{"id":1924,"date":"2018-11-30T15:59:41","date_gmt":"2018-11-30T15:59:41","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/?post_type=chapter&#038;p=1924"},"modified":"2019-01-09T09:20:46","modified_gmt":"2019-01-09T09:20:46","slug":"simple-mechanism-with-strong-nucleophiles","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/simple-mechanism-with-strong-nucleophiles\/","title":{"raw":"22.2. Simple mechanism with strong nucleophiles","rendered":"22.2. Simple mechanism with strong nucleophiles"},"content":{"raw":"<header>\r\n<div>\r\n<h2>Transesterification<\/h2>\r\n<\/div>\r\n<\/header><article id=\"elm-main-content\" class=\"elm-content-container\"><section class=\"mt-content-container\">Transesterification is the conversion of a carboxylic acid ester into a different carboxylic acid ester.\r\n<div id=\"section_1\" class=\"mt-section\">\r\n<h3 class=\"editable\">Introduction<\/h3>\r\nWhen in ester is placed in a large excess of an alcohol along with presence of either an acid or a base there can be an exchange of alkoxy groups. The large excess of alcohol is used to drive the reaction forward. The most common method of transesterification is the reaction of the ester with an alcohol in the presence of an acid catalyst e.g.:\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153544\/transesterification1.png\" alt=\"\" width=\"644\" height=\"77\" \/>\r\n\r\nThis reaction has the following mechanism:\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153547\/transesterification2.png\" alt=\"\" width=\"626\" height=\"595\" \/>\r\n\r\nSince both the reactants and the products are an ester and an alcohol, the reaction is reversible and the equilibrium constant is close to one. \u00a0Consequently, the <a title=\"Le Ch\u00e2telier's Principle\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Physical_and_Theoretical_Chemistry_Textbook_Maps\/Supplemental_Modules_(Physical_and_Theoretical_Chemistry)\/Equilibria\/Le_Chatelier's_Principle\" rel=\"internal\">Le Chatelier\u2019s principle<\/a> has to be exploited to drive the reaction to completion. The simplest way to do so is to use the alcohol as the solvent as well.\r\n<div id=\"section_2\" class=\"mt-section\">\r\n<h4 class=\"editable\">General reaction<\/h4>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153550\/1.jpg\" alt=\"1.jpg\" \/><img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153552\/2.jpg\" alt=\"2.jpg\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_3\" class=\"mt-section\">\r\n<h3 class=\"editable\">Mechanism in basic conditions<\/h3>\r\nNucleophilic attack by an alkoxide\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153554\/3.jpg\" alt=\"3.jpg\" \/>\r\n\r\n2) Leaving group removal\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153556\/4.jpg\" alt=\"4.jpg\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_4\" class=\"mt-section\"><\/div>\r\n<div id=\"section_5\" class=\"mt-section\">\r\n<h3 class=\"editable\">Contributors<\/h3>\r\nProf. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)\r\n<ul>\r\n \t<li><a class=\"external\" title=\"http:\/\/www.uvu.edu\/profpages\/profiles\/show\/user_id\/1776\" href=\"http:\/\/www.uvu.edu\/profpages\/profiles\/show\/user_id\/1776\" target=\"_blank\" rel=\"external nofollow noopener\"><span class=\"gD\">Gamini Gunawardena<\/span><\/a> from the <a class=\"external\" title=\"http:\/\/science.uvu.edu\/ochem\/\" href=\"http:\/\/science.uvu.edu\/ochem\/\" target=\"_blank\" rel=\"external nofollow noopener\">OChemPal <\/a>site (<a class=\"external\" title=\"http:\/\/www.uvu.edu\/chemistry\/\" href=\"http:\/\/www.uvu.edu\/chemistry\/\" target=\"_blank\" rel=\"external nofollow noopener\">Utah Valley University<\/a>)<\/li>\r\n<\/ul>\r\n<header>\r\n<h2 id=\"title\">Saponification<\/h2>\r\n<dl class=\"mt-last-updated-container\"><\/dl>\r\n<\/header><section class=\"mt-content-container\"><a title=\"Esters\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Esters\" rel=\"internal\">Esters <\/a>can be cleaved back into a carboxylic acid and an alcohol by reaction with water and a base. The reaction is called a saponification from the Latin <em>sapo <\/em>which means soap. The name comes from the fact that soap used to me made by the ester hydrolysis of fats. Due to the basic conditions a carboxylate ion is made rather than a <a title=\"Carboxylic Acids\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Carboxylic_Acids\" rel=\"internal\">carboxylic acid.<\/a>\r\n<div id=\"section_1\" class=\"mt-section\">\r\n<h3 class=\"editable\">General reaction<\/h3>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153742\/1.jpg\" alt=\"1.jpg\" \/>\r\n<div class=\"textbox examples\">\r\n<h3>Example<\/h3>\r\n<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153744\/2.jpg\" alt=\"2.jpg\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_2\" class=\"mt-section\">\r\n<h3 class=\"editable\">Mechanism<\/h3>\r\n1)\u00a0 Nucleophilic attack by hydroxide\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153747\/3.jpg\" alt=\"3.jpg\" width=\"371\" height=\"177\" \/>\r\n\r\n2) Leaving group removal\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153749\/4a.jpg\" alt=\"4a.jpg\" width=\"510\" height=\"137\" \/>\r\n\r\n3)\u00a0 Deprotonation\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153751\/5.jpg\" alt=\"5.jpg\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_3\" class=\"mt-section\">\r\n<h3 class=\"editable\">Contributors<\/h3>\r\nProf. