{"id":1944,"date":"2011-08-19T08:43:58","date_gmt":"2011-08-19T13:43:58","guid":{"rendered":"https:\/\/www.masterorganicchemistry.com\/?p=1944"},"modified":"2026-04-30T13:15:37","modified_gmt":"2026-04-30T18:15:37","slug":"lindlars-catalyst-partial-cis-reduction","status":"publish","type":"post","link":"https:\/\/www.masterorganicchemistry.com\/2011\/08\/19\/lindlars-catalyst-partial-cis-reduction\/","title":{"rendered":"Partial Reduction of Alkynes With Lindlar&#8217;s Catalyst"},"content":{"rendered":"<p><strong>Partial Reduction of Alkynes to cis Alkenes with the Lindlar Catalyst<\/strong><\/p>\n<ul>\n<li><strong>Alkynes<\/strong> are generally more reactive towards catalytic hydrogenation (e.g. Pd-C, H<sub>2<\/sub>) than <strong>alkenes\u00a0<\/strong><\/li>\n<li>While it&#8217;s <em>possible<\/em> to partially hydrogenate an alkyne to an alkene by limiting the number of equivalents of hydrogen gas, it&#8217;s not very <em>convenient (<span style=\"color: #999999;\">since it requires equpiment such as a gas buret, and is impractical to do on small scales<\/span><\/em>).<\/li>\n<li>An alternative approach is to make the Pd-catalyst less active for hydrogenation by &#8220;poisoning&#8221; it, often with lead salts (Pb) and amines (such as quinoline). The combination of Pd supported on calcium carbonate (CaCO<sub>3<\/sub>) that has been treated with a small amount of lead (often Pb(OAc)<sub>2<\/sub> ) is known as &#8220;<strong>Lindlar&#8217;s catalyst&#8221;<\/strong>.<\/li>\n<li>Lindlar&#8217;s catalyst always gives <strong>cis<\/strong> alkenes from alkynes. Alkenes are <strong>not<\/strong> hydrogenated.<\/li>\n<li>Alternative reagents that are equivalent to Lindlar&#8217;s catalyst include Pd on barium sulfate (Pd\/BaSO<sub>4<\/sub>) with quinoline, as well as nickel boride (Ni<sub>2<\/sub>B).<\/li>\n<li><strong>The stereochenistry of this reaction is very commonly tested in exams,\u00a0<\/strong>expecially in combination with reactions of alkenes that are also stereospecific (e.g. halogenation, dihydroxylation).<\/li>\n<li>Note that it&#8217;s also possible to partially reduce alkynes to <em>trans<\/em>-alkenes through the use of sodium in ammonia (Na\/NH<sub>3<\/sub>) &#8211; <span style=\"color: #993366;\"><em>See article &#8211; <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2013\/05\/08\/lindlar-nanh3-partial-reduction-of-alkynes\/\">Partial Reduction of Alkynes to Trans Alkenes<\/a><\/em><\/span>)<\/li>\n<\/ul>\n<p><img fetchpriority=\"high\" decoding=\"async\" class=\"alignnone wp-image-35853\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/12\/0-summary-lindlar-catalyst-for-partial-reduction-of-alkynes-to-give-cis-alkenes.gif\" alt=\"summary-lindlar catalyst for partial reduction of alkynes to give cis alkenes\" width=\"640\" height=\"530\" \/><\/a><\/p>\n<p><strong>Table of Contents<\/strong><\/p>\n<ol>\n<li style=\"list-style-type: none;\">\n<ol>\n<li><a href=\"#one\">Partial Hydrogenation of Alkynes to Alkenes With Lindlar&#8217;s Catalyst<\/a><\/li>\n<li><a href=\"#two\">Examples of Partial Reduction<\/a><\/li>\n<li><a href=\"#three\">Applications of Lindlar&#8217;s Catalyst<\/a><\/li>\n<li><a href=\"#four\">Using Lindlar&#8217;s Catalyst in Synthesis<\/a><\/li>\n<li><a href=\"#five\">Summary<\/a><\/li>\n<li><a href=\"#notes\">Notes<\/a><\/li>\n<li><a href=\"#quiz\">Quiz Yourself!<\/a><\/li>\n<li><a href=\"#references\">(Advanced) References and Further Reading<\/a><\/li>\n<\/ol>\n<\/li>\n<\/ol>\n<hr \/>\n<h2><a id=\"one\"><\/a>1. Partial Hydrogenation of Alkynes to Alkenes With Lindlar&#8217;s Catalyst<\/h2>\n<p>We&#8217;ve seen that\u00a0<strong>catalytic hydrogenation<\/strong> is a useful reaction for converting alkenes into alkanes.\u00a0\u00a0[<span style=\"color: #993366;\"><em>See article: <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2011\/11\/25\/palladium-on-carbon-pdc\/\">Catalytic Hydrogenation of Alkenes<\/a><\/em><\/span>]<\/p>\n<p>In catalytic hydrogenation, hydrogen gas is adsorbed onto the surface of a &#8220;late&#8221; metal (<span style=\"color: #993366;\"><em>usually palladium or platinum<\/em><\/span>) that has been dispersed on a high surface-area material such as activated carbon.<\/p>\n<p>Alkenes and other unsaturated molecules readily bind to late metals through their pi-bonds. When an alkene lands on a metal packed with hydrogen on its surface, an<strong> addition reaction<\/strong> occurs where two new C-H bonds are formed and a C-C pi bond is broken, generally with <strong><em>syn<\/em><\/strong> stereoselectivity. This produces an alkane.