{"id":44,"date":"2008-06-05T06:37:50","date_gmt":"2008-06-05T11:37:50","guid":{"rendered":"http:\/\/organicchemistry.wordpress.com\/?p=44"},"modified":"2008-06-05T06:37:50","modified_gmt":"2008-06-05T11:37:50","slug":"organic-chemistry-help-resonance-and-sn1sn2","status":"publish","type":"post","link":"https:\/\/www.aceorganicchem.com\/blog\/organic-chemistry-help-resonance-and-sn1sn2\/","title":{"rendered":"Organic Chemistry Help: Resonance and SN1\/SN2"},"content":{"rendered":"<p>Hi everybody, I wanted to talk briefly today about resonance and sterics and how it can affect and SN1 or SN2.\u00a0 For background, I hope everyone knows when it comes to SN1 reactions, tertiary substrates are the fastest and primary substrates are the slowest (because of carbocation stability).\u00a0 Conversely, when it comes to SN2, it is all about steric hindrance, so primary is the fastest and\u00a0tertiary is the slowest.\u00a0 But what happens when there are other factors involved?<\/p>\n<p style=\"text-align:center;\"><img loading=\"lazy\" decoding=\"async\" style=\"vertical-align:middle;\" src=\"http:\/\/www.aceorganicchem.com\/i\/blog080605.jpg\" alt=\"\" width=\"430\" height=\"351\" \/><\/p>\n<p>As shown here, the benzyl cation was a\u00a0primary cation, but can undergo resonance stabilization that moves the cation all throughout the ring.\u00a0 This serves to further stabilize it and makes the benzyl cation\u00a0have the reactivity of\u00a0a secondary carbocation when it comes to SN1.<\/p>\n<p>Lesser known is\u00a0the neopentyl bromide, which\u00a0is a primary substrate so it should react quickly via SN2, but it does not.\u00a0 This is because, even though it is primary, it has a very large t-butyl group close, which blocks the reaction site.\u00a0 This makes neopentyl bromide less reactive than one would expect.\u00a0 In fact, it has reactivity somewhere between a secondary and tertiary substrate, for SN2 reactions.<\/p>\n<p>For more information on this, please visit <a title=\"Organic Chemistry\" href=\"http:\/\/www.aceorganicchem.com\" target=\"_blank\">Organic Chemistry<\/a>.<\/p>\n<p>\u00a0<\/p>\n<p>As always, good luck and happy reacting.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Hi everybody, I wanted to talk briefly today about resonance and sterics and how it can affect and SN1 or SN2.\u00a0 For background, I hope everyone knows when it comes to SN1 reactions, tertiary substrates are the fastest and primary substrates are the slowest (because of carbocation stability).\u00a0 Conversely, when it comes to SN2, it [&hellip;]<\/p>\n","protected":false},"author":2,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"om_disable_all_campaigns":false,"_monsterinsights_skip_tracking":false,"_monsterinsights_sitenote_active":false,"_monsterinsights_sitenote_note":"","_monsterinsights_sitenote_category":0,"site-sidebar-layout":"default","site-content-layout":"","ast-site-content-layout":"default","site-content-style":"default","site-sidebar-style":"default","ast-global-header-display":"","ast-banner-title-visibility":"","ast-main-header-display":"","ast-hfb-above-header-display":"","ast-hfb-below-header-display":"","ast-hfb-mobile-header-display":"","site-post-title":"","ast-breadcrumbs-content":"","ast-featured-img":"","footer-sml-layout":"","ast-disable-related-posts":"","theme-transparent-header-meta":"","adv-header-id-meta":"","stick-header-meta":"","header-above-stick-meta":"","header-main-stick-meta":"","header-below-stick-meta":"","astra-migrate-meta-layouts":"default","ast-page-background-enabled":"default","ast-page-background-meta":{"desktop":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center 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