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)\r\n<h2>Alkaline hydrolysis of amides<\/h2>\r\nIn alkaline hydrolysis the amide is heated with boiling aqueous sodium or potassium hydroxide. The nucleophilic hydroxide ion adds to the carbonyl carbon to form a tetrahedral intermediate, which, with the help of the aqueous solvent, expels the nitrogen as the free amine:\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30160907\/Roberts_and_Caserio_Screenshot_24-4-3.jpg\" alt=\"\" width=\"491px\" height=\"112px\" \/>\r\n\r\n<section class=\"mt-content-container\">\r\n<div class=\"mt-section\"><header>\r\n<h2 id=\"title\">Reduction of carboxylic acids and their derivatives<\/h2>\r\n<\/header><section class=\"mt-content-container\">\r\n<div id=\"section_1\" class=\"mt-section\">\r\n<h3 class=\"editable\">Reduction of acid chlorides and esters<\/h3>\r\nAcid (acyl) chlorides can be converted to\u00a0aldehydes using lithium tri-tert-butoxyaluminium hydride (LiAlH(Ot-Bu)<sub>3<\/sub>). The hydride source (LiAlH(Ot-Bu)<sub>3<\/sub>) is a weaker reducing agent than lithium aluminum hydride. Because acid chlorides are highly activated they\u00a0still react with the hydride source;\u00a0however, the formed aldehyde will react slowly, which allows for its isolation.\r\n\r\nGeneral reaction:\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154120\/1.jpg\" alt=\"1.jpg\" width=\"392px\" height=\"135px\" \/>\r\n<div class=\"textbox examples\">\r\n<h3>Example<\/h3>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154122\/2.jpg\" alt=\"2.jpg\" width=\"459px\" height=\"119px\" \/>\r\n\r\n<\/div>\r\n<span style=\"font-size: 1rem;text-align: initial\">Acid chlorides can be converted to\u00a0aldehydes using lithium tri-tert-butoxyaluminium hydride (LiAlH(Ot-Bu)<\/span><sub style=\"text-align: initial\">3<\/sub><span style=\"font-size: 1rem;text-align: initial\">). The hydride source (LiAlH(Ot-Bu)<\/span><sub style=\"text-align: initial\">3<\/sub><span style=\"font-size: 1rem;text-align: initial\">) is a weaker reducing agent than lithium aluminum hydride. Because acid chlorides are highly activated they\u00a0still react with the hydride source;\u00a0however, the formed aldehyde will react slowly, which allows for its isolation.<\/span>\r\n\r\nGeneral Reaction:\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154120\/1.jpg\" alt=\"1.jpg\" width=\"392px\" height=\"135px\" \/>\r\n<div class=\"textbox examples\">\r\n<h3>Example<\/h3>\r\n<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154122\/2.jpg\" alt=\"2.jpg\" width=\"459px\" height=\"119px\" \/>\r\n\r\n<\/div>\r\n&nbsp;\r\n\r\nEsters can be converted to aldehydes using diisobutylaluminium hydride (DIBAH). \u00a0The reaction is usually carried out at -78 <sup>o<\/sup>C to prevent reaction with the aldehyde product.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154125\/1.jpg\" alt=\"1.jpg\" \/>\r\n<div class=\"textbox examples\">\r\n<h3>Example<\/h3>\r\n<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154127\/2.jpg\" alt=\"2.jpg\" \/>\r\n\r\n<\/div>\r\n&nbsp;\r\n\r\nEsters can be converted to 1<sup>o<\/sup> alcohols using LiAlH<sub>4<\/sub>, while sodium borohydride ($$NaBH_4$$) is not a strong enough reducing agent to perform this reaction.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154129\/1.jpg\" alt=\"1.jpg\" width=\"475\" height=\"113\" \/>\r\n<div class=\"textbox examples\">\r\n<h3>Example<\/h3>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154132\/2.jpg\" alt=\"2.jpg\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_2\" class=\"mt-section\">\r\n<h3 class=\"editable\">Mechanism<\/h3>\r\n1) Nucleophilic attack by the hydride\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154135\/3.jpg\" alt=\"3.jpg\" \/>\r\n\r\n2) Leaving group removal\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154139\/4.jpg\" alt=\"4.jpg\" width=\"515\" height=\"142\" \/>\r\n\r\n3) Nucleophilic attack by the hydride anion\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154142\/5.jpg\" alt=\"5.jpg\" width=\"463\" height=\"204\" \/>\r\n\r\n4) The alkoxide is protonated\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154144\/6.jpg\" alt=\"6.jpg\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_4\" class=\"mt-section\">\r\n<h3 class=\"editable\"><strong>Going from reactant to products simplified<\/strong><\/h3>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154149\/2.jpg\" alt=\"2.jpg\" width=\"644px\" height=\"71px\" \/>\r\n<div class=\"textbox examples\">\r\n<h3>Example<\/h3>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154151\/3.jpg\" alt=\"3.jpg\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_6\" class=\"mt-section\">\r\n<h3><\/h3>\r\n<h2 class=\"editable\">Reduction of amides using LiAlH<sub>4<\/sub>.<\/h2>\r\n<\/div>\r\n<div id=\"section_7\" class=\"mt-section\">\r\n<h3 class=\"editable\">General Reaction<\/h3>\r\n<p style=\"text-align: center\"><img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154225\/1.jpg\" alt=\"1.jpg\" \/><\/p>\r\n\r\n<div class=\"textbox examples\">\r\n<h3>Example: Amide Reduction<\/h3>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154227\/2.jpg\" alt=\"2.jpg\" \/>\r\n\r\nAlkyl groups attached to the nitrogen do not affect the reaction.