<\/p>\n<p>When alkynes are used in place of alkenes in the presence of Pd-C and H<sub>2<\/sub>, <strong>both\u00a0<\/strong>double bonds are hydrogenated, also resulting in an <strong>alkane<\/strong>:<\/p>\n<p><span style=\"color: #993366;\"><em>This reaction is often referred to as a &#8220;reduction&#8221; since the oxidation state of carbon is lowered during this process<\/em><\/span> (<span style=\"color: #993366;\"><em>oxidation state of each carbon in the neutral alkyne is zero; oxidation state of each carbon in the alkane is -2.\u00a0 <\/em><a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2011\/07\/25\/calculating-the-oxidation-state-of-a-carbon\/\"><em>See article &#8211; Calculating the Oxidation State of Carbon<\/em><\/a>).\u00a0<\/span><\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-35845\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/12\/1-alkynes-can-be-hydrogenated-to-alkanes-with-pd-c-and-excess-hydrogen-1.gif\" alt=\"alkynes can be hydrogenated to alkanes with pd c and excess hydrogen\" width=\"640\" height=\"371\" \/><\/a><\/p>\n<p>Forgive me for my lack of excitement, but I think the proper reaction to this particular reaction is, &#8220;big whoop&#8221;.<\/p>\n<p>I mean, making alkanes from alkanes is fine if your plan is to make margarine or something.\u00a0 But from a chemical synthesis perspective, it&#8217;s a waste of a potentially useful functional group.<\/p>\n<p>Why? Well, we&#8217;ve just seen that acetylide ions are extremely useful for making C-C bonds through reaction (S<sub>N<\/sub>2) with alkyl halides.\u00a0 (<span style=\"color: #993366;\"><em><span style=\"color: #993366;\">See article &#8211; <\/span><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/05\/01\/the-2-most-important-reactions-of-alkynes\/\"><span style=\"color: #993366;\">Substitution Reactions of Acetylides<\/span><\/a><\/em><\/span>). For the first time, this gave us a method for building up longer carbon chains from smaller ones.<\/p>\n<p>Using this reaction just for making longer alkanes isn&#8217;t exactly exciting because there aren&#8217;t that many interesting reactions of alkanes aside from 1) free-radical substitution, which we&#8217;ve seen is a pretty poorly selective reaction, (<a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/09\/23\/selectivity-in-free-radical-reactions\/\">link<\/a>), and 2) combustion, which kind of defeats the whole point of synthesis in the first place.<\/p>\n<p>You know what\u00a0<strong>is<\/strong> exciting, though? Reactions of <strong>a<\/strong><strong>lkenes.\u00a0<\/strong><\/p>\n<p>It would be really useful to get our alkyne to accept only <strong>one<\/strong> equivalent of H<sub>2. <\/sub>Then we&#8217;d have an <strong>alkene<\/strong>, and we&#8217;d unlock the many useful reactions of alkenes we&#8217;ve learned previously. [<span style=\"color: #993366;\"><em>See Article &#8211; <a style=\"color: #993366;\" href=\"https:\/\/www.masterorganicchemistry.com\/2014\/01\/21\/synthesis-reactions-of-alkenes\/\">Reaction Map of Alkenes<\/a> to give you a fuller perspective] <\/em><\/span> This would allow us to build in all kinds of functional groups &#8211; alcohols, alkyl halides, epoxides, and many more &#8211; that just aren&#8217;t readily available from boring ol&#8217; alkanes. [<a href=\"#noteone\"><span style=\"color: #ff0000;\">Note 1<\/span><\/a>]<\/p>\n<p>As it turns out, alkynes are more reactive towards hydrogenation than alkenes. It <strong>is<\/strong> possible to get an alkyne to accept just one equivalent of H<sub>2<\/sub>,\u00a0<strong>if<\/strong> one is very careful with doling out a single molar equivalent using a gas buret or similar.<\/p>\n<p><img decoding=\"async\" class=\"alignnone wp-image-35846\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/12\/2-alkynes-can-be-partially-hydrogenated-to-alkenes-with-pd-C-and-1-1.gif\" alt=\"alkynes can be partially hydrogenated to alkenes with pd-C and\" width=\"640\" height=\"311\" \/><\/a><\/p>\n<p>Note that while I say it is <em>possible<\/em>, it&#8217;s not actually all that\u00a0<em>convenient<\/em>, since you need to set up an additional piece of equipment, and furthermore it can be tricky to accurately measure out one molar equivalent of H<sub>2<\/sub> on small scale.<\/p>\n<p>A simpler alternative for partial hydrogenation is\u00a0just to <strong>make the catalyst worse.\u00a0<\/strong><\/p>\n<p><em>Wait, what?<\/em><\/p>\n<p>Yes, make it worse. Since alkynes are already more reactive than alkenes, just <strong>poison\u00a0<\/strong>the catalyst enough so that is unable to carry out the hydrogenation of alkenes. Problem solved!<\/p>\n<p>The most commonly used &#8220;poisoned&#8221; catalyst is Lindlar&#8217;s catalyst, which is a mixture of palladium, calcium carbonate, and traces of lead (Pb). Quinoline, an aromatic amine, is sometimes added to help with selectivity. . [<em><span style=\"color: #993366;\">Described in more detail <a style=\"color: #993366;\" href=\"#refthree\">here<\/a>\u00a0<strong><a href=\"#notetwo\">Note 2<\/a>].