{"id":9266,"date":"2015-10-28T14:26:04","date_gmt":"2015-10-28T18:26:04","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=9266"},"modified":"2022-11-02T04:59:32","modified_gmt":"2022-11-02T09:59:32","slug":"whats-an-organometallic","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2015\/10\/28\/whats-an-organometallic\/","title":{"rendered":"What&#8217;s An Organometallic?"},"content":{"rendered":"<p><strong>What Is The Definition of An Organometallic Compound?<\/strong><\/p>\n<ul>\n<li>In many of the functional groups in organic chemistry, carbon is attached to a more electronegative element, giving it a partial positive charge and electrophilic character<\/li>\n<li>However when carbon is attached to a less electronegative element &#8211; metals, in particular &#8211; it will have a partial\u00a0<strong>negative\u00a0<\/strong>charge and have nucleophilic character<\/li>\n<li>Molecules which contain a carbon-metal bond are known as\u00a0<strong>organometallic\u00a0<\/strong>compounds<\/li>\n<li>Examples of organometallic compounds include organolithium compounds, organomagnesium compounds (Grignard reagents) and organocuprates (Gilman reagents)<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-15299\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/0-summary-what-is-an-organometallic-has-carbon-metal-bond-carbon-has-higher-electronegativity.gif\" alt=\"summary - what is an organometallic - has carbon metal bond carbon has higher electronegativity\" width=\"630\" height=\"353\" \/><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li><a href=\"#one\">A Refresher on &#8220;Dipoles&#8221;<\/a><\/li>\n<li><a href=\"#two\">Dipoles Provide A Clue To Reactivity<\/a><\/li>\n<li><a href=\"#three\">Some Examples Of How Dipoles Govern Reactivity<\/a><\/li>\n<li><a href=\"#four\">Organometallics: Contain Carbon-Metal Bonds (And Have Nucleophilic Carbons!)<\/a><\/li>\n<li><a href=\"#five\">Summary: Organometallics<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<\/ol>\n<hr \/>\n<h2><a id=\"one\"><\/a>1. Some Background On Dipoles<\/h2>\n<p>It&#8217;s hard to underestimate\u00a0how important <strong>dipoles<\/strong> are in determining the reactivity of a molecule.<\/p>\n<p>Wait: <em>dipoles<\/em>, you might ask. <em>H<\/em><em>ow do we determine a dipole again?\u00a0<\/em><\/p>\n<p>Let&#8217;s start this series by making sure we&#8217;re clear on this, because it will be key to understanding the class of molecules we call &#8220;organometallics&#8221;.<\/p>\n<p>Recall that molecules are built of covalent bonds between atoms, but the electrons in covalent bonds\u00a0aren&#8217;t always shared equally between atoms.<\/p>\n<ul>\n<li>When two atoms of significantly different electronegativity form a covalent bond, the atom with higher electronegativity (&#8220;greedier&#8221; for electrons, if you&#8217;ll pardon the anthropomorphism) will have an unequal share of those electrons, leading to a partial buildup of negative charge on that atom (which we represent by using the symbol \u03b4<sup>&#8211;\u00a0<\/sup>).<\/li>\n<li>Conversely, the atom with the lower negativity will have a partial deficit of electron density, leading to a partial positive charge (\u03b4<sup>+<\/sup>).<\/li>\n<li>The most likely place to find a large dipole is to look for strongly electronegative atoms such as oxygen (3.5) and nitrogen (3.0) or the halogens fluoride (4.0), chlorine (3.2) and bromine (3.0): if any of those atoms is bound to a less electronegative atom like carbon (2.6) or hydrogen (2.2), a dipole results.<\/li>\n<\/ul>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15307\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/1-dipoles-arise-when-bonds-form-between-atoms-with-different-electronegativity-electronegativity-list-of-elements-partial-charges-1.gif\" alt=\"dipoles arise when bonds form between atoms with different electronegativity electronegativity list of elements partial charges\" width=\"630\" height=\"340\" \/><\/p>\n<p>Since <strong>opposite charges attract<\/strong>, atoms which are electron rich (\u03b4<sup>&#8211;\u00a0<\/sup>) are attracted to atoms bearing partial positive charge\u00a0(\u03b4<sup>+<\/sup>).<\/p>\n<p>You\u2019ve likely already seen that <strong>molecules with large dipoles<\/strong> (so-called, &#8220;polar&#8221; molecules) tend to have <strong>higher<\/strong> boiling points and melting points than molecules of similar molecular weight without them (&#8220;non-polar&#8221; molecules).<\/p>\n<p>That&#8217;s because attractive interactions between oppositely charged dipoles\u00a0(e.g. hydrogen bonds and dipole-dipole interactions) require additional energy to disrupt.<\/p>\n<h2><a id=\"two\"><\/a>2. More Background: Using Dipoles To Understand Reactive Sites<\/h2>\n<p>Another feature of dipoles, less often\u00a0mentioned, is that they provide us with excellent hypotheses for determining where reactions might happen between two given molecules.<\/p>\n<p>If you&#8217;ve started to cover even the simplest of reactions, you&#8217;ve already learned that bonds are formed when a Lewis base (electron rich) donates a pair of electrons to a Lewis acid (electron poor).