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154229\/3.jpg\" alt=\"3.jpg\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_8\" class=\"mt-section\">\r\n\r\n&nbsp;\r\n<h3 class=\"editable\">Mechanism<\/h3>\r\n1) Nucleophilic attack by the hydride\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154231\/4.jpg\" alt=\"4.jpg\" \/>\r\n\r\n2) Leaving group removal\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154234\/5.jpg\" alt=\"5.jpg\" \/>\r\n\r\n3) Nucleophilic attack by the hydride\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154236\/6.jpg\" alt=\"6.jpg\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_9\" class=\"mt-section\">\r\n<h3 class=\"editable\">Contributors<\/h3>\r\n<ul>\r\n \t<li>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/li>\r\n<\/ul>\r\n<header><\/header><section class=\"mt-content-container\">\r\n<div id=\"section_3\" class=\"mt-section\"><section class=\"mt-content-container\">\r\n<div id=\"s66923\" class=\"mt-include\">\r\n<div id=\"section_2\" class=\"mt-section\">\r\n<h3><\/h3>\r\n<h2 id=\"REACTIONS_WITH_ACID_CHLORIDES_AND_ESTERS-66923\">Reduction of acid chlorides and esters using LiAlH<sub>4<\/sub><\/h2>\r\nThe mechanism of action of hydride reductions on acid chlorides and esters (carboxyl groups) is similar to that taking place with carbonyl compounds, except that acid chlorides and esters have a leaving group (\u2013Cl and \u2013OR). So the reaction does not stop at formation of the alkoxide ion as a tetrahedral intermediate, but keeps going with an internal nucleophilic displacement of the leaving group. The direct outcome of this process is formation of the corresponding carbonyl compound (aldehyde or ketone), which may or may not undergo further reduction to alcohol, depending on the nature of the reagents used and reaction conditions. The following mechanism illustrates this concept.\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154533\/Figure_8.png\" alt=\"\" width=\"663px\" height=\"176px\" \/>\r\n\r\nFor simplicity, only the hydride ion is shown. If a full reactivity reducing agent such as $$LiAlH_4$$ is used, the reaction does not stop at the aldehyde stage, since the carbonyl carbon of the aldehyde can be attacked by another hydride equivalent. This results in formation of the primary alcohol (after hydrolysis of the alkoxide ion) as the final product.\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154536\/Figure_8.png\" alt=\"\" width=\"702px\" height=\"187px\" \/>\r\n\r\nThe net reaction then is:\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154539\/Figure_9.png\" alt=\"\" width=\"598px\" height=\"152px\" \/>\r\n\r\nThe reaction with an ester is similar, but the leaving group is different (R\u2019O<sup>\u2013<\/sup>). Can you draw the mechanism that leads to formation of the products shown?\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154542\/Figure_10.png\" alt=\"\" width=\"669px\" height=\"147px\" \/>\r\n\r\nNotice that with both (and all) carboxyl groups, hydride reductions lead to formation of primary alcohols only. There is no possibility of forming secondary alcohols by this method because the carboxyl group is at the end of the carbon chain, or else the chain gets broken so that the carboxyl carbon ends up at the end of a chain in the final product.\r\n\r\n<\/div>\r\n<div id=\"section_4\" class=\"mt-section\">\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"813\"]<img class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154553\/Figure_20.png\" alt=\"\" width=\"813\" height=\"845\" \/> Figure 1: HYDRIDE REDUCTIONS OF CARBONYL AND CARBOXYL GROUPS CHART[\/caption]\r\n\r\n<\/div>\r\n<div id=\"section_9\" class=\"mt-section\"><header>\r\n<h2 id=\"title\">Nucleophilic acyl substitution reactions of carboxylic acids<\/h2>\r\n<\/header><section class=\"mt-content-container\">\r\n<div id=\"section_1\" class=\"mt-section\">\r\n<h3 class=\"editable\">Acid anhydride formation<\/h3>\r\nAn acid anhydride (or just anhydride) is the product of formal\u00a0condensation\u00a0of two\u00a0oxoacid\u00a0molecules with the release of a water molecule. The most common anhydrides in organic chemistry are those derived from\u00a0carboxylic acids at high temperatures to remove water.\r\n\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154834\/anhydride.png\" alt=\"\" width=\"493\" height=\"68\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_2\" class=\"mt-section\">\r\n<h3 class=\"editable\">Carboxylic acids react with thionyl Chloride ($$SOCl_2$$) to form <a title=\"Acid Halides\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Acid_Halides\" rel=\"internal\">acid chlorides<\/a><\/h3>\r\nDuring the reaction the hydroxyl group of the carboxylic acid is converted to a chlorosulfite intermediate making it a better leaving group. The chloride anion produced during the reaction acts a nucleophile.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154837\/1.jpg\" alt=\"1.jpg\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_3\" class=\"mt-section\">\r\n<div class=\"textbox examples\">\r\n<h3 class=\"editable\">Example<\/h3>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154839\/2.jpg\" alt=\"2.jpg\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_4\" class=\"mt-section\">\r\n\r\n&nbsp;\r\n<h3 class=\"editable\">Mechanism<\/h3>\r\n1) Nucleophilic attack on Thionyl Chloride\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154841\/3.jpg\" alt=\"3.jpg\" width=\"435\" height=\"110\" \/>\r\n\r\n2) Removal of Cl leaving group\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154843\/4.jpg\" alt=\"4.jpg\" width=\"527\" height=\"138\" \/>\r\n\r\n3) Nucleophilic attack on the carbonyl\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154845\/5.jpg\" alt=\"5.jpg\" width=\"413\" height=\"146\" \/>\r\n\r\n4) Leaving group removal\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154847\/6.jpg\" alt=\"6.jpg\" \/>\r\n\r\n5) Deprotonation\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154850\/7.jpg\" alt=\"7.jpg\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_5\" class=\"mt-section\"><\/div>\r\n<div id=\"section_9\" class=\"mt-section\">\r\n<div id=\"section_10\" class=\"mt-section\"><\/div>\r\n<\/div>\r\n<div id=\"section_11\" class=\"mt-section\">\r\n<h2 class=\"editable\">Conversion of carboxylic acids to amides<\/h2>\r\nThe direct reaction of a carboxylic acid with an amine would be expected to be difficult because the basic amine would deprotonate the carboxylic acid to form a highly unreactive carboxylate.