{"id":6017,"date":"2020-10-13T12:33:35","date_gmt":"2020-10-13T07:03:35","guid":{"rendered":"http:\/\/astan.lk\/al_virtualclassroom\/?p=6017"},"modified":"2020-10-13T12:33:21","modified_gmt":"2020-10-13T07:03:21","slug":"benzenes-reactions","status":"publish","type":"post","link":"https:\/\/astan.lk\/al_virtualclassroom\/benzenes-reactions\/","title":{"rendered":"Benzenes&#8217; reactions"},"content":{"rendered":"<h3>Electrophilic substitution reactions of benzene<\/h3>\n<p>There is a loosely bound cloud of electrons on both faces of the planar benzene molecule. As with alkenes, this makes benzene reactive towards electrophiles. The first step in this reaction is for the electrophile (E<sup>+<\/sup>) to form a bond with a carbon atom in the benzene ring.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/b1.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-medium wp-image-10897\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/b1-300x76.png\" alt=\"\" width=\"300\" height=\"76\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<p>The intermediate carbocation so formed is stabilized by the delocalization of the positive charge by conjugation with the two \u03c0 bonds. This can be shown by resonance.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/b2.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-medium wp-image-10896\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/b2-300x72.png\" alt=\"\" width=\"300\" height=\"72\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<p>However, in going from benzene to the carbocation the cyclic delocalization of \u03c0 electrons is broken, and the aromatic stabilization energy is lost. Therefore, the intermediate carbocation prefers to lose a proton and re-established the cyclically delocalized electron cloud, rather than reacts with a nucleophile and give an addition product as in the case of alkenes.<\/p>\n<p>The proton is usually taken up by one of the bases (B:<sup>&#8211;<\/sup>) present in the reaction mixture. Thus, the result is the substitution of a H atom on the benzene ring with E.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/b3.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-medium wp-image-10904\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/b3-300x77.png\" alt=\"\" width=\"300\" height=\"77\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<h4>(i) Nitration<\/h4>\n<p>In the presence of the nitration mixture composed of conc. HNO<sub>3<\/sub> and conc. H<sub>2<\/sub>SO<sub>4<\/sub>, nitrobenzene is formed by the substitution of H by a nitro group.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/n.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-10903\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/n.png\" alt=\"\" width=\"244\" height=\"83\" \/><\/a><\/p>\n<p>The electrophile here is <sup>+<\/sup>NO<sub>2<\/sub> generated in the medium by the dehydration of nitric acid by sulphuric acid.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/nit.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-10902\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/nit-300x42.png\" alt=\"\" width=\"393\" height=\"55\" \/><\/a>The base which takes up the proton in the final step is HSO<sub>4<\/sub><sup>&#8211;<\/sup>.<\/p>\n<p>&nbsp;<\/p>\n<h4>(ii) Friedel \u2013 Crafts alkylation<\/h4>\n<p>During the reaction of benzene with alkyl halides in the presence of a Lewis acid like anhydrous AlCl<sub>3<\/sub>, substitution by an alkyl group takes place.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/fc.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-10901\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/fc.png\" alt=\"\" width=\"249\" height=\"97\" \/><\/a><\/p>\n<p>The electrophile here is R+.<\/p>\n<p>R-Cl + AlCl<sub>3<\/sub> \u00a0\u2192 \u00a0R+AlCl<sub>4<\/sub><sup>&#8211;<\/sup><\/p>\n<p>In cases where R+ is not very stable (eg. +CH3) the species actually reacting with the benzene molecule may be a R-Cl molecule polarized by coordination to AlCl<sub>3<\/sub>, which will transfer R+ to the benzene molecule during the reaction by cleavage of the R-Cl bond.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/fc1.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-10900\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/fc1-300x179.png\" alt=\"\" width=\"340\" height=\"203\" \/><\/a><\/p>\n<p>The base which takes up the proton in the final step is \u00a0AlCl<sub>4<\/sub><sup>&#8211;<\/sup><\/p>\n<p>AlCl<sub>4<\/sub><sup>&#8211;<\/sup> + H<sup>+<\/sup>\u00a0\u2192 AlCl<sub>3<\/sub> + HCl<\/p>\n<p>&nbsp;<\/p>\n<h4>(iii) Friedel \u2013 Crafts acylation<\/h4>\n<p>During the reaction of benzene with acid chlorides in the presence of a Lewis acid like anhydrous AlCl<sub>3<\/sub>, substitution by an acyl group takes place<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/fca.