<\/p>\n<ul>\n<li>When the electron pair is being donated to any atom except hydrogen, we usually call that Lewis base a &#8220;nucleophile&#8221; [when a lone pair is being donated to hydrogen, we tend to call it a &#8220;base&#8221;].<\/li>\n<li>Since\u00a0atomic nuclei are\u00a0positively charged, &#8220;nucleophile&#8221; is shorthand for \u00a0&#8220;positive-charge loving&#8221;. Nothing new here:\u00a0atoms which are\u00a0(\u03b4<sup>&#8211;\u00a0<\/sup>) are attracted to atoms which are\u00a0(\u03b4<sup>+<\/sup>).<\/li>\n<\/ul>\n<p>On the other hand, since Lewis acids tend to be electron poor (\u03b4<sup>+<\/sup>, negative-charge-loving) and they are attracted to electrons [or to be more specific, atoms with high electron density (\u03b4<sup>&#8211;\u00a0<\/sup>) ], we often call Lewis acids &#8220;electrophiles&#8221;.<\/p>\n<p><strong>To shorten it to a point, pretty much every reaction you&#8217;ll learn is some version of nucleophile (negative charge) attacks electrophile (positive charge)<\/strong>. And learning to recognize dipoles will help you to recognize nucleophiles and electrophiles.<\/p>\n<p>This diagram tries to show some interactions between potential nucleophiles and electrophiles based solely on dipoles. Note that this <strong>doesn&#8217;t mean that reactions between these atoms will necessarily occur &#8211; <\/strong>it&#8217;s only saying\u00a0that these are good guesses for where the &#8220;action&#8221; will be.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-15302\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/3-reactions-generally-occur-between-oppositely-charged-dipoles-partial-positive-and-partial-negative-like-charges-repel-opposite-charges-attract.gif\" alt=\"reactions generally occur between oppositely charged dipoles partial positive and partial negative like charges repel opposite charges attract\" width=\"600\" height=\"416\" \/><\/p>\n<h2><a id=\"three\"><\/a>3. Examples With Reactions<\/h2>\n<p>Just to illustrate, here are some examples of <em>real<\/em>\u00a0<em>reactions\u00a0<\/em> you see in Org 1 (or sometimes Org 2)\u00a0which follow this pattern. Note how the <strong>source of electrons<\/strong> (the tail of the blue arrow &#8211; the <strong>nucleophile<\/strong>) is always the <strong>negative<\/strong> end of a dipole, and the <strong>electron acceptor<\/strong> (the head of the blue arrow &#8211; the <strong>electrophile<\/strong>) always the <strong>positive<\/strong> end of a dipole. Nucleophile attacks electrophile.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15303\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/4-examples-of-dipole-attraction-in-organic-reactions-sn2-thiol-alkyl-chloride-epoxide-opening-alkoxide-addition-to-aldehyde-with-nabh4.gif\" alt=\"examples of dipole attraction in organic reactions sn2 thiol alkyl chloride epoxide opening alkoxide addition to aldehyde with nabh4\" width=\"600\" height=\"481\" \/><\/p>\n<p>There&#8217;s one trick &#8211; see that last example? The boron bears a negative formal charge (BH<sub>4<\/sub><sup>\u2013<\/sup>) but the hydrogen acts as a nucleophile. What&#8217;s going on there?<\/p>\n<p>Here, the trick is to see that hydrogen actually has a higher electronegativity (2.2) than boron (2.0) and therefore in the B-H bond, it&#8217;s the hydrogen which is \u00a0\u03b4<sup>&#8211;\u00a0<\/sup>. Always pay attention to the dipole more than the formal charge, <strong>because formal charge can mislead.<\/strong><\/p>\n<h2><a id=\"organomet\"><\/a>4. <a id=\"four\"><\/a>Organometallics Are Molecules That Contain a Carbon-Metal Bond<\/h2>\n<p>All of this should be review. However, like a dog who needs to walk around their pillow before they finally lie down, sometimes teachers\u00a0need to get the introduction out of the way before getting deep into a topic.<\/p>\n<p>The reason I began with\u00a0dipoles is the following. Most of the functional groups you&#8217;ll encounter in organic chemistry have one feature in common. Look for the biggest dipole in these functional groups.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15304\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/5-many-functional-groups-have-carbon-bonded-to-more-electronegative-element-so-carbon-is-electrophilic-reacts-with-nucleophiles.gif\" alt=\"many functional groups have carbon bonded to more electronegative element so carbon is electrophilic reacts with nucleophiles\" width=\"600\" height=\"271\" \/><\/p>\n<p>Do you notice that in all of these cases, <strong>carbon is electropositive<\/strong> [electron poor]? We see carbon as an electrophile <em>so often<\/em> in introductory organic chemistry,<strong> it&#8217;s important to realize that carbon can act as a\u00a0<em>nucleophile<\/em> as well.<\/strong><\/p>\n<p>If carbon tends to be electrophilic when attached to a more electronegative group, then under what circumstances might carbon act as a nucleophile?<\/p>\n<p><strong>When it&#8217;s attached to a less electronegative atom!