\u00a0 However when the ammonium carboxylate salt is heated to a temperature above 100 <sup>o<\/sup>C water is driven off and an amide is formed.\r\n\r\n<\/div>\r\n<div id=\"section_12\" class=\"mt-section\">\r\n<h3 class=\"editable\">General Reaction<\/h3>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154914\/1.jpg\" alt=\"1.jpg\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_13\" class=\"mt-section\">\r\n<h3 class=\"editable\">Going from reactants to products simply<\/h3>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154916\/2.jpg\" alt=\"2.jpg\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_14\" class=\"mt-section\">\r\n\r\n&nbsp;\r\n<h3 class=\"editable\">Conversion of carboxylic acids to amide using DCC as an activating agent<\/h3>\r\nThe direct conversion of a carboxylic acid to an amide is difficult because amines are basic and tend to convert carboxylic acids to their highly unreactive carboxylates.\u00a0 In this reaction the carboxylic acid adds to the DCC molecule to form a good leaving group which can then be displaced by an amine during nucleophilic substitution.\u00a0 DCC induced coupling to form an amide linkage is an important reaction in the synthesis of peptides.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154918\/1.jpg\" alt=\"1.jpg\" width=\"200\" height=\"213\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_15\" class=\"mt-section\">\r\n<h3 class=\"editable\">Basic reaction<\/h3>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154920\/Fix2.jpg\" alt=\"Fix2.jpg\" width=\"555\" height=\"127\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_16\" class=\"mt-section\">\r\n<h3 class=\"editable\">Going from reactants to products simplified<\/h3>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154923\/3.jpg\" alt=\"3.jpg\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_17\" class=\"mt-section\">\r\n<h3 class=\"editable\">Mechanism<\/h3>\r\n1) Deprotonation\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154925\/4.jpg\" alt=\"4.jpg\" \/>\r\n\r\n2) Nucleophilic attack by the carboxylate\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154928\/5.jpg\" alt=\"5.jpg\" width=\"505\" height=\"181\" \/>\r\n\r\n3) Nucleophilic attack by the amine\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154930\/6.jpg\" alt=\"6.jpg\" width=\"438\" height=\"195\" \/>\r\n\r\n4) Proton transfer\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154932\/7.jpg\" alt=\"7.jpg\" width=\"460\" height=\"166\" \/>\r\n\r\n5) Leaving group removal\r\n\r\n<span class=\"mt-font-times-new-roman\"><img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154935\/8.jpg\" alt=\"8.jpg\" width=\"487\" height=\"279\" \/><\/span>\r\n\r\n<\/div>\r\n<div id=\"section_18\" class=\"mt-section\"><\/div>\r\n<div id=\"section_25\" class=\"mt-section\"><header>\r\n<h2 id=\"title\">Chemistry of Amides<\/h2>\r\n<h3>Preparation of amides<\/h3>\r\n<\/header><section class=\"mt-content-container\">\r\n<div id=\"section_1\" class=\"mt-section\">\r\n\r\nNitriles can be converted to amides. This reaction can be acid or base catalyzed\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155134\/Synth3.jpg\" alt=\"Synth3.jpg\" \/>\r\n\r\nCarboxylic acid can be converted to amides by using DCC as an activating agent\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155137\/Synth4.jpg\" alt=\"Synth4.jpg\" \/>\r\n\r\nDirect conversion of a carboxylic acid to an amide by reaction with an amine.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155139\/Synth6.jpg\" alt=\"Synth6.jpg\" width=\"644px\" height=\"108px\" \/>\r\n\r\nAcid chlorides react with ammonia, 1<sup>o<\/sup> amines and 2<sup>o<\/sup> amines to form amides\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155142\/Synth1.jpg\" alt=\"Synth1.jpg\" \/>\r\n\r\nAcid anhydrides react with ammonia, 1<sup>o<\/sup> amines and 2<sup>o<\/sup> amines to form amides\r\n\r\n<span class=\"mt-font-times-new-roman\"><img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155144\/Synth2.jpg\" alt=\"Synth2.jpg\" \/><\/span>\r\n\r\n<\/div>\r\n<div id=\"section_2\" class=\"mt-section\">\r\n<h3 class=\"editable\">Conversion of amides into carboxylic acids: Hydrolysis<\/h3>\r\n<span class=\"mt-font-size-12\">This page describes the hydrolysis of amides under both acidic and alkaline conditions. It also describes the use of alkaline hydrolysis in testing for amides.<\/span>\r\n\r\n<\/div>\r\n<div id=\"section_3\" class=\"mt-section\">\r\n<h3 class=\"editable\">What is hydrolysis?<\/h3>\r\n<span class=\"mt-font-size-12\">Technically, hydrolysis is a reaction with water. That is exactly what happens when amides are hydrolyzed in the presence of dilute acids such as dilute hydrochloric acid. The acid acts as a catalyst for the reaction between the amide and water. The alkaline hydrolysis of amides actually involves reaction with hydroxide ions, but the result is similar enough that it is still classed as hydrolysis.<\/span>\r\n<div id=\"section_4\" class=\"mt-section\">\r\n<h4 class=\"editable\">Hydrolysis under acidic conditions<\/h4>\r\n<span class=\"mt-font-size-12\">Taking ethanamide as a typical amide. If ethanamide is heated with a dilute acid (such as dilute hydrochloric acid), ethanoic acid is formed together with ammonium ions. So, if you were using hydrochloric acid, the final solution would contain ammonium chloride and ethanoic acid.<\/span>\r\n\r\n\\[ CH_3CONH_2 + H_2O + HCl \\ rightarrow CH_3COOH + NH_4^+Cl^-\\]\r\n\r\n<\/div>\r\n<div id=\"section_5\" class=\"mt-section\">\r\n<h4 class=\"editable\">Hydrolysis under alkaline conditions<\/h4>\r\n<span class=\"mt-font-size-12\">Also, if ethanamide is heated with sodium hydroxide solution, ammonia gas is given off and you are left with a solution containing sodium ethanoate.