{"id":6014,"date":"2020-10-13T12:41:38","date_gmt":"2020-10-13T07:11:38","guid":{"rendered":"http:\/\/astan.lk\/al_virtualclassroom\/?p=6014"},"modified":"2020-10-13T12:41:28","modified_gmt":"2020-10-13T07:11:28","slug":"nucleophilic-substitution-reaction","status":"publish","type":"post","link":"https:\/\/astan.lk\/al_virtualclassroom\/nucleophilic-substitution-reaction\/","title":{"rendered":"Nucleophilic substitution reaction of Alkyl halides"},"content":{"rendered":"<p>\u2022 To explain the nucleophilic substitution reaction of alkyl halides, the time interval between bond breaking and bond making steps can be considered.<\/p>\n<p>\u2022 When the breaking of the C-X bond and the formation of the new bond to the nucleophile takes place simultaneously, the nucleophilic substitution reaction of the alkyl halide takes place as a one step reaction.<\/p>\n<p>Accordingly, the one step reaction can be presented as follows:<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/al1.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-10670\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/al1-300x93.png\" alt=\"\" width=\"258\" height=\"80\" \/><\/a><\/p>\n<p>\u2022 \u00a0When the formation of the new bond to the nucleophile takes place after the breaking of the C-X bond the nucleophlic substitution reaction of the alkyl halide takes place as a two step reaction.<\/p>\n<p>Accordingly, the reaction that takes place by two steps can be presented as follows.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/al2.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-10669\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/al2-300x194.png\" alt=\"\" width=\"286\" height=\"185\" \/><\/a><\/p>\n<p>The reaction that takes place by two steps goes through an intermediate carbocation. On considering the stability of the carbocation formed, the tertiary alkyl halides (R<sup>1<\/sup>, R<sup>2<\/sup>, R<sup>3<\/sup> = alkyl) which are able to form a more stable tertiary carbocations undergo nucleophilic substitution in two steps. The primary alkyl halides (R<sup>1<\/sup>, R<sup>2<\/sup> = H, R<sup>3<\/sup> = H or alkyl) undergo nucleophilic substitution reactions in one step as they are unable to form a stable intermediate carbocation.<\/p>\n<p>The pathway taken by the secondary alkyl halides (R<sup>1<\/sup> = H, R<sup>2<\/sup>, R<sup>3<\/sup> = alkyl) depend on the reaction conditions.<\/p>\n<p>Vinyl and phenyl carbocations are unstable and therefore, they do not react by the two step pathway. They also do not react by the one step path because the C-X bond is stronger than in alkyl halides due to its double bond character. This can be shown by resonance.<\/p>\n<p><a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/al3.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-10668\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/al3.png\" alt=\"\" width=\"212\" height=\"81\" \/><\/a> <a href=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/al4.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-medium wp-image-10667\" src=\"http:\/\/astan.lk\/al_virtualclassroom\/wp-content\/uploads\/2017\/01\/al4-300x61.png\" alt=\"\" width=\"300\" height=\"61\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<p>&nbsp;<\/p>\n<h3><\/h3>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>\u2022 To explain the nucleophilic substitution reaction of alkyl halides, the time interval between bond breaking and bond making steps can be considered. \u2022 When the breaking of the C-X bond and the formation of the new bond to the nucleophile takes place simultaneously, the nucleophilic substitution reaction of the alkyl halide takes place as [&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":[14,1668],"tags":[],"class_list":["post-6014","post","type-post","status-publish","format-standard","hentry","category-chemistry","category-unit-09"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v26.9 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Nucleophilic substitution reaction of Alkyl halides - Learning &amp; 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