\u00a0<\/strong><\/span><\/em><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35854\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2011\/08\/3-lindlars-catalyst-is-a-mix-of-palladium-quinoline-and-lead-carbonate-selective-for-partial-hydrogenation-of-alkynes.gif\" alt=\"lindlars catalyst is a mix of palladium quinoline and lead carbonate - selective for partial hydrogenation of alkynes\" width=\"640\" height=\"589\" \/><\/a><\/p>\n<p>The &#8220;poisons&#8221; here are a lead (Pb) and\u00a0amine [quinoline].\u00a0<span style=\"color: #993366;\"><em> It is thought that lead (Pb) acts to reduce the bonding of H<sub>2<\/sub> to the metal, while the amine (quinoline) helps to avoid unwanted byproducts. (<a style=\"color: #993366;\" href=\"#reffour\">See reference here<\/a>)<\/em><\/span><\/p>\n<p>Another reagent that sometimes sees use is nickel boride (&#8220;Ni<sub>2<\/sub>B&#8221;), which for our purposes can be considered to be equivalent to Lindlar&#8217;s catalyst. It is used in the presence of hydrogen gas. [<a href=\"#notethree\"><span style=\"color: #ff0000;\">Note 3<\/span><\/a>]<\/p>\n<h2><a id=\"two\"><\/a>2. Lindlar&#8217;s Catalyst: Examples<\/h2>\n<p>One advantage of Lindlar&#8217;s catalyst is that it is selective for the reduction of alkynes.\u00a0 Alkenes are not affected. The stereochemistry of the alkene produced is always <em>cis<\/em>.<\/p>\n<p>Furthermore, aromatic rings such as benzene are also unaffected (<span style=\"color: #993366;\"><em>the unusually low reactivity of benzene is covered in a subsequent chapter &#8211; see <a href=\"https:\/\/www.masterorganicchemistry.com\/2017\/01\/20\/introduction-aromaticity\/\">Introduction to Aromaticity<\/a><\/em><\/span>).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35848\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/12\/4-lindlars-catalyst-only-reduces-alkynes-does-not-react-with-alkenes-or-aromatic-rings-1.gif\" alt=\"-lindlars catalyst only reduces alkynes - does not react with alkenes or aromatic rings\" width=\"640\" height=\"472\" \/><\/a><\/p>\n<p>Deuterium, the heavy isotope of hydrogen, can be used in place of hydrogen gas.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-35849\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/12\/5-deuterium-can-be-used-in-partial-hydrogenation-of-alkynes-to-incorporate-D-into-alkenes-1-1.gif\" alt=\"deuterium can be used in partial hydrogenation of alkynes to incorporate D into alkenes\" width=\"640\" height=\"247\" \/><\/a><\/p>\n<h2><a id=\"three\"><\/a>3. Applications of Lindlar&#8217;s Catalyst<\/h2>\n<p>As mentioned above, a key feature of partial hydrogenation of alkynes is that it unlocks all the reactions of alkenes.<\/p>\n<p>For example, alkynes don&#8217;t undergo epoxidation with\u00a0<em>m-<\/em>CPBA or dihydroxylation with OsO<sub>4<\/sub>. But alkenes do!<\/p>\n<p>See if you can draw the product that is formed when an alkyne is partially hydrogenated with Lindlar&#8217;s catalyst and then treated with OsO<sub>4<\/sub>.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35829\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35829\"] {\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=\"35829\"] {\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=\"35829\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35829\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35829 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35829\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-2x8h1\" data-id=\"2x8h1\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2640-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2640-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>In these types of quiz questions, it&#8217;s very important to pay close attention to the <strong>stereoselective\u00a0<\/strong>nature of the Lindlar reduction.<\/p>\n<p>Lindlar&#8217;s catalyst is notable in that it makes\u00a0<em>cis<\/em>-alkenes from alkynes. Another reagent, sodium in ammonia (Na\/NH<sub>3<\/sub>) can reduce alkynes to\u00a0<em>trans-<\/em>alkenes. (<span style=\"color: #993366;\"><em>See article &#8211; <a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/05\/08\/lindlar-nanh3-partial-reduction-of-alkynes\/\">Reduction of Alkynes to trans-Alkenes With Na\/NH<sub>3<\/sub><\/a><\/em><\/span>).<\/p>\n<p>Keeping stereochemistry straight is extremely important both in the\u00a0<strong>forward\u00a0<\/strong>(i.e. predicting the products) and\u00a0<strong>reverse\u00a0<\/strong>directions (e.g. synthesis problems, see below).<\/p>\n<p>Try this example with\u00a0<strong>halogenation<\/strong>.