<\/span>\r\n\r\n\\[ CH_3CONH_2 + NaOH \\ rightarrow CH_3COONa + NH_3\\]\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_6\" class=\"mt-section\">\r\n<h3 class=\"editable\">Conversion of amides into amines: Reduction<\/h3>\r\nAmides can be converted to 1\u00b0, 2\u00b0 or 3\u00b0 amines using LiAlH<sub>4<\/sub>.\r\n<p style=\"text-align: center\"><img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155146\/1.jpg\" alt=\"1.jpg\" \/><\/p>\r\n\r\n<div>\r\n<div id=\"example\">\r\n<div class=\"textbox examples\">\r\n<h3>Examples<\/h3>\r\n<p class=\"boxtitle\">Amide Reductions<\/p>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155148\/2.jpg\" alt=\"2.jpg\" \/>\r\n\r\n<span style=\"font-size: 1rem;text-align: initial;background-color: #ffffff\">Alkyl groups attached to the nitrogen do not affect the reaction.<\/span>\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155150\/3.jpg\" alt=\"3.jpg\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_8\" class=\"mt-section\">\r\n<h3 class=\"editable\">Contributors<\/h3>\r\n<\/div>\r\n<div id=\"section_9\" class=\"mt-section\">\r\n<ul>\r\n \t<li><a class=\"external\" title=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" href=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" target=\"_blank\" rel=\"external nofollow noopener\">Dr. Dietmar Kennepohl<\/a> FCIC (Professor of Chemistry, <a class=\"external\" title=\"http:\/\/www.athabascau.ca\/\" href=\"http:\/\/www.athabascau.ca\/\" target=\"_blank\" rel=\"external nofollow noopener\">Athabasca University<\/a>)<\/li>\r\n \t<li>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/li>\r\n \t<li>Jim Clark (<a class=\"external\" title=\"http:\/\/www.chemguide.co.uk\" href=\"http:\/\/www.chemguide.co.uk\" target=\"_blank\" rel=\"external nofollow noopener\">Chemguide.co.uk<\/a>)<\/li>\r\n<\/ul>\r\n<header><\/header><section class=\"mt-content-container\">\r\n<div id=\"section_5\" class=\"mt-section\">\r\n\r\n&nbsp;\r\n\r\n<header>\r\n<h2 id=\"title\">Grignard reagents convert esters into tertiary alcohols<\/h2>\r\n<dl class=\"mt-last-updated-container\"><\/dl>\r\n<\/header><section class=\"mt-content-container\">As we saw in <a href=\"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/20-3-addition-of-rmgx-rli-to-co\/\">section 20.3<\/a>, the addition of Grignard reagents converts esters to 3<sup>o<\/sup> alcohols.\u00a0 In effect the Grignard reagent adds twice.\u00a0 The initial steps of the mechanism involve a nucleophilic acyl substitution to form a ketone, which then reacts with the second mole of the Grignard reagent.\r\n<div id=\"section_1\" class=\"mt-section\">\r\n<h3 class=\"editable\">General Reaction<\/h3>\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155447\/1.jpg\" alt=\"File:\/C:\\Users\\Gantor\\AppData\\Local\\Temp\\msohtmlclip1\\01\\clip_image002.png\" \/>\r\n<div>\r\n<div id=\"example\">\r\n<div class=\"textbox examples\">\r\n<h3>Examples<\/h3>\r\n<div id=\"section_1\" class=\"mt-section\">\r\n<div id=\"example\">\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155449\/2.jpg\" alt=\"2.jpg\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_3\" class=\"mt-section\">\r\n<h3 class=\"editable\">Contributors<\/h3>\r\nProf. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)\r\n\r\n<header>\r\n<h2 id=\"title\">Claisen condensation<\/h2>\r\n<dl class=\"mt-last-updated-container\"><\/dl>\r\n<\/header><section class=\"mt-content-container\">Earlier, we examined the aldol reactions as a nucleophilic carbonyl addition in section 20.6, in which the electrophile is the carbonyl carbon of an aldehyde or ketone.\u00a0 A nucleophilic enolate can also attack the carbonyl carbon of a carboxylic acid derivative in a nucleophilic <em>acyl substitution<\/em> reaction.<img class=\"\u201cinternal internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155558\/image069.png\" alt=\"image070.png\" width=\"581\" height=\"159\" \/>This is referred to as a <strong>Claisen condensation<\/strong>, after the German chemist Ludwig Claisen (1851-1930).\r\n<div id=\"section_1\" class=\"mt-section\"><\/div>\r\n<div id=\"section_3\" class=\"mt-section\">\r\n<div>\r\n<div class=\"mt-section\"><section class=\"mt-content-container\">\r\n<div id=\"section_1\" class=\"mt-section\">\r\n\r\nBasic reaction\r\n\r\n<img class=\"size-full wp-image-2478 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07202518\/download-4.jpeg\" alt=\"\" width=\"624\" height=\"132\" \/>\r\n\r\nGoing from reactants to products simply\u00a0<img class=\"alignnone size-full wp-image-2482\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07202707\/download-5.jpeg\" alt=\"\" width=\"625\" height=\"140\" \/>\r\n\r\n&nbsp;\r\n<div>\r\n<div id=\"example\">\r\n<div class=\"textbox examples\">\r\n<h3>Example: Claisen Condensation<\/h3>\r\n<img class=\"size-full wp-image-2483 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07202826\/222.jpeg\" alt=\"\" width=\"539\" height=\"96\" \/><img src=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Reactions\/Reactivity_of_Alpha_Hydrogens\/denied:data:image\/jpeg;base64,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#fixme\" alt=\"\" \/>\r\n\r\n<img class=\"size-full wp-image-2481 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07202704\/ex.jpeg\" alt=\"\" width=\"625\" height=\"120\" \/>\r\n\r\n<\/div>\r\n<h3><span style=\"color: #6c64ad;font-size: 1em;font-weight: 600\">Claisen condensation mechanism<\/span><\/h3>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_2\" class=\"mt-section\">\r\n\r\n1) Enolate formation\r\n\r\n<img class=\"size-full wp-image-2484 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07202926\/download-6.jpeg\" alt=\"\" width=\"799\" height=\"147\" \/>\r\n\r\n2) Nucleophilic attack\r\n\r\n<img class=\"alignnone size-full wp-image-2480\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07202700\/21.jpeg\" alt=\"\" width=\"538\" height=\"248\" \/>\r\n\r\n3) Removal of leaving group\r\n\r\n<img class=\"alignnone size-full wp-image-2479\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07202655\/3.jpeg\" alt=\"\" width=\"599\" height=\"159\" \/>\r\n\r\n<\/div>\r\n<div id=\"section_3\" class=\"mt-section\">\r\n<h3 class=\"editable\">Dieckmann Condensation<\/h3>\r\nA diester can undergo an intramolecular reaction called a Dieckmann condensation.