{"id":229409,"date":"2025-06-08T07:03:23","date_gmt":"2025-06-08T07:03:23","guid":{"rendered":"https:\/\/learnexams.com\/blog\/?p=229409"},"modified":"2025-06-08T07:03:25","modified_gmt":"2025-06-08T07:03:25","slug":"draw-the-major-product-of-this-reaction-2","status":"publish","type":"post","link":"https:\/\/www.learnexams.com\/blog\/2025\/06\/08\/draw-the-major-product-of-this-reaction-2\/","title":{"rendered":"Draw the major product of this reaction."},"content":{"rendered":"\n<p>Draw the major product of this reaction. Ignore inorganic byproducts. Assume that the water side product is continuously removed to drive the reaction toward products. TSOH, CH<br>CH<br>OH (2 equiv)<\/p>\n\n\n\n<figure class=\"wp-block-image size-full\"><img decoding=\"async\" src=\"https:\/\/learnexams.com\/blog\/wp-content\/uploads\/2025\/06\/image-278.png\" alt=\"\" class=\"wp-image-229410\"\/><\/figure>\n\n\n\n<p><strong><mark style=\"background-color:rgba(0, 0, 0, 0)\" class=\"has-inline-color has-ast-global-color-1-color\">The Correct Answer and Explanation is:<\/mark><\/strong><\/p>\n\n\n\n<p>The starting compound shown is a <strong>1,3,5-triketone with an ethyl ester on one end<\/strong>. The reaction conditions include:<\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li><strong>TsOH (p-toluenesulfonic acid)<\/strong>: a strong organic acid catalyst.<\/li>\n\n\n\n<li><strong>CH\u2083CH\u2082OH (ethanol), 2 equivalents<\/strong>.<\/li>\n\n\n\n<li>Removal of <strong>water<\/strong>, driving the equilibrium toward the product.<\/li>\n<\/ul>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>Reaction Overview:<\/strong><\/h3>\n\n\n\n<p>This is a <strong>double acetal (or ketal)<\/strong> formation reaction. Acid-catalyzed ketone reaction with alcohols (especially in excess) forms <strong>acetals or ketals<\/strong>. In this molecule, there are two ketone groups and one ester group. Esters are less reactive under these conditions compared to ketones, so the <strong>two ketone groups<\/strong> are the reactive centers.<\/p>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>Mechanism and Product Formation:<\/strong><\/h3>\n\n\n\n<ol class=\"wp-block-list\">\n<li><strong>Ethanol (2 equiv)<\/strong> reacts with each ketone group.<\/li>\n\n\n\n<li>In the presence of <strong>acid catalyst (TsOH)<\/strong>, each ketone undergoes <strong>nucleophilic attack by ethanol<\/strong>, followed by proton transfers and loss of water.<\/li>\n\n\n\n<li>Since water is removed, the equilibrium favors acetal formation.<\/li>\n\n\n\n<li>Each ketone is converted into a <strong>diethexy acetal<\/strong>:\n<ul class=\"wp-block-list\">\n<li>\u2013C=O \u2192 \u2013C(OC\u2082H\u2085)\u2082<\/li>\n<\/ul>\n<\/li>\n<\/ol>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>Final Product:<\/strong><\/h3>\n\n\n\n<p>The major product is a molecule where the <strong>two ketone groups<\/strong> have each been converted to <strong>acetals<\/strong> (diethexy). The ester functional group remains unchanged.<\/p>\n\n\n\n<p><strong>Structural Summary of the Major Product:<\/strong><\/p>\n\n\n\n<ul class=\"wp-block-list\">\n<li>A 7-carbon chain with:\n<ul class=\"wp-block-list\">\n<li>C2: acetal (C bonded to two ethoxy groups)<\/li>\n\n\n\n<li>C4: ester group (unchanged)<\/li>\n\n\n\n<li>C6: acetal (C bonded to two ethoxy groups)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\"><strong>Conclusion (Summary):<\/strong><\/h3>\n\n\n\n<p>This is an <strong>acid-catalyzed acetal formation<\/strong> reaction. The major product is formed by reaction of the two ketones with 2 equivalents of ethanol, forming two acetal groups. The removal of water ensures the equilibrium favors product formation. The ester group does not react under these conditions.<\/p>\n\n\n\n<figure class=\"wp-block-image size-full\"><img decoding=\"async\" src=\"https:\/\/learnexams.com\/blog\/wp-content\/uploads\/2025\/06\/learnexams-banner10-25.jpeg\" alt=\"\" class=\"wp-image-229411\"\/><\/figure>\n","protected":false},"excerpt":{"rendered":"<p>Draw the major product of this reaction. Ignore inorganic byproducts. Assume that the water side product is continuously removed to drive the reaction toward products. TSOH, CHCHOH (2 equiv) The Correct Answer and Explanation is: The starting compound shown is a 1,3,5-triketone with an ethyl ester on one end. The reaction conditions include: Reaction Overview: [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"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 center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"tablet":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"mobile":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""}},"ast-content-background-meta":{"desktop":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"tablet":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""},"mobile":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-opacity":"","overlay-gradient":""}},"footnotes":""},"categories":[25],"tags":[],"class_list":["post-229409","post","type-post","status-publish","format-standard","hentry","category-exams-certification"],"_links":{"self":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts\/229409","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/comments?post=229409"}],"version-history":[{"count":0,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts\/229409\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/media?parent=229409"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/categories?post=229409"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/tags?post=229409"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}