{"id":9320,"date":"2015-12-10T08:00:39","date_gmt":"2015-12-10T13:00:39","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=9320"},"modified":"2026-04-22T12:24:46","modified_gmt":"2026-04-22T17:24:46","slug":"reactions-of-grignard-reagents","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2015\/12\/10\/reactions-of-grignard-reagents\/","title":{"rendered":"Reactions of Grignard Reagents"},"content":{"rendered":"<p><strong>All About The Reactions of Grignard Reagents<\/strong><\/p>\n<ul>\n<li>Grignard reagents are excellent carbon-based nucleophiles as well as strong bases.<\/li>\n<li>They will add to aldehydes and ketones to form alcohols (after a protonation step)<\/li>\n<li>They will add\u00a0<strong>twice\u00a0<\/strong>to esters to give tertiary alcohols.<\/li>\n<li>They will add to the less-substituted side of epoxides<\/li>\n<li>Grignard reagents will also react with carbon dioxide (CO<sub>2<\/sub>) to give carboxylic acids (after acid workup).<\/li>\n<li>Grignard reagents will <strong>not<\/strong> perform S<sub>N<\/sub>2 reactions with alkyl halides. They are also not compatible with carboxylic acids or alcohols.<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-38803\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2025\/02\/00-key-reactions-of-grignard-reagents-summary-addition-to-aldehydes-ketones-esters-epoxides-co2.gif\" alt=\"key reactions of grignard reagents summary addition to aldehydes ketones esters epoxides co2\" width=\"600\" height=\"634\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">Reminder: Grignard Reagents Are Nucleophiles<\/a><\/li>\n<li><a href=\"#two\">Addition of Grignard Reagents To Epoxides<\/a><\/li>\n<li><a href=\"#three\">Reaction of Grignard Reagents With Aldehydes And Ketones<\/a><\/li>\n<li><a href=\"#four\">Reaction of Grignard Reagents With Esters<\/a><\/li>\n<li><a href=\"#five\">Why Do Grignards Add Twice To Esters? The Mechanism<\/a><\/li>\n<li><a href=\"#six\">Summary: Reactions of Grignard Reagents<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quizzes\">Quiz Yourself!<\/a><\/li>\n<li><a href=\"#references\">(Advanced) References and Further Reading<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><strong><a id=\"one\"><\/a>1. Reminder: Grignard Reagents Are Nucleophiles<\/strong><\/h2>\n<p>So far in this series we&#8217;ve introduced <a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/10\/28\/whats-an-organometallic\/\">organometallic compounds<\/a> and said that their carbons tend to be nucleophilic. We&#8217;ve learned <a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/11\/09\/synthesis-of-grignard-and-organolithium-reagents\/\">how to make them<\/a> from alkyl, alkenyl or aryl halides (along with some ways <strong>not<\/strong> to make them!) and saw that they are <a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/11\/13\/organometallics-are-strong-bases\/\">very strong bases<\/a>.<\/p>\n<p>Most interesting about Grignards is that they are carbon-based nucleophiles and we can thus combine Grignard reagents with various electrophilic carbon species to form new carbon-carbon bonds.<\/p>\n<p>And since carbon-carbon bonds constitute the &#8220;backbone&#8221; of molecules in organic chemistry, it turns out that this class of reactions is very useful. As a matter of fact, it won its discoverer, <a href=\"https:\/\/en.wikipedia.org\/wiki\/Victor_Grignard\">Victor Grignard<\/a>, the Nobel Prize for Chemistry back in 1912.<\/p>\n<p>For our purposes, the key carbon-based electrophiles that Grignard reagents react with are <strong>epoxides, aldehydes, ketones, and esters.<\/strong> Let&#8217;s go through them in turn.<\/p>\n<h2><strong><a id=\"two\"><\/a>2. Addition of Grignard Reagents To Epoxides<\/strong><\/h2>\n<p>Epoxides (&#8220;oxiranes&#8221; if you are an IUPAC stickler) are 3-membered cyclic ethers which possess considerable ring strain. \u00a0<a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/01\/26\/epoxides-the-outlier-of-the-ether-family\/\">As we&#8217;ve seen, this ring strain makes them somewhat &#8220;spring loaded&#8221; toward attack by nucleophiles<\/a>, which will result in formation of a new bond to carbon and opening of the ring.