which Prof. Olah figured how to isolate using SbF<sub>5<\/sub>. Also, note where these papers were submitted <em>from<\/em> \u2013 Prof. Olah fled from Hungary in the 1950\u2019s to Canada and joined the Dow Chemical Company there.<\/li>\n<li><strong>Aromatic substitution. XXIX. Friedel-Crafts acylation of benzene and toluene with substituted acyl halides. Effect of substituents and positional selectivity<br \/>\n<\/strong>George A. Olah and Shiro Kobayashi<br \/>\n<em>Journal of the American Chemical Society<\/em><strong> 1971, <\/strong><em>93<\/em> (25), 6964-6967<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja00754a045\">1021\/ja00754a045<\/a><br \/>\nThis is a mechanistic study of Friedel-Crafts acylation (or \u2018benzoylation\u2019 in this case) using the Hammett approach, a classic tool in physical organic chemistry. More reactive electrophiles have lower <em>k<sub>t<\/sub>\/k<sub>b<\/sub> <\/em>ratios and low <em>o\/p<\/em> selectivity, while less reactive electrophiles have higher <em>k<sub>t<\/sub>\/k<sub>b<\/sub><\/em> ratios and <em>high<\/em> <em>o\/p<\/em> selectivity. <em>k<sub>t<\/sub>\/k<sub>b<\/sub> <\/em>in this case refers to the relative rate of reacting with toluene vs. benzene.Oxygenation (or oxyfunctionalization) of hydrocarbons and aromatics is definitely possible with the right conditions, as the following two papers describe. Prof. George Olah has written a series of papers on the subject.<\/li>\n<li><strong>Oxyfunctionalization of hydrocarbons. 8. Electrophilic hydroxylation of benzene, alkylbenzenes, and halobenzenes with hydrogen peroxide in superacids<br \/>\n<\/strong>George A. Olah and Ryuichiro Ohnishi<strong><br \/>\n<\/strong><em>The Journal of Organic Chemistry<\/em><strong> 1978, <\/strong><em>43<\/em> (5), 865-867<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo00399a014\">1021\/jo00399a014<\/a><\/li>\n<li><strong>Oxyfunctionalization of hydrocarbons. 14. Electrophilic hydroxylation of aromatics with bis(trimethylsilyl) peroxide\/triflic acid<br \/>\n<\/strong>George A. Olah and Thomas D. Ernst<br \/>\n<em>The Journal of Organic Chemistry<\/em><strong> 1989, <\/strong><em>54<\/em> (5), 1204-1206<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/jo00266a041\">1021\/jo00266a041<\/a><strong><br \/>\n<\/strong>In this paper, bis(trimethylsilyl)peroxide (TMSOOTMS) is used as the oxidant.<\/li>\n<\/ol>\n<p>&#8216;,&#8217;EAS Reactions (3) &#8211; Friedel-Crafts Acylation and Friedel-Crafts Alkylation<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Friedel Crafts Alkylation and Acylation Aromatic rings will form C-C bonds when treated with alkyl or acyl halides in the presence of a strong Lewis <\/p>\n","protected":false},"author":1,"featured_media":15927,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1297],"tags":[321,1334,1333,1335,293],"post_folder":[],"class_list":["post-11599","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-aromatic-reactions","tag-friedel-crafts","tag-friedel-crafts-acylation","tag-friedel-crafts-alkylation","tag-lewis-acid","tag-rearrangements"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>EAS Reactions (3) - Friedel-Crafts Acylation and Friedel-Crafts Alkylation<\/title>\n<meta name=\"description\" content=\"What is Friedel-Crafts acylation and Friedel-Crafts alkylation, and what are their mechanisms? 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