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"45640\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"45640\"] {\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=\"45640\"] {\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=\"45640\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-45640\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-45640 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"45640\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-ps9p9\" data-id=\"ps9p9\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2641-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2641-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>Here is an example incorporating the addition of HBr :<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35831\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35831\"] {\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=\"35831\"] {\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=\"35831\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35831\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35831 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35831\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-w9cem\" data-id=\"w9cem\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2642-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2642-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p><span style=\"color: #993366;\"><em>Yes &#8211; even though we&#8217;re in the chapter on alkynes, Markovnikov&#8217;s rule still applies :-) .<\/em><\/span><\/p>\n<p>Finally, an epoxidation example:<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35832\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35832\"] {\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=\"35832\"] {\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=\"35832\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35832\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35832 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35832\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-befp9\" data-id=\"befp9\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2643-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2643-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<h2><a id=\"four\"><\/a>4. Synthesis Questions With Lindlar&#8217;s Catalyst<\/h2>\n<p>Now that we have a reaction for building up the carbon chain (acetylide alkylation) and a reaction for converting alkynes to alkenes (partial hydrogenation) a whole world is opening up before us.<\/p>\n<p>We can finally think about how we would carry out the <strong>synthesis<\/strong> of larger molecules from <strong>smaller <\/strong>molecules through a series of well-planned reactions.<\/p>\n<p><span style=\"color: #993366;\"><em>It&#8217;s like putting together Lego bricks, but instead of pushing Lego nubs into the holes of another brick, we&#8217;ll be adding <strong>nucleophiles\u00a0<\/strong>to\u00a0<strong>electrophiles<\/strong>.\u00a0<\/em><\/span><\/p>\n<p>Here&#8217;s a typical example. How would you synthesize this <strong>diol<\/strong> from the alkyne (below left) using any inorganic reagents and carbon fragments with two carbons or less?<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35810\"><style type=\"text\/css\" id=\"wq-personality-custom-css\">.wq-quiz-wrapper[data-id=\"35810\"] {\n--wq-question-width: 100%;\n--wq-question-color: #009cff;\n--wq-question-height: auto;\n--wq-bar-color: #00c479;\n--wq-font-color: #444;\n--wq-background-color: #f2f2f2;\n}\n<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35810\" class=\"wq_quizCtr multiple personality_quiz wq-quiz wq-quiz-35810 wq-quiz-personality wq-layout-multiple wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35810\">\n<!-- Progress bar -->\n<div class=\"wq-progress-bar-container wq_quizProgressBarCtr\">\n\t<div class=\"wq_quizProgressBar\">\n\t\t<span class=\"wq_quizProgressValue\" style=\"width: 0%;\">0%<\/span>\n\t<\/div>\n<\/div>\n<!-- \/\/ Progress bar-->\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-41bqw\" data-index=\"0\">\n\n\t\n\t<div class=\"wq_singleQuestionCtr\">\n\t\t<div class=\"wq_questionTextWrapper quiz-pro-clearfix\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\n\t\t<div class=\"wq_questionMediaCtr\">\n\t\t\t<div class=\"wq_questionImage wq-question-image\">\n\t\t\t<img loading=\"lazy\" decoding=\"async\" width=\"898\" height=\"486\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/12\/2644-1-Synthesis.gif\" class=\"attachment-full size-full\" alt=\"\" \/>\t\n\t<\/div>\n\t\t<\/div>\n\n\t\t<div class=\"wq-question-answers wq_questionAnswersCtr\">\n\t\t\t<div class=\"wq-answers wq_answersWrapper\">\n\t\t\t<div class=\"wq-answer wq_singleAnswerCtr wq_hasImage\" data-id=\"y10ax\">\n\t\t\t<label class=\"wq_answerTxtCtr\">2-What's Different<\/label>\n\t\t<\/div>\n\t<\/div>\n\t\t<\/div>\n\n\t\t\n\t\t<div class=\"wq-personality-question-explanation wq_personalityQuestionExplanation\">\n\t\t\t<div class=\"wq-explanation-head wq_ExplanationHead\"><\/div>\n\t\t\t<p class=\"wq-explanation-text wq_QuestionExplanationText\">What's different? What bonds have formed and broken?