<\/p>\n<p>Negatively charged nucleophiles (such as Grignards) tend to react with epoxides in a manner <a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/02\/10\/opening-of-epoxide-with-base\/\">similar to the S<sub>N<\/sub>2 reaction<\/a>: attack occurs at the\u00a0<strong>least substituted\u00a0<\/strong>carbon of the epoxide. Here&#8217;s an example:<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15333\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-addition-of-grignard-reagents-to-epoxides-1.gif\" alt=\"addition of grignard reagents to epoxides\" width=\"600\" height=\"183\" \/><\/p>\n<p>Note the bonds that formed and broke here: we\u00a0<strong>formed<\/strong> a new C-C bond (between carbons A and B), and\u00a0<strong>broke\u00a0<\/strong>a C-O bond (between carbon A and the oxygen). This resulted in a negatively charged oxygen (alkoxide): to produce final alcohol product, we typically quench the reaction with a source of acid, forming O\u2013H.<\/p>\n<p>Here&#8217;s how the reaction works. The hard thing is to recognize that the nucleophile is the pair of electrons in the C-Mg bond: remember from previous posts that carbon is strongly\u00a0\u03b4- (nucleophilic) because of its greater electronegativity as compared to magnesium.<\/p>\n<p>It might be helpful to imagine the Grignard reagent below as CH<sub>3<\/sub>CH<sub>2<\/sub><sup>\u2013\u00a0<\/sup>. Other than that the reaction is fairly straightforward if you&#8217;ve seen an S<sub>N<\/sub>2 reaction before: we simultaneously form C-C and break C-O.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15334\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/2-mechanism-for-the-reaction-of-grignard-reagents-with-epoxides-attack-at-least-substituted-carbon-1.gif\" alt=\"mechanism for the reaction of grignard reagents with epoxides attack at least substituted carbon\" width=\"600\" height=\"333\" \/><\/p>\n<p>Note that this reaction also forms an &#8220;alkoxide&#8221;. In order to obtain our neutral alcohol product at the end, we must perform second step: \u00a0a &#8220;workup&#8221; (&#8220;quench&#8221;) with a source of acid. This is written a variety of ways &#8211; H+, H<sub>3<\/sub>O+, H<sub>2<\/sub>O, or just &#8220;acid workup&#8221;. This step occurs\u00a0<strong>after<\/strong> our key Grignard reaction, for what should be obvious reasons &#8211; being strong bases, Grignard reagents are destroyed by acid.<\/p>\n<p>Another thing to keep in mind is <strong>stereochemistry of the epoxide<\/strong>.Consistent with an S<sub>N<\/sub>2 reaction, if the reaction occurs at a secondary carbon, we will observe\u00a0<strong>inversion of configuration:\u00a0<\/strong><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15335\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-the-attack-of-grignards-at-epoxides-on-the-least-substituted-carbon-is-essentially-an-sn2-reaction-1.gif\" alt=\"the attack of grignards at epoxides on the least substituted carbon is essentially an sn2 reaction\" width=\"600\" height=\"263\" \/><\/p>\n<h2><strong><a id=\"three\"><\/a>3. Reaction of Grignards With Aldehydes and Ketones<\/strong><\/h2>\n<p>A second class of important electrophiles that react with Grignards (and arguably THE most important class of electrophiles) is<strong> aldehydes and ketones.<\/strong> If you haven&#8217;t covered the reactions of these functional groups yet, a short summary would be this: <b>the carbonyl carbon is an electrophile<\/b>, and when nucleophiles react at this carbon, it&#8217;s accompanied by cleavage of the C-O pi bond (\u03c0 bond). (<em>For more on the addition mechanism to carbonyls, see post:<a href=\"https:\/\/www.masterorganicchemistry.com\/2022\/09\/09\/nucleophilic-addition\/\"> Nucleophilic Addition<\/a><\/em>)<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15336\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-addition-of-grignards-to-aldehydes-and-ketones-1.gif\" alt=\"addition of grignards to aldehydes and ketones\" width=\"600\" height=\"264\" \/><\/p>\n<p>Here are some examples of reactions of Grignards with aldehydes and ketones. Note that in each case we are forming a new bond between the carbonyl carbon (labelled A) and the carbon bound to magnesium (labelled B), and we are breaking the C-O pi bond in the process.