\r\n<div>\r\n<div class=\"textbox examples\">\r\n<h3>Example: Dieckman Condensation<\/h3>\r\n<img class=\"size-full wp-image-2485 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07203054\/downex.jpeg\" alt=\"\" width=\"582\" height=\"186\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_4\" class=\"mt-section\">\r\n<h3 class=\"editable\">Crossed Claisen condensation<\/h3>\r\nClaisen condensations between different ester reactants are called <strong>Crossed<\/strong> <strong>Claisen <\/strong>reactions. Crossed Claisen reactions in which both reactants can serve as donors and acceptors generally give complex mixtures. Because of this most Crossed Claisen reactions are usually not performed unless one reactant has no alpha hydrogens.\r\n<div>\r\n<div class=\"textbox examples\">\r\n<h3 class=\"boxtitle\">Example : Crossed Claisen Condensation<\/h3>\r\n<img class=\"size-full wp-image-2486 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07203139\/download-7.jpeg\" alt=\"\" width=\"625\" height=\"102\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_5\" class=\"mt-section\">\r\n<h3 class=\"editable\">Contributors<\/h3>\r\n<ul>\r\n \t<li>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/section><\/div>\r\n<\/div>\r\n<\/div>\r\n<\/section><\/div>\r\n<\/section><\/div>\r\n<\/section><\/div>\r\n<\/section><\/div>\r\n<\/section><\/div>\r\n<\/div>\r\n<\/section><\/div>\r\n<\/section><\/div>\r\n<\/section><\/div>\r\n<\/section><\/div>\r\n<\/section><\/div>\r\n<\/section><\/article>","rendered":"<header>\n<div>\n<h2>Transesterification<\/h2>\n<\/div>\n<\/header>\n<article id=\"elm-main-content\" class=\"elm-content-container\">\n<section class=\"mt-content-container\">Transesterification is the conversion of a carboxylic acid ester into a different carboxylic acid ester.<\/p>\n<div id=\"section_1\" class=\"mt-section\">\n<h3 class=\"editable\">Introduction<\/h3>\n<p>When in ester is placed in a large excess of an alcohol along with presence of either an acid or a base there can be an exchange of alkoxy groups. The large excess of alcohol is used to drive the reaction forward. The most common method of transesterification is the reaction of the ester with an alcohol in the presence of an acid catalyst e.g.:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153544\/transesterification1.png\" alt=\"\" width=\"644\" height=\"77\" \/><\/p>\n<p>This reaction has the following mechanism:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153547\/transesterification2.png\" alt=\"\" width=\"626\" height=\"595\" \/><\/p>\n<p>Since both the reactants and the products are an ester and an alcohol, the reaction is reversible and the equilibrium constant is close to one. \u00a0Consequently, the <a title=\"Le Ch\u00e2telier's Principle\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Physical_and_Theoretical_Chemistry_Textbook_Maps\/Supplemental_Modules_(Physical_and_Theoretical_Chemistry)\/Equilibria\/Le_Chatelier's_Principle\" rel=\"internal\">Le Chatelier\u2019s principle<\/a> has to be exploited to drive the reaction to completion. The simplest way to do so is to use the alcohol as the solvent as well.<\/p>\n<div id=\"section_2\" class=\"mt-section\">\n<h4 class=\"editable\">General reaction<\/h4>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153550\/1.jpg\" alt=\"1.jpg\" \/><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153552\/2.jpg\" alt=\"2.jpg\" \/><\/p>\n<\/div>\n<\/div>\n<div id=\"section_3\" class=\"mt-section\">\n<h3 class=\"editable\">Mechanism in basic conditions<\/h3>\n<p>Nucleophilic attack by an alkoxide<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153554\/3.jpg\" alt=\"3.jpg\" \/><\/p>\n<p>2) Leaving group removal<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153556\/4.jpg\" alt=\"4.jpg\" \/><\/p>\n<\/div>\n<div id=\"section_4\" class=\"mt-section\"><\/div>\n<div id=\"section_5\" class=\"mt-section\">\n<h3 class=\"editable\">Contributors<\/h3>\n<p>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/p>\n<ul>\n<li><a class=\"external\" title=\"http:\/\/www.uvu.edu\/profpages\/profiles\/show\/user_id\/1776\" href=\"http:\/\/www.uvu.edu\/profpages\/profiles\/show\/user_id\/1776\" target=\"_blank\" rel=\"external nofollow noopener\"><span class=\"gD\">Gamini Gunawardena<\/span><\/a> from the <a class=\"external\" title=\"http:\/\/science.uvu.edu\/ochem\/\" href=\"http:\/\/science.uvu.edu\/ochem\/\" target=\"_blank\" rel=\"external nofollow noopener\">OChemPal <\/a>site (<a class=\"external\" title=\"http:\/\/www.uvu.edu\/chemistry\/\" href=\"http:\/\/www.uvu.edu\/chemistry\/\" target=\"_blank\" rel=\"external nofollow noopener\">Utah Valley University<\/a>)<\/li>\n<\/ul>\n<header>\n<h2 id=\"title\">Saponification<\/h2>\n<dl class=\"mt-last-updated-container\"><\/dl>\n<\/header>\n<section class=\"mt-content-container\"><a title=\"Esters\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Esters\" rel=\"internal\">Esters <\/a>can be cleaved back into a carboxylic acid and an alcohol by reaction with water and a base. The reaction is called a saponification from the Latin <em>sapo <\/em>which means soap. The name comes from the fact that soap used to me made by the ester hydrolysis of fats. Due to the basic conditions a carboxylate ion is made rather than a <a title=\"Carboxylic Acids\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Carboxylic_Acids\" rel=\"internal\">carboxylic acid.