<\/p>\n\t\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<div class=\"wq-question wq_singleQuestionWrapper wq-question-epmsp\" data-index=\"1\">\n\n\t\n\t<div class=\"wq_singleQuestionCtr\">\n\t\t<div class=\"wq_questionTextWrapper quiz-pro-clearfix\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4> <\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\n\t\t<div class=\"wq_questionMediaCtr\">\n\t\t\t<div class=\"wq_questionImage wq-question-image\">\n\t\t\t<img loading=\"lazy\" decoding=\"async\" width=\"898\" height=\"634\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/12\/2644-2-Synthesis.gif\" class=\"attachment-full size-full\" alt=\"\" \/>\t\n\t<\/div>\n\t\t<\/div>\n\n\t\t<div class=\"wq-question-answers wq_questionAnswersCtr\">\n\t\t\t<div class=\"wq-answers wq_answersWrapper\">\n\t<div class=\"row\">\n\t\t\n\t\t\t<div class=\"col-md-wq-4\">\n\t\t\t\t<div class=\"wq-answer wq_singleAnswerCtr wq_hasImage\" data-id=\"6h6j3\">\n\n\t\t\t\t\t\t\t\t\t\t\t<div class=\"wq_answerImgCtr\">\n\t\t\t\t\t\t\t<img loading=\"lazy\" decoding=\"async\" width=\"884\" height=\"780\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/12\/2644-3-Synthesis.gif\" class=\"attachment-full size-full\" alt=\"\" \/>\t\t\t\t\t\t<\/div>\n\t\t\t\t\t\n\t\t\t\t\t\t\t\t\t\t\t<label class=\"wq_answerTxtCtr\">What Reactions?<\/label>\n\t\t\t\t\t\t\t\t\t<\/div>\n\t\t\t<\/div>\n\n\t\t\t\n\t\t\t<\/div>\n<\/div>\n\t\t<\/div>\n\n\t\t\n\t\t<div class=\"wq-personality-question-explanation wq_personalityQuestionExplanation\">\n\t\t\t<div class=\"wq-explanation-head wq_ExplanationHead\"><\/div>\n\t\t\t<p class=\"wq-explanation-text wq_QuestionExplanationText\"><\/p>\n\t\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<div class=\"wq-question wq_singleQuestionWrapper wq-question-q50wb\" data-index=\"2\">\n\n\t\n\t<div class=\"wq_singleQuestionCtr\">\n\t\t<div class=\"wq_questionTextWrapper quiz-pro-clearfix\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\n\t\t<div class=\"wq_questionMediaCtr\">\n\t\t\t<div class=\"wq_questionImage wq-question-image\">\n\t\t\t<img loading=\"lazy\" decoding=\"async\" width=\"884\" height=\"780\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/12\/2644-3-Synthesis.gif\" class=\"attachment-full size-full\" alt=\"\" \/>\t\n\t<\/div>\n\t\t<\/div>\n\n\t\t<div class=\"wq-question-answers wq_questionAnswersCtr\">\n\t\t\t<div class=\"wq-answers wq_answersWrapper\">\n\t\t\t<div class=\"wq-answer wq_singleAnswerCtr wq_hasImage\" data-id=\"cgxfy\">\n\t\t\t<label class=\"wq_answerTxtCtr\">In What Order?<\/label>\n\t\t<\/div>\n\t<\/div>\n\t\t<\/div>\n\n\t\t\n\t\t<div class=\"wq-personality-question-explanation wq_personalityQuestionExplanation\">\n\t\t\t<div class=\"wq-explanation-head wq_ExplanationHead\"><\/div>\n\t\t\t<p class=\"wq-explanation-text wq_QuestionExplanationText\"><\/p>\n\t\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<div class=\"wq-question wq_singleQuestionWrapper wq-question-vssgs\" data-index=\"3\">\n\n\t\n\t<div class=\"wq_singleQuestionCtr\">\n\t\t<div class=\"wq_questionTextWrapper quiz-pro-clearfix\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\n\t\t<div class=\"wq_questionMediaCtr\">\n\t\t\t<div class=\"wq_questionImage wq-question-image\">\n\t\t\t<img loading=\"lazy\" decoding=\"async\" width=\"898\" height=\"984\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/12\/2644-4-Synthesis.gif\" class=\"attachment-full size-full\" alt=\"\" \/>\t\n\t<\/div>\n\t\t<\/div>\n\n\t\t<div class=\"wq-question-answers wq_questionAnswersCtr\">\n\t\t\t<div class=\"wq-answers wq_answersWrapper\">\n\t\t\t<div class=\"wq-answer wq_singleAnswerCtr wq_hasImage\" data-id=\"mufk7\">\n\t\t\t<label class=\"wq_answerTxtCtr\">Final Sequence<\/label>\n\t\t<\/div>\n\t<\/div>\n\t\t<\/div>\n\n\t\t\n\t\t<div class=\"wq-personality-question-explanation wq_personalityQuestionExplanation\">\n\t\t\t<div class=\"wq-explanation-head wq_ExplanationHead\"><\/div>\n\t\t\t<p class=\"wq-explanation-text wq_QuestionExplanationText\"><\/p>\n\t\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<div class=\"wq-results wq_resultsCtr\">\n\t<span class=\"wq-result-quiz-title wq_quizTitle\">Quiz 2644-Synthesis<\/span>\n<div class=\"wq-result wq_singleResultWrapper\" data-id=\"zpkbf\">\n\n\t<div class=\"wq-result-score wq_resultScoreCtr\"><\/div>\n\n\t<div class=\"wq-result-title wq_resultTitle\"><\/div>\n\n\t\t\t<p><img loading=\"lazy\" decoding=\"async\" width=\"898\" height=\"810\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/2023\/12\/2644-5-Synthesis.gif\" class=\"wq-result-img wq_resultImg\" alt=\"\" \/><\/p>\n\t\n\t<div class=\"wq_resultDesc\"><\/div>\n<\/div>\n<\/div><!