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15337\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-examples-of-grignard-reagents-reacting-with-aldeydes-and-ketones-to-give-secondary-and-tertiary-alcohols-1.gif\" alt=\"examples of grignard reagents reacting with aldeydes and ketones to give secondary and tertiary alcohols\" width=\"600\" height=\"341\" \/><\/p>\n<p>So how does this reaction work?<\/p>\n<p>Let&#8217;s get familiar with a VERY important mechanism called &#8220;<a href=\"https:\/\/www.masterorganicchemistry.com\/2022\/09\/09\/nucleophilic-addition\/\">addition<\/a>&#8221; (sometimes called, &#8220;1,2-addition&#8221;). <strong>This is by far the most important reaction of the carbonyl group<\/strong>, and if you give yourself a chicken for every time you will see variations of it in Org 2, you will have a lot of eggs in your room by the end of the semester.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15338\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-the-mechanism-for-simple-reaction-of-grignard-reagents-with-aldehydes-and-ketones-1.gif\" alt=\"the mechanism for simple reaction of grignard reagents with aldehydes and ketones\" width=\"600\" height=\"321\" \/><\/p>\n<p>Note that this reaction also forms an &#8220;alkoxide&#8221;. In order to obtain our neutral alcohol product at the end, we must perform a &#8220;workup&#8221; (&#8220;quench&#8221;) with a source of acid, forming O-H.<\/p>\n<h2><strong><a id=\"four\"><\/a>4. Reaction of Grignard Reagents With Esters<\/strong><\/h2>\n<p>Esters are close relatives of aldehydes and ketones: they consist of a carbonyl group directly attached to an OR group. As you might expect, they react with Grignards in a similar fashion to aldehydes and ketones: with formation of a new C-C bond and breakage of a C-O (pi bond).<\/p>\n<p>However, there&#8217;s a twist with the reaction of esters that isn&#8217;t present with aldehydes and ketones. Look carefully: what&#8217;s different?<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15339\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-addition-of-grignards-and-organolithium-to-esters-addition-twice-not-once-1.gif\" alt=\"addition-of-grignards-and-organolithium-to-esters-addition-twice-not-once\" width=\"600\" height=\"301\" \/><\/a><\/p>\n<p>Note that in both cases we added\u00a0<strong>two<\/strong> equivalents of our Grignard reagent to the ester, forming a tertiary alcohol.<\/p>\n<p><strong>Wait a minute &#8211; how did this happen?!<\/strong><\/p>\n<h2><a id=\"five\"><\/a>5. Why Is There &#8220;Double Addition&#8221;With Esters? The Mechanism<\/h2>\n<p>This reaction incorporates the second most important mechanism of carbonyls (next to &#8220;addition&#8221;), namely, &#8220;<a href=\"https:\/\/www.masterorganicchemistry.com\/2010\/05\/21\/lets-talk-about-the-12-elimination\/\">elimination<\/a>&#8220;. In fact &#8220;elimination&#8221; is the exact reverse of &#8220;addition&#8221; ! Let&#8217;s walk through it. There are 4 steps<\/p>\n<ul>\n<li>In the <strong>first step<\/strong>,\u00a0\u00a0the Grignard performs an <strong>addition<\/strong> reaction on the ester, forming C-C and breaking C-O (pi), giving us an intermediate with a negatively charged oxygen. We&#8217;ve seen this type of reaction before in the addition of Grignards to aldehydes and ketones.<\/li>\n<li>Now comes the new step:<strong> elimination <\/strong>(sometimes, &#8220;1,2 elimination&#8221;).