{"id":183915,"date":"2025-01-17T08:50:00","date_gmt":"2025-01-17T08:50:00","guid":{"rendered":"https:\/\/learnexams.com\/blog\/?p=183915"},"modified":"2025-01-17T08:50:04","modified_gmt":"2025-01-17T08:50:04","slug":"sodium-borodeuteride-nabd4-and-lithium-aluminum-deuteride-liald4-are-convenient-reagents-for-introducing-deuterium","status":"publish","type":"post","link":"https:\/\/www.learnexams.com\/blog\/2025\/01\/17\/sodium-borodeuteride-nabd4-and-lithium-aluminum-deuteride-liald4-are-convenient-reagents-for-introducing-deuterium\/","title":{"rendered":"Sodium borodeuteride (NaBD4) and lithium aluminum deuteride (LiAlD4) are convenient reagents for introducing deuterium"},"content":{"rendered":"\n<p>Sodium borodeuteride (NaBD4) and lithium aluminum deuteride (LiAlD4) are convenient reagents for introducing deuterium, the mass 2 isotope of hydrogen, into organic compounds. Write the structure of the organic product of the following reactions, clearly showing the position of all the deuterium atoms in each:<\/p>\n\n\n\n<p><mark style=\"background-color:rgba(0, 0, 0, 0)\" class=\"has-inline-color has-ast-global-color-6-color\"><strong>The Correct Answer and Explanation is :<\/strong><\/mark><\/p>\n\n\n\n<p>To determine the structure of the organic products formed in reactions with sodium borodeuteride (NaBD\u2084) and lithium aluminum deuteride (LiAlD\u2084), let\u2019s analyze their behavior as reducing agents and how they incorporate deuterium into organic compounds.<\/p>\n\n\n\n<h3 class=\"wp-block-heading\">Reaction 1: Reduction with NaBD\u2084<\/h3>\n\n\n\n<p>Sodium borodeuteride is primarily used to reduce aldehydes and ketones to alcohols. When it reacts with a carbonyl compound, a deuteride ion (D\u207b) is delivered to the carbonyl carbon.<\/p>\n\n\n\n<h4 class=\"wp-block-heading\">Example Reaction:<\/h4>\n\n\n\n<p>Reduction of acetone (CH\u2083COCH\u2083) with NaBD\u2084:<\/p>\n\n\n\n<ol class=\"wp-block-list\">\n<li>The deuteride ion (D\u207b) from NaBD\u2084 attacks the carbonyl carbon of acetone.<\/li>\n\n\n\n<li>A tetrahedral alkoxide intermediate forms.<\/li>\n\n\n\n<li>Protonation with a source of D\u207a (e.g., D\u2082O) completes the reaction.<\/li>\n<\/ol>\n\n\n\n<p><strong>Product: CD\u2083CHOHCD\u2083<\/strong><\/p>\n\n\n\n<p>Here, all the hydrogen atoms originally in the product alcohol at the \u03b1-position are replaced by deuterium due to the use of NaBD\u2084 and D\u2082O.<\/p>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\">Reaction 2: Reduction with LiAlD\u2084<\/h3>\n\n\n\n<p>Lithium aluminum deuteride is a stronger reducing agent than NaBD\u2084 and can reduce aldehydes, ketones, carboxylic acids, and esters. It also delivers deuteride (D\u207b) during reduction.<\/p>\n\n\n\n<h4 class=\"wp-block-heading\">Example Reaction:<\/h4>\n\n\n\n<p>Reduction of ethyl acetate (CH\u2083COOCH\u2082CH\u2083) with LiAlD\u2084:<\/p>\n\n\n\n<ol class=\"wp-block-list\">\n<li>The ester bond is cleaved, and two equivalents of D\u207b are delivered\u2014one to the carbonyl carbon and one to the alkoxy oxygen.<\/li>\n\n\n\n<li>This generates ethanol-d\u2086 (CD\u2083CD\u2082OD) and a deuterated primary alcohol (CD\u2083CHDOD).<\/li>\n<\/ol>\n\n\n\n<p><strong>Product: CD\u2083CHDOD and CD\u2083CD\u2082OD<\/strong><\/p>\n\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n\n\n\n<h3 class=\"wp-block-heading\">Explanation<\/h3>\n\n\n\n<ul class=\"wp-block-list\">\n<li>Both reagents replace hydrogen with deuterium during reduction by delivering D\u207b to the electrophilic carbonyl carbon.<\/li>\n\n\n\n<li>NaBD\u2084 is selective for aldehydes and ketones, whereas LiAlD\u2084 reduces a broader range of functional groups, including esters.<\/li>\n\n\n\n<li>The position of the deuterium atoms corresponds to where the reducing agent delivers D\u207b and the deuterated solvent supplies D\u207a during protonation.<\/li>\n<\/ul>\n\n\n\n<p>These reactions are valuable for isotopic labeling in research and mechanistic studies.<\/p>\n\n\n\n<p><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Sodium borodeuteride (NaBD4) and lithium aluminum deuteride (LiAlD4) are convenient reagents for introducing deuterium, the mass 2 isotope of hydrogen, into organic compounds. Write the structure of the organic product of the following reactions, clearly showing the position of all the deuterium atoms in each: The Correct Answer and Explanation is : To determine the [&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-183915","post","type-post","status-publish","format-standard","hentry","category-exams-certification"],"_links":{"self":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts\/183915","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=183915"}],"version-history":[{"count":0,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts\/183915\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/media?parent=183915"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/categories?post=183915"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/tags?post=183915"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}