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-10899\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/fca-300x76.png\" alt=\"\" width=\"316\" height=\"80\" \/><\/a><\/p>\n<p>The electrophile here is R-C<sup>+<\/sup>=O.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"\" src=\"http:\/\/www.chemguide.co.uk\/mechanisms\/elsub\/acylalcl3eq.GIF\" width=\"320\" height=\"28\" \/><\/p>\n<p>The base which takes up the proton in the final step is<\/p>\n<p>AlCl<sub>4<\/sub><sup>&#8211;<\/sup> + H<sup>+<\/sup>\u00a0\u2192 AlCl<sub>3<\/sub> + HCl<\/p>\n<p>&nbsp;<\/p>\n<h4>(iv) Halogenation<\/h4>\n<p>When benzene reacts with halogens (Cl<sub>2<\/sub> or Br<sub>2<\/sub>) in the presence of a Lewis acids (such<br \/>\nas FeCl<sub>3<\/sub>, AlCl<sub>3<\/sub>) substitution by a halogen group takes place in the benzene ring.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/bc.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-10909\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/bc.png\" alt=\"\" width=\"200\" height=\"89\" \/><\/a><\/p>\n<p>The efective electrophile here is Cl<sup>+<\/sup>. It is transferred to the benzene ring from the complex AlCl<sub>4<\/sub><sup>&#8211;<\/sup> during the reaction.<\/p>\n<p>AlCl<sub>3<\/sub> + Cl<sub>2<\/sub> \u00a0\u2192 \u00a0 Cl<sub>3<\/sub>Al<sup>&#8211;<\/sup>&#8211;<sup>+<\/sup>Cl-Cl<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/ee.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-10911\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/ee-300x53.png\" alt=\"\" width=\"299\" height=\"53\" \/><\/a><\/p>\n<p>The base which takes up the proton in the final step is \u00a0AlCl<sub>4<\/sub><sup>&#8211;<\/sup> .<\/p>\n<p>AlCl<sub>4<\/sub><sup>&#8211;<\/sup> + H<sup>+<\/sup>\u00a0\u2192 AlCl<sub>3<\/sub> + HCl<\/p>\n<h4><\/h4>\n<h4>Oxidation<\/h4>\n<p>Benzene does not get oxidized by normal oxidizing agents like H<sup>+<\/sup>\/KMnO<sub>4<\/sub>. However, the alkyl group in alkyl substituted benzene can be oxidized by H<sup>+<\/sup>\/KMnO<sub>4<\/sub> to a carboxylic acid group. The benzene ring does not oxidize easily due to its stability. H<sup>+<\/sup>\/K<sub>2<\/sub>Cr<sub>2<\/sub>O<sub>7<\/sub> can also be used for this reaction.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/o.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-medium wp-image-10912\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/o.png\" alt=\"\" width=\"233\" height=\"75\" \/><\/a><\/p>\n<p>Tertiary alkyl groups do not get oxidized under the conditions in which primary and secondary alkyl groups get oxidized. More vigorous conditions under which tertiary alkyl groups can be oxidized also result in cleavage of the benzene ring.<\/p>\n<h4><\/h4>\n<h4>Catalytic hydrogenation<\/h4>\n<p>Although benzene does not undergo electrophilic addition reactions, like alkenes, they can add hydrogen in the presence of suitable catalysts. The temperatures used are higher than for alkenes.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/ch.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-10913\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/ch.png\" alt=\"\" width=\"282\" height=\"80\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Electrophilic substitution reactions of benzene There is a loosely bound cloud of electrons on both faces of the planar benzene molecule. As with alkenes, this makes benzene reactive towards electrophiles. The first step in this reaction is for the electrophile (E+) to form a bond with a carbon atom in the benzene ring. &nbsp; The [&hellip;]<\/p>\n","protected":false},"author":842,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"_monsterinsights_skip_tracking":false,"_monsterinsights_sitenote_active":false,"_monsterinsights_sitenote_note":"","_monsterinsights_sitenote_category":0,"footnotes":""},"categories":[14,1666],"tags":[],"class_list":["post-6017","post","type-post","status-publish","format-standard","hentry","category-chemistry","category-unit-08"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v26.9 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Benzenes&#039; reactions - Learning &amp; Education Portal<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/astan.lk\/al_virtualclassroom\/benzenes-reactions\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Benzenes&#039; reactions - Learning &amp; Education Portal\" \/>\n<meta property=\"og:description\" content=\"Electrophilic substitution reactions of benzene There is a loosely bound cloud of electrons on both faces of the planar benzene molecule. 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