\u00a0This intermediate has a reasonably good\u00a0<strong>leaving group\u00a0<\/strong>(OCH<sub>2<\/sub>CH<sub>3<\/sub> in the case below). What happens next is reformation of the C-O pi bond with expulsion\u00a0of the leaving group (CH<sub>3<\/sub>CH<sub>2<\/sub>O<sup>\u2013<\/sup> in the case below). In other words, we form C\u2013O \u03c0 and break a C\u2013O single bond. \u00a0The new product is a\u00a0<strong>ketone.<\/strong><\/li>\n<\/ul>\n<p>Together, these two steps are often referred to as Nucleophilic Acyl Substitution (<a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/05\/06\/nucleophilic-acyl-substitution\/\"><em>See post: Nucleophilic Acyl Substitution<\/em><\/a>)<\/p>\n<p>Elimination does not occur in addition to aldehydes and ketones because the leaving group would have to be the extremely strong bases H(-) or R(-). It is reasonably favorable for esters because the leaving group RO(-) is of comparable basicity to the negatively charged oxygen of the tetrahedral intermediate. \u00a0[<a href=\"#noteone\">Note 1<\/a>]<\/p>\n<ul>\n<li><strong>But wait! There&#8217;s more!\u00a0<\/strong>After Step 2, we have a new ketone. As we&#8217;ve seen before, Grignards will react quickly with ketones in yet another\u00a0<strong>addition reaction\u00a0<\/strong>[Step 3]. Here, as in Step 1, we form C\u2013C and break C\u2013O (pi).\u00a0The result is a tertiary alkoxide (the conjugate base of a tertiary alcohol).<\/li>\n<\/ul>\n<p><span style=\"color: #993366;\"><em>[Wait, you might ask. If we just use one equivalent of Grignard reagent, is it possible to get the reaction to stop at the ketone stage? The short answer is &#8220;no&#8221;. [See <a style=\"color: #993366;\" href=\"#notethree\">Note 3<\/a>\u00a0for the long answer]]<\/em><\/span><\/p>\n<ul>\n<li>Finally, <strong>protonation<\/strong> of this tertiary alkoxide yields the tertiary alcohol (<strong>Step 4).\u00a0<\/strong><\/li>\n<\/ul>\n<p>Here&#8217;s the graphical walkthrough:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15340\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/8-mechanism-for-the-double-addition-of-grignard-reagents-to-esters-1.gif\" alt=\"mechanism for the double addition of grignard reagents to esters\" width=\"600\" height=\"506\" \/><\/p>\n<h2><strong><a id=\"six\"><\/a>6. Summary: Reactions of Grignard Reagents<\/strong><\/h2>\n<p>That does it for the key reactions of Grignard reagents you&#8217;ll see in most Org 1 and Org 2 courses.<\/p>\n<p>In the next post we&#8217;ll talk about yet another way to screw up formation of Grignard reagents, and it involves the reactions in this post.<\/p>\n<p><strong>Next Post: <a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/12\/16\/protecting-groups-in-grignard-reactions\/\">Protecting Groups In Grignard Reactions<\/a><\/strong><\/p>\n<hr \/>\n<h2><strong><a id=\"notes\"><\/a>Notes<\/strong><\/h2>\n<div class=\"related-articles\"><p><strong>Related Articles<\/strong><\/p><ul><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2022\/09\/09\/nucleophilic-addition\/\" class=\"\"><span>Nucleophilic Addition To Carbonyls<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/05\/06\/nucleophilic-acyl-substitution\/\" class=\"\"><span>Nucleophilic Acyl Substitution (With Negatively Charged Nucleophiles)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/12\/16\/protecting-groups-in-grignard-reactions\/\" class=\"\"><span>Protecting Groups In Grignard Reactions<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/01\/13\/synthesis-using-grignard-reagents-1\/\" class=\"\"><span>Grignard Practice Problems: Synthesis (1)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/01\/19\/grignard-reactions-and-synthesis-2\/\" class=\"\"><span>Grignard Reactions And Synthesis (2)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/02\/05\/gilman-reagents-organocuprates-what-theyre-used-for\/\" class=\"\"><span>Gilman Reagents (Organocuprates): What They\u2019re Used For<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/04\/11\/reaction-map-reactions-of-organometallics\/\" class=\"\"><span>Reaction Map: Reactions of Organometallics<\/span><\/a><\/li><\/ul><\/div>\n<p><a id=\"noteone\"><\/a><strong>Note 1:<\/strong> Although alkoxides (RO<sup>\u2013<\/sup>, the conjugate base of alcohols, pK<sub>a<\/sub> 16-18) are not on anyone&#8217;s list of Great Leaving Groups, they are some 25 orders of magnitude better leaving groups than hydrides (H\u2013, the conjugate base of hydrogen, pK<sub>a<\/sub> 40) and more than 30 orders of magnitude better than alkyl groups (R- , the conjugate base of alkanes, pK<sub>a<\/sub> 50). Thus, when the alkoxide intermediate is formed in Step 1, there is not any deep energetic penalty for the C-O pi bond to reform and for RO- to be expelled: after all, we are simply replacing a strong base (the O- ) with one of comparable basicity.<\/p>\n<p><a id=\"notetwo\"><\/a>\u00a0<strong>Note 2.\u00a0<\/strong> Why are ketones more reactive towards Grignard reagents than esters? This requires understanding the phenomenon of <a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/12\/15\/exploring-resonance-pi-donation\/\">pi donation<\/a>. The lone pair on oxygen donates electron density into the carbonyl carbon. This is worthy of a separate post, but here&#8217;s the bottom line:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15341\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/F1-Pi-donation-means-that-esters-are-less-reactive-towards-grignards-than-ketones-and-aldehydes-1.gif\" alt=\"Pi donation means that esters are less reactive towards grignards than ketones and aldehydes\" width=\"600\" height=\"496\" \/><\/p>\n<p><a id=\"notethree\"><\/a><strong>Note 3.<\/strong> Alas, no. Using 1 equivalent of Grignard will result in 0.5 equivalents of a tertiary alcohol and 0.5 equivalents of the starting ester. The reason why is that Step 2 [elimination] is quite fast!<\/p>\n<p>Once elimination occurs, we will have ketone in the presence of an ester. For interesting reasons [see <a href=\"#hotetwo\">Note 2<\/a>] ketones are more reactive than esters toward Grignard reagents, which means they will be consumed more quickly.<\/p>\n<hr \/>\n<h2><a id=\"quizzes\"><\/a>Quiz Yourself!<\/h2>\n<p><div class=\"wq-quiz-wrapper\" data-id=\"38826\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"38826\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-font-color: #444;\n}\n\n\t\t\t.wq-quiz-wrapper[data-id=\"38826\"] {\n\t\t\t\t--wq-question-width: 600px;\n\t\t\t}\n\n\t\t\t@media screen and (max-width: 600px) {\n\t\t\t\t.wq-quiz-wrapper[data-id=\"38826\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-38826\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-38826 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"38826\">\n<div 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aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1473-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0581-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1477-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1478-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1461-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><br \/>\n<br \/>\n<img loading=\"lazy\" decoding=\"async\" class=\"wp-image-36214 aligncenter\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/1463-Front-Image-Only.png\" alt=\"\" width=\"600\" height=\"450\" \/><\/a><\/p>\n<p style=\"text-align: center;\"><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a MOC member<\/strong><\/a> to see the clickable quiz with answers on the back.<\/p>\n<p><\/p>\n<hr \/>\n<h2><strong><a id=\"references\"><\/a>(Advanced) References and Further Reading:<\/strong><\/h2>\n<ol>\n<li><strong>The Grignard Reagents<br \/>\n<\/strong>Dietmar Seyferth<br \/>\n<cite>Organometallics<\/cite>\u00a0<strong>2009<\/strong>\u00a0<em>28<\/em> (6), 1598-1605<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/om900088z\">10.1021\/om900088z<\/a><br \/>\nA historical overview on Grignard reagents by the late Prof. Dietmar Seyferth (MIT), founding editor of the journal <em>Organometallics.