<\/strong>\u00a0After all, carbon is slightly upper-middle class when it comes to electronegativity (2.6). There&#8217;s a lot of other elements on the periodic table with lower electronegativities than that. Many of them are <strong>metals<\/strong> of some variety, whether they be alkali metals, alkaline earth metals, or transition metals. Even group 13 elements (the old group III) &#8211; boron, aluminum and so on &#8211; qualify as metals for these purposes.<\/p>\n<p>Molecules that contain a carbon-metal bond are referred to as <strong>organometallics<\/strong>.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15305\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/6-organometallic-carbon-is-bonded-to-less-electronegative-element-and-carbon-has-partial-negative-charge-and-is-therefore-nucleophilic.gif\" alt=\"organometallic carbon is bonded to less electronegative element and carbon has partial negative charge and is therefore nucleophilic\" width=\"600\" height=\"164\" \/><\/p>\n<p>The\u00a0common theme in organometallic chemistry is that<strong> carbon tends to act as a nucleophile\u00a0<\/strong>(or a base, if there are Br\u00f8nsted acids around).<\/p>\n<p>We&#8217;ll get to some examples of reactions in subsequent posts, but first, let&#8217;s just see some examples of what organometallic compounds look like. Three of them are extremely common in introductory organic chemistry. Organolithium compounds, organomagnesium compounds (which go by the name &#8220;Grignard reagents&#8221; after their discoverer), and organocuprate reagents (again, usually referred to as &#8220;Gilman&#8221; reagents after the chemist who first popularized them, <strong>Henry<\/strong><strong> Gilman<\/strong> of Iowa State University).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-15306\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2019\/12\/7-common-examples-of-organometallic-compounds-include-organolithium-grignard-reagents-gilman-reagents-organocuprates-all-excellent-nucleophiles.gif\" alt=\"common examples of organometallic compounds include organolithium grignard reagents gilman reagents organocuprates all excellent nucleophiles\" width=\"600\" height=\"290\" \/><\/p>\n<h2><a id=\"five\"><\/a>5. Summary: Organometallic Compounds<\/h2>\n<p>There are, of course, <i>many<\/i> more examples of organometallic compounds &#8211; this is just a dusting of snow on the tip of the iceberg &#8211; but for our purposes, these three classes of organometallic compound will carry most of the freight.<\/p>\n<p>In the next post, we&#8217;ll show some examples of <strong>how these organometallic compounds are made<\/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\/2015\/11\/09\/synthesis-of-grignard-and-organolithium-reagents\/\" class=\"\"><span>Formation of Grignard and Organolithium Reagents<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/11\/13\/organometallics-are-strong-bases\/\" class=\"\"><span>Organometallics Are Strong Bases<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2016\/01\/29\/gilman-reagents-organocuprates-how-theyre-made\/\" class=\"\"><span>Organocuprates (Gilman Reagents): How They\u2019re Made<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2015\/12\/10\/reactions-of-grignard-reagents\/\" class=\"\"><span>Reactions of Grignard Reagents<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2012\/02\/22\/common-mistakes-formal-charges-can-mislead\/\" class=\"\"><span>Common Mistakes: Formal Charges Can Mislead<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/11\/15\/how_to_use_electronegativity\/\" class=\"\"><span>How To Use Electronegativity To Determine Electron Density (and why NOT to trust formal charge)<\/span><\/a><\/li><\/ul><\/div>\n<p><strong>Note 1<\/strong>. This series will only go into the most superficial aspects of organometallic compounds and their reactions. For much more thorough treatment, I strongly encourage you to visit <strong><a href=\"https:\/\/organometallicchem.wordpress.com\">The Organometallic Reader<\/a><\/strong> by Mike Evans, a free online resource that teaches the essentials of this very deep subject.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>What Is The Definition of An Organometallic Compound? In many of the functional groups in organic chemistry, carbon is attached to a more electronegative element, <\/p>\n","protected":false},"author":1,"featured_media":15299,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1102],"tags":[495,1081,215,1080,347],"post_folder":[],"class_list":["post-9266","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-organometallics","tag-dipoles","tag-gilman","tag-grignards","tag-organolithiums","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>What&#039;s An Organometallic? &#8211; Master Organic Chemistry<\/title>\n<meta name=\"description\" content=\"Organometallic compounds contain a carbon-metal bond, and as carbon has a higher electronegativity than metals, carbon is nucleophilic in these species.\" \/>\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\/10\/28\/whats-an-organometallic\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"What&#039;s An Organometallic? 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