-- End .wq-results -->\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>Working on these types of problems takes some practice. I&#8217;ll have more to say about it elsewhere, but when working on these problems, I advise breaking it down to the following exercises:<\/p>\n<ol>\n<li>Examine\u00a0<strong>what&#8217;s new\u00a0<\/strong>&#8211; what <strong>specific<\/strong> bonds have formed (and broken) in going from the starting material to the product? <em>This is your to-do list<\/em>.<\/li>\n<li>What\u00a0<strong>reactions<\/strong> do you know that form and break those bonds?<\/li>\n<li>In what\u00a0<strong>order\u00a0<\/strong>do we need to do these reactions?<\/li>\n<\/ol>\n<p>Once you&#8217;ve answered these questions, you can start thinking about how you would carry out the sequence in a forward direction.<\/p>\n<p>One\u00a0<strong>key<\/strong> factor not to be forgotten is the importance of\u00a0<strong>stereochemistry<\/strong>.<\/p>\n<p>When planning out these reactions, it&#8217;s not enough to know that, say, Lindlar&#8217;s catalyst does the partial reduction of an alkyne to an alkene. It&#8217;s\u00a0<strong>crucial\u00a0<\/strong>to also include that the reduction occurs in a\u00a0<strong>cis<\/strong> fashion. If you leave out that detail, you won&#8217;t get full credit for your answers.<\/p>\n<p>Here&#8217;s another example of a synthesis problem involving\u00a0epoxidation (<em>m-<\/em>CPBA).<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35833\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35833\"] {\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=\"35833\"] {\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=\"35833\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35833\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35833 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35833\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-yb35b\" data-id=\"yb35b\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2645-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2645-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>Here&#8217;s another example of a synthesis question that involves chlorination (remember that this is selective for the\u00a0<em>anti<\/em>-addition product.<\/p>\n<div class=\"wq-quiz-wrapper\" data-id=\"35834\"><style type=\"text\/css\" id=\"wq-flip-custom-css\">.wq-quiz-wrapper[data-id=\"35834\"] {\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=\"35834\"] {\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=\"35834\"] .wq_singleQuestionWrapper { width:100% !important; height:auto !important; }\n\t\t\t}\n\t\t<\/style><!-- wp quiz -->\n<div id=\"wp-quiz-35834\" class=\"wq_quizCtr single flip_quiz wq-quiz wq-quiz-35834 wq-quiz-flip wq-layout-single wq-skin-traditional wq-should-show-correct-answer\" data-quiz-id=\"35834\">\n<div class=\"wq-questions wq_questionsCtr\">\n\t<div class=\"wq-question wq_singleQuestionWrapper wq-question-1mhv1\" data-id=\"1mhv1\">\n\n\t\n\t<div class=\"item_top\">\n\t\t<div class=\"title_container\">\n\t\t\t<div class=\"wq_questionTextCtr\">\n\t\t\t\t<h4 class=\"wq-question-title\"><\/h4>\n\t\t\t<\/div>\n\t\t<\/div>\n\t<\/div>\n\n\t<div class=\"card \">\n\t\t<div class=\"front\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2646-Front.gif\" \/>\n\t\t\n\t\t\n\t\n\t\n\t\t\t<span class=\"top-desc\">Click to Flip<\/span>\n\t<\/div>\n\t\t<div class=\"back\" >\n\t\n\t\t\t\t\t<img decoding=\"async\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-images\/2646-Reverse.gif\" \/>\n\t\t\n\t\t\n\t\n\t<\/div>\n\t<\/div>\n\n\t\n<\/div>\n<\/div>\n<\/div>\n<!-- \/\/ wp quiz-->\n<\/div><!-- End .wq-quiz-wrapper -->\n<p>In this example, we had a vicinal dihalide that was drawn in a conformation where both C-Cl bonds were wedges. If we worked backwards from this without accounting for the stereochemistry, we&#8217;d end up with the wrong double-bond geometry.<\/p>\n<h2><a id=\"five\"><\/a>5. Summary<\/h2>\n<p>Lindlar&#8217;s catalyst is used for the partial reduction of alkynes to\u00a0<em>cis<\/em>-alkenes. Be on the lookout for synthesis questions involving Lindlar&#8217;s catalyst and pay close attention to stereochemistry.<\/p>\n<p>In the next article we will cover a reaction for the partial reduction of alkynes to give\u00a0<em>trans<\/em> alkenes, Na\/NH<sub>3<\/sub> (sodium in ammonia).