<\/a><\/p>\n<div id=\"section_1\" class=\"mt-section\">\n<h3 class=\"editable\">General reaction<\/h3>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153742\/1.jpg\" alt=\"1.jpg\" \/><\/p>\n<div class=\"textbox examples\">\n<h3>Example<\/h3>\n<p><img decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153744\/2.jpg\" alt=\"2.jpg\" \/><\/p>\n<\/div>\n<\/div>\n<div id=\"section_2\" class=\"mt-section\">\n<h3 class=\"editable\">Mechanism<\/h3>\n<p>1)\u00a0 Nucleophilic attack by hydroxide<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153747\/3.jpg\" alt=\"3.jpg\" width=\"371\" height=\"177\" \/><\/p>\n<p>2) Leaving group removal<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153749\/4a.jpg\" alt=\"4a.jpg\" width=\"510\" height=\"137\" \/><\/p>\n<p>3)\u00a0 Deprotonation<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30153751\/5.jpg\" alt=\"5.jpg\" \/><\/p>\n<\/div>\n<div id=\"section_3\" class=\"mt-section\">\n<h3 class=\"editable\">Contributors<\/h3>\n<p>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/p>\n<h2>Alkaline hydrolysis of amides<\/h2>\n<p>In alkaline hydrolysis the amide is heated with boiling aqueous sodium or potassium hydroxide. The nucleophilic hydroxide ion adds to the carbonyl carbon to form a tetrahedral intermediate, which, with the help of the aqueous solvent, expels the nitrogen as the free amine:<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30160907\/Roberts_and_Caserio_Screenshot_24-4-3.jpg\" alt=\"\" width=\"491px\" height=\"112px\" \/><\/p>\n<section class=\"mt-content-container\">\n<div class=\"mt-section\">\n<header>\n<h2 id=\"title\">Reduction of carboxylic acids and their derivatives<\/h2>\n<\/header>\n<section class=\"mt-content-container\">\n<div id=\"section_1\" class=\"mt-section\">\n<h3 class=\"editable\">Reduction of acid chlorides and esters<\/h3>\n<p>Acid (acyl) chlorides can be converted to\u00a0aldehydes using lithium tri-tert-butoxyaluminium hydride (LiAlH(Ot-Bu)<sub>3<\/sub>). The hydride source (LiAlH(Ot-Bu)<sub>3<\/sub>) is a weaker reducing agent than lithium aluminum hydride. Because acid chlorides are highly activated they\u00a0still react with the hydride source;\u00a0however, the formed aldehyde will react slowly, which allows for its isolation.<\/p>\n<p>General reaction:<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154120\/1.jpg\" alt=\"1.jpg\" width=\"392px\" height=\"135px\" \/><\/p>\n<div class=\"textbox examples\">\n<h3>Example<\/h3>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154122\/2.jpg\" alt=\"2.jpg\" width=\"459px\" height=\"119px\" \/><\/p>\n<\/div>\n<p><span style=\"font-size: 1rem;text-align: initial\">Acid chlorides can be converted to\u00a0aldehydes using lithium tri-tert-butoxyaluminium hydride (LiAlH(Ot-Bu)<\/span><sub style=\"text-align: initial\">3<\/sub><span style=\"font-size: 1rem;text-align: initial\">). The hydride source (LiAlH(Ot-Bu)<\/span><sub style=\"text-align: initial\">3<\/sub><span style=\"font-size: 1rem;text-align: initial\">) is a weaker reducing agent than lithium aluminum hydride. Because acid chlorides are highly activated they\u00a0still react with the hydride source;\u00a0however, the formed aldehyde will react slowly, which allows for its isolation.<\/span><\/p>\n<p>General Reaction:<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154120\/1.jpg\" alt=\"1.jpg\" width=\"392px\" height=\"135px\" \/><\/p>\n<div class=\"textbox examples\">\n<h3>Example<\/h3>\n<p><img decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154122\/2.jpg\" alt=\"2.jpg\" width=\"459px\" height=\"119px\" \/><\/p>\n<\/div>\n<p>&nbsp;<\/p>\n<p>Esters can be converted to aldehydes using diisobutylaluminium hydride (DIBAH). \u00a0The reaction is usually carried out at -78 <sup>o<\/sup>C to prevent reaction with the aldehyde product.<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154125\/1.jpg\" alt=\"1.jpg\" \/><\/p>\n<div class=\"textbox examples\">\n<h3>Example<\/h3>\n<p><img decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154127\/2.jpg\" alt=\"2.jpg\" \/><\/p>\n<\/div>\n<p>&nbsp;<\/p>\n<p>Esters can be converted to 1<sup>o<\/sup> alcohols using LiAlH<sub>4<\/sub>, while sodium borohydride ($$NaBH_4$$) is not a strong enough reducing agent to perform this reaction.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154129\/1.jpg\" alt=\"1.jpg\" width=\"475\" height=\"113\" \/><\/p>\n<div class=\"textbox examples\">\n<h3>Example<\/h3>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154132\/2.jpg\" alt=\"2.jpg\" \/><\/p>\n<\/div>\n<\/div>\n<div id=\"section_2\" class=\"mt-section\">\n<h3 class=\"editable\">Mechanism<\/h3>\n<p>1) Nucleophilic attack by the hydride<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154135\/3.jpg\" alt=\"3.jpg\" \/><\/p>\n<p>2) Leaving group removal<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154139\/4.jpg\" alt=\"4.jpg\" width=\"515\" height=\"142\" \/><\/p>\n<p>3) Nucleophilic attack by the hydride anion<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154142\/5.jpg\" alt=\"5.jpg\" width=\"463\" height=\"204\" \/><\/p>\n<p>4) The alkoxide is protonated<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154144\/6.jpg\" alt=\"6.jpg\" \/><\/p>\n<\/div>\n<div id=\"section_4\" class=\"mt-section\">\n<h3 class=\"editable\"><strong>Going from reactant to products simplified<\/strong><\/h3>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154149\/2.jpg\" alt=\"2.jpg\" width=\"644px\" height=\"71px\" \/><\/p>\n<div class=\"textbox examples\">\n<h3>Example<\/h3>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154151\/3.jpg\" alt=\"3.jpg\" \/><\/p>\n<\/div>\n<\/div>\n<div id=\"section_6\" class=\"mt-section\">\n<h3><\/h3>\n<h2 class=\"editable\">Reduction of amides using LiAlH<sub>4<\/sub>.