\u00a0<\/em><\/li>\n<li><strong>Secondary and Tertiary Alkyllithium Compounds and Some Interconversion Reactions with Them<br \/>\n<\/strong>Henry Gilman, Fred W. Moore, and Ogden Baine<strong><br \/>\n<\/strong><em>Journal of the American Chemical Society<\/em><strong> 1941, <\/strong><em>63<\/em> (9), 2479-2482<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01854a046\">1021\/ja01854a046<\/a><br \/>\nProf. Henry Gilman (Iowa State) was a pioneer in organometallic chemistry in the first half of the 20<sup>th<\/sup> century. In this paper he describes the synthesis and reactivity of various alkyllithiums (<em>n<\/em>-butyllithium, <em>s<\/em>-butyllithium, isopropyllithium, and <em>t<\/em>-butyllithium). The synthesis is from the alkyl halide and lithium metal, as can be seen in the experimental section.<\/li>\n<li><strong>t-Butyllithium<br \/>\n<\/strong>Paul D. Bartlett, C. Gardner Swain, and Robert B. Woodward<br \/>\n<em>Journal of the American Chemical Society<\/em> <strong>1941,<\/strong> <em>63<\/em> (11), 3229-3230<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja01856a501\">1021\/ja01856a501<\/a><br \/>\nThis communication is from some legendary figures in organic chemistry and describes the preparation of <em>t-<\/em>butyllithium.<\/li>\n<li><strong>2-PHENYLPYRIDINE<br \/>\n<\/strong> C. W. Evans and C. F. H. Allen<br \/>\n<em>Org. Synth.<\/em> <strong>1938<\/strong>, <em>18<\/em>, 70<br \/>\n<strong>DOI:<\/strong> <a href=\"http:\/\/orgsyn.org\/demo.aspx?prep=CV2P0517\">10.15227\/orgsyn.018.0070<\/a><br \/>\nThe first step in this procedure is a preparation of phenyllithium from bromobenzene and lithium metal. <em>Organic Syntheses<\/em> is a reputable source of reproducible and independently tested synthetic organic procedures.<\/li>\n<li><strong>The mechanism of the lithium &#8211; halogen Interchange reaction : a review of the literature<br \/>\n<\/strong>Bailey, W. F.; Patricia, J. J.<strong><br \/>\n<\/strong><em> Organomet. Chem.<\/em><strong> 1988, <\/strong><em>352<\/em> (1-2), 1-46<strong><br \/>\nDOI: <\/strong><a href=\"https:\/\/www.sciencedirect.com\/science\/article\/pii\/0022328X88830171\">10.1016\/0022-328X(88)83017-1<\/a><strong><br \/>\n<\/strong>In modern organic chemistry, organolithium reagents are rarely prepared from scratch (i.e. using Li metal), due to the ready availability of alkyllithium reagents from vendors (e.g. MeLi, the BuLi reagents, PhLi, etc.). Instead, these reagents can be used to form other organolithium species through a process known as <em>lithium-halogen exchange.<\/em><\/li>\n<li><strong>What\u2019s Going on with These Lithium Reagents?<br \/>\n<\/strong>Hans J. Reich<strong><br \/>\n<\/strong><em>The Journal of Organic Chemistry<\/em><strong> 2012, <\/strong><em>77<\/em> (13), 5471-5491<br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo3005155\">1021\/jo3005155<\/a><br \/>\nProf. Hans Reich (U. Wisconsin-Madison) has spent his career studying the behavior of organolithium species, and this is an account of his research and the surprising findings he made. This is classic Physical Organic chemistry.<\/li>\n<\/ol>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>All About The Reactions of Grignard Reagents Grignard reagents are excellent carbon-based nucleophiles as well as strong bases. They will add to aldehydes and ketones <\/p>\n","protected":false},"author":1,"featured_media":38803,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1102],"tags":[294,470,215,347],"post_folder":[],"class_list":["post-9320","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-organometallics","tag-addition","tag-epoxides","tag-grignards","tag-organometallics"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Reactions of Grignard Reagents &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"Reactions of Grignard reagents with epoxides, aldehydes, ketones, esters, and acid, plus the mechanism for why Grignards add twice to esters.\" \/>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.masterorganicchemistry.com\/2015\/12\/10\/reactions-of-grignard-reagents\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Reactions of Grignard Reagents &#8211; 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