<\/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\/2011\/11\/25\/palladium-on-carbon-pdc\/\" class=\"\"><span>Palladium on Carbon (Pd\/C) for Catalytic Hydrogenation<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/05\/08\/lindlar-nanh3-partial-reduction-of-alkynes\/\" class=\"\"><span>Partial Reduction of Alkynes With Lindlar\u2019s Catalyst or Na\/NH3 To Obtain Cis or Trans Alkenes<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2024\/01\/23\/alkyne-hydroboration-with-r2bh\/\" class=\"\"><span>Alkyne Hydroboration With \u201cR2BH\u201d<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/07\/25\/calculating-the-oxidation-state-of-a-carbon\/\" class=\"\"><span>Calculating the oxidation state of a carbon<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/07\/01\/reagent-friday-oso4-osmium-tetroxide\/\" class=\"\"><span>OsO4 (Osmium Tetroxide) for Dihydroxylation of Alkenes<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2011\/06\/17\/reagent-friday-m-cpba-meta-chloroperoxybenzoic-acid\/\" class=\"\"><span>m-CPBA (meta-chloroperoxybenzoic acid)<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2014\/01\/21\/synthesis-reactions-of-alkenes\/\" class=\"\"><span>Synthesis (4) \u2013 Alkene Reaction Map, Including Alkyl Halide Reactions<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/05\/01\/the-2-most-important-reactions-of-alkynes\/\" class=\"\"><span>Acetylides from Alkynes, And Substitution Reactions of Acetylides<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/03\/15\/alkene-bromination-mechanism\/\" class=\"\"><span>Halogenation of Alkenes and Halohydrin Formation<\/span><\/a><\/li><li><a href=\"https:\/\/www.masterorganicchemistry.com\/2013\/02\/08\/markovnikovs-rule-1\/\" class=\"\"><span>Hydrohalogenation of Alkenes and Markovnikov\u2019s Rule<\/span><\/a><\/li><\/ul><\/div>\n<p><strong><a id=\"noteone\"><\/a>Note 1.\u00a0<\/strong>One of the outstanding challenges in modern organic chemistry &#8211; a &#8220;<a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/ar00051a009\">holy grail<\/a>&#8220;, if you will &#8211;\u00a0 is actually how to take a relatively unreactive functional group like an alkane C-H bond and transform it to a more reactive functional group such as C-OH or C-Cl with high selectivity. This extremely active area of research is known as &#8220;<a href=\"https:\/\/www.chemistryworld.com\/holy-grails\/the-grails\/c-h-bond-activation\">C-H activation<\/a>&#8220;.<\/p>\n<p><strong><a id=\"notetwo\"><\/a>Note 2. <\/strong>Technically, Lindlar&#8217;s catalyst is Pd on calcium carbonate that has been treated with a trace amount of lead salt (the procedure is <a href=\"http:\/\/www.orgsyn.org\/demo.aspx?prep=CV5P0880\"><strong>here<\/strong><\/a>). It has been found that addition of small amounts of\u00a0<strong>quinoline\u00a0<\/strong>also helps with selectivity (so do certain thiols).<\/p>\n<p><strong><a id=\"notethree\"><\/a>Note 3. <\/strong>Nickel boride is made through the reduction of Ni(II) acetate with sodium borohydride (NaBH<sub>4<\/sub>) in methanol. It is a hydrogenation catalyst. A representative procedure can be found <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo00952a024\">here<\/a>.<\/p>\n<hr \/>\n<h2><strong><a id=\"quiz\"><\/a>Quiz Yourself!<\/strong><\/h2>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0695-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0723-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/0727-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/2654-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n\n<p class=\"p1\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone wp-image-26714\" src=\"https:\/\/www.masterorganicchemistry.com\/wp-content\/uploads\/quiz-previews\/2647-Front-Image-Only.png\" alt=\"\" width=\"640\" height=\"616\" \/><\/p>\n<p><a href=\"https:\/\/www.masterorganicchemistry.com\/moc-membership\/\"><strong>Become a\u00a0 MOC member<\/strong><\/a> to see the clickable quiz with answers on the back. <\/p>\n<hr \/>\n<h2><strong><a id=\"references\"><\/a>(Advanced) References and Further Reading<\/strong><\/h2>\n<ol>\n<li><strong>Catalytic Semihydrogenation of the Triple Bond<\/strong><br \/>\nElliot N. MARVELL*, Thomas LI<br \/>\n<em>Synthesis\u00a0<\/em><strong>1973<\/strong>, 457-468<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/www.sciencedirect.com\/science\/article\/abs\/pii\/0040402061800501\">10.1055\/s-1973-22234<\/a><br \/>\nFairly comprehensive review, still relevant today, on various methods for partial hydrogenation of alkynes.<\/li>\n<li><strong>Ein neuer Katalysator f\u00fcr selektive Hydrierungen<\/strong><br \/>\nH. Lindlar<br \/>\n<em>Helv<\/em>. <em> Chim. Acta <\/em><strong>1952\u00a0<\/strong><em>35\u00a0<\/em>(2), 446<br \/>\n<strong>DOI:<\/strong> <a href=\"https:\/\/onlinelibrary.wiley.com\/doi\/abs\/10.1002\/hlca.19520350205\">10.1002\/hlca.19520350205<\/a><br \/>\nThe original paper by Lindlar describing the development of a new catalyst for the selective hydrogenation of alkynes to Z-alkenes during Vitamin A synthesis.