{"id":240590,"date":"2025-07-03T10:37:05","date_gmt":"2025-07-03T10:37:05","guid":{"rendered":"https:\/\/learnexams.com\/blog\/?p=240590"},"modified":"2025-07-03T10:37:07","modified_gmt":"2025-07-03T10:37:07","slug":"attack-of-a-grignard-reagent-such-as-methylmagnesium-bromide-ch3co2ch2ch3","status":"publish","type":"post","link":"https:\/\/www.learnexams.com\/blog\/2025\/07\/03\/attack-of-a-grignard-reagent-such-as-methylmagnesium-bromide-ch3co2ch2ch3\/","title":{"rendered":"Attack of a Grignard reagent such as methylmagnesium bromide (CH3CO2CH2CH3)"},"content":{"rendered":"\n

Attack of a Grignard reagent such as methylmagnesium bromide (CH3CO2CH2CH3) generates on ethyl acetate: CH3MgBr 2) H2O tertiary alcohol primary alcohol secondary alcohol ketone<\/p>\n\n\n\n

\"\"<\/figure>\n\n\n\n

The Correct Answer and Explanation is:<\/mark><\/strong><\/p>\n\n\n\n

The correct answer is tertiary alcohol<\/strong>.<\/p>\n\n\n\n

Explanation:<\/strong><\/p>\n\n\n\n

The reaction shown is the addition of a Grignard reagent, methylmagnesium bromide (CH\u2083MgBr), to an ester, ethyl acetate (CH\u2083COOCH\u2082CH\u2083). This reaction proceeds in two main stages, ultimately resulting in the formation of a tertiary alcohol.<\/p>\n\n\n\n

    \n
  1. First Nucleophilic Attack and Ketone Formation:<\/strong>\u00a0The methyl group (CH\u2083) in the Grignard reagent acts as a potent nucleophile. It attacks the electrophilic carbonyl carbon of the ethyl acetate. This initial attack breaks the carbon-oxygen double bond and forms a tetrahedral intermediate. This intermediate is unstable and quickly collapses. The ethoxy group (\u207bOCH\u2082CH\u2083) is a good leaving group, so it is expelled, and the carbon-oxygen double bond reforms. The product of this first step is a ketone, in this case, acetone (CH\u2083COCH\u2083).<\/li>\n\n\n\n
  2. Second Nucleophilic Attack and Alcohol Formation:<\/strong>\u00a0The reaction does not stop at the ketone. Ketones are also highly reactive towards Grignard reagents. A second molecule of methylmagnesium bromide attacks the carbonyl carbon of the newly formed acetone. This second nucleophilic attack forms a new tetrahedral intermediate, which is a magnesium alkoxide salt.<\/li>\n\n\n\n
  3. Protonation (Aqueous Workup):<\/strong>\u00a0The final step is the addition of water (H\u2082O). The negatively charged oxygen of the alkoxide salt is a strong base and is protonated by water. This step neutralizes the intermediate and generates the final alcohol product. In this specific reaction, the product is 2-methyl-2-propanol, also known as tert-butyl alcohol.<\/li>\n<\/ol>\n\n\n\n

    The carbon atom bonded to the hydroxyl (-OH) group in tert-butyl alcohol is also bonded to three other carbon atoms (three methyl groups). By definition, an alcohol in which the hydroxyl-bearing carbon is attached to three other carbons is a tertiary alcohol<\/p>\n\n\n\n

    \"\"<\/figure>\n","protected":false},"excerpt":{"rendered":"

    Attack of a Grignard reagent such as methylmagnesium bromide (CH3CO2CH2CH3) generates on ethyl acetate: CH3MgBr 2) H2O tertiary alcohol primary alcohol secondary alcohol ketone The Correct Answer and Explanation is: The correct answer is tertiary alcohol. Explanation: The reaction shown is the addition of a Grignard reagent, methylmagnesium bromide (CH\u2083MgBr), to an ester, ethyl acetate (CH\u2083COOCH\u2082CH\u2083). […]<\/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-240590","post","type-post","status-publish","format-standard","hentry","category-exams-certification"],"_links":{"self":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts\/240590","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=240590"}],"version-history":[{"count":0,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/posts\/240590\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/media?parent=240590"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/categories?post=240590"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.learnexams.com\/blog\/wp-json\/wp\/v2\/tags?post=240590"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}