<\/li>\n<li><strong><a id=\"refthree\"><\/a>PALLADIUM CATALYST FOR PARTIAL REDUCTION OF ACETYLENES<br \/>\n<\/strong>H. Lindlar, R. Dubuis<br \/>\n<em>Org. Synth. <\/em><strong>1966<\/strong>, <em>46<\/em>, 89<br \/>\n<strong>DOI: <\/strong><a href=\"http:\/\/www.orgsyn.org\/demo.aspx?prep=CV5P0880\">10.15227\/orgsyn.046.0089<\/a><br \/>\nThis procedure by Lindlar also gives a detailed preparation of the catalyst.<\/li>\n<li><strong><a id=\"reffour\"><\/a>A density functional theory study of the \u2018mythic\u2019 Lindlar hydrogenation catalyst<br \/>\n<\/strong> Garc\u0131\u00b4a-Mota, J. Gomez-D\u0131\u00b4az, G. Novell-Leruth, C. Vargas-Fuentes, L. Bellarosa, B. Bridier, J. Pe\u00b4rez-Ram\u0131\u00b4rez, N. Lo\u00b4pez<br \/>\n<em>Theor. Chem. Acc.\u00a0<\/em><strong>2011, <\/strong><em>128<\/em>, 663<br \/>\n<strong>DOI:\u00a0<\/strong><a href=\"https:\/\/link.springer.com\/article\/10.1007\/s00214-010-0800-0\">10.1021\/s00214-010-0800-0<\/a><br \/>\nThis is a computational investigation using DFT (density functional theory) which studies how the various components in the Lindlar catalyst (Pd, Pb, quinoline) pack together and how that contributes to hydrogenation selectivity.<\/li>\n<li><strong>(Z)-4-(TRIMETHYLSILYL)-3-BUTEN-1-OL<br \/>\n<\/strong>L.E. Overman, M. J. Brown, S. F. McCann <a href=\"http:\/\/www.orgsyn.org\/Result.aspx\"><br \/>\n<\/a><em>Org. Synth.\u00a0<\/em><strong>1990,\u00a0<\/strong><em>68<\/em>, 182<br \/>\n<strong>DOI: <\/strong><a href=\"http:\/\/www.orgsyn.org\/Result.aspx\">10.15227\/orgsyn.068.0182<\/a><br \/>\nThe second reaction in this 2-step synthesis is a Lindlar hydrogenation to give the Z-alkene.<\/li>\n<li><strong>SYNTHETICALLY USEFUL REACTIONS WITH NICKEL BORIDE. A REVIEW<br \/>\n<\/strong>Jitender M. Khurana, Amita Gogia.<br \/>\n<em>Organic Preparations and Procedures International The New Journal for Organic Synthesis <\/em><br \/>\n<strong>DOI: <\/strong><a href=\"https:\/\/www.tandfonline.com\/doi\/abs\/10.1080\/00304949709355171\">1080\/00304949709355171<\/a><br \/>\nThis is a review on the application of nickel boride in organic synthesis, which can be used in similar applications to Lindlar\u2019s catalyst.<\/li>\n<li><strong>Selective catalytic hydrogenation of acetylenes,<\/strong><br \/>\nN.A. Dobson, G. Eglinton, M. Krishnamurti, R.A. Raphael, R.G. Willis,<br \/>\n<em>Tetrahedron,\u00a0<\/em><strong>1961,<\/strong>16<em>, 16-24<br \/>\n<\/em><strong>DOI<\/strong><em><strong>: <\/strong><\/em><a href=\"https:\/\/doi.org\/10.1016\/0040-4020(61)80050-1\">10.1016\/0040-4020(61)80050-1<\/a><br \/>\nIn this article the authors establish that terminal alkynes are more reactive towards hydrogenation than internal alkynes, and internal alkynes are more reactive towards hydrogenation than alkenes. They also demonstrate that alkynes can be selectively hydrogenated by limiting the number of equivalents of hydrogen to one equivalent.<\/li>\n<li><strong>Catalytic hydrogenation. VI. Reaction of sodium borohydride with nickel salts in ethanol solution. P-2 Nickel, a highly convenient, new, selective hydrogenation catalyst with great sensitivity to substrate structure<\/strong><br \/>\nCharles Allan Brown and Vijay K. Ahuja<br \/>\n<em>The Journal of Organic Chemistry<\/em> <strong>1973<\/strong> 38 (12), 2226-2230<br \/>\n<strong>DOI<\/strong>: <a href=\"https:\/\/pubs.acs.org\/doi\/10.1021\/jo00952a024\">10.1021\/jo00952a024<\/a><br \/>\nThis work introduces P-2 nickel boride for the reduction of alkynes to <em>cis-<\/em>alkenes.<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"<p>Partial Reduction of Alkynes to cis Alkenes with the Lindlar Catalyst Alkynes are generally more reactive towards catalytic hydrogenation (e.g. Pd-C, H2) than alkenes\u00a0 While <\/p>\n","protected":false},"author":1,"featured_media":35853,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[1419],"tags":[477,529,527,292,524,525,412,526,274,352],"post_folder":[],"class_list":["post-1944","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-alkyne-reactions","tag-alkynes-2","tag-catalyst","tag-cis","tag-hydrogenation","tag-lindlar","tag-partial-reduction","tag-reagent-friday","tag-reducing-agent","tag-stereoselective","tag-synthesis"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.7 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Lindlar&#039;s Catalyst as a Reagent in Organic Chemistry<\/title>\n<meta name=\"description\" content=\"Lindlar&#039;s catalyst is a &quot;poisoned&quot; metal catalyst that performs hydrogenations of alkynes in the presence of hydrogen gas 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