<\/h2>\n<\/div>\n<div id=\"section_7\" class=\"mt-section\">\n<h3 class=\"editable\">General Reaction<\/h3>\n<p style=\"text-align: center\"><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154225\/1.jpg\" alt=\"1.jpg\" \/><\/p>\n<div class=\"textbox examples\">\n<h3>Example: Amide Reduction<\/h3>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154227\/2.jpg\" alt=\"2.jpg\" \/><\/p>\n<p>Alkyl groups attached to the nitrogen do not affect the reaction.<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154229\/3.jpg\" alt=\"3.jpg\" \/><\/p>\n<\/div>\n<\/div>\n<div id=\"section_8\" class=\"mt-section\">\n<p>&nbsp;<\/p>\n<h3 class=\"editable\">Mechanism<\/h3>\n<p>1) Nucleophilic attack by the hydride<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154231\/4.jpg\" alt=\"4.jpg\" \/><\/p>\n<p>2) Leaving group removal<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154234\/5.jpg\" alt=\"5.jpg\" \/><\/p>\n<p>3) Nucleophilic attack by the hydride<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154236\/6.jpg\" alt=\"6.jpg\" \/><\/p>\n<\/div>\n<div id=\"section_9\" class=\"mt-section\">\n<h3 class=\"editable\">Contributors<\/h3>\n<ul>\n<li>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/li>\n<\/ul>\n<header><\/header>\n<section class=\"mt-content-container\">\n<div id=\"section_3\" class=\"mt-section\">\n<section class=\"mt-content-container\">\n<div id=\"s66923\" class=\"mt-include\">\n<div id=\"section_2\" class=\"mt-section\">\n<h3><\/h3>\n<h2 id=\"REACTIONS_WITH_ACID_CHLORIDES_AND_ESTERS-66923\">Reduction of acid chlorides and esters using LiAlH<sub>4<\/sub><\/h2>\n<p>The mechanism of action of hydride reductions on acid chlorides and esters (carboxyl groups) is similar to that taking place with carbonyl compounds, except that acid chlorides and esters have a leaving group (\u2013Cl and \u2013OR). So the reaction does not stop at formation of the alkoxide ion as a tetrahedral intermediate, but keeps going with an internal nucleophilic displacement of the leaving group. The direct outcome of this process is formation of the corresponding carbonyl compound (aldehyde or ketone), which may or may not undergo further reduction to alcohol, depending on the nature of the reagents used and reaction conditions. The following mechanism illustrates this concept.<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154533\/Figure_8.png\" alt=\"\" width=\"663px\" height=\"176px\" \/><\/p>\n<p>For simplicity, only the hydride ion is shown. If a full reactivity reducing agent such as $$LiAlH_4$$ is used, the reaction does not stop at the aldehyde stage, since the carbonyl carbon of the aldehyde can be attacked by another hydride equivalent. This results in formation of the primary alcohol (after hydrolysis of the alkoxide ion) as the final product.<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154536\/Figure_8.png\" alt=\"\" width=\"702px\" height=\"187px\" \/><\/p>\n<p>The net reaction then is:<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154539\/Figure_9.png\" alt=\"\" width=\"598px\" height=\"152px\" \/><\/p>\n<p>The reaction with an ester is similar, but the leaving group is different (R\u2019O<sup>\u2013<\/sup>). Can you draw the mechanism that leads to formation of the products shown?<\/p>\n<p><img decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154542\/Figure_10.png\" alt=\"\" width=\"669px\" height=\"147px\" \/><\/p>\n<p>Notice that with both (and all) carboxyl groups, hydride reductions lead to formation of primary alcohols only. There is no possibility of forming secondary alcohols by this method because the carboxyl group is at the end of the carbon chain, or else the chain gets broken so that the carboxyl carbon ends up at the end of a chain in the final product.<\/p>\n<\/div>\n<div id=\"section_4\" class=\"mt-section\">\n<div style=\"width: 823px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" class=\"internal\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154553\/Figure_20.png\" alt=\"\" width=\"813\" height=\"845\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 1: HYDRIDE REDUCTIONS OF CARBONYL AND CARBOXYL GROUPS CHART<\/p>\n<\/div>\n<\/div>\n<div id=\"section_9\" class=\"mt-section\">\n<header>\n<h2 id=\"title\">Nucleophilic acyl substitution reactions of carboxylic acids<\/h2>\n<\/header>\n<section class=\"mt-content-container\">\n<div id=\"section_1\" class=\"mt-section\">\n<h3 class=\"editable\">Acid anhydride formation<\/h3>\n<p>An acid anhydride (or just anhydride) is the product of formal\u00a0condensation\u00a0of two\u00a0oxoacid\u00a0molecules with the release of a water molecule. The most common anhydrides in organic chemistry are those derived from\u00a0carboxylic acids at high temperatures to remove water.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154834\/anhydride.png\" alt=\"\" width=\"493\" height=\"68\" \/><\/p>\n<\/div>\n<div id=\"section_2\" class=\"mt-section\">\n<h3 class=\"editable\">Carboxylic acids react with thionyl Chloride ($$SOCl_2$$) to form <a title=\"Acid Halides\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Acid_Halides\" rel=\"internal\">acid chlorides<\/a><\/h3>\n<p>During the reaction the hydroxyl group of the carboxylic acid is converted to a chlorosulfite intermediate making it a better leaving group. The chloride anion produced during the reaction acts a nucleophile.<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154837\/1.jpg\" alt=\"1.jpg\" \/><\/p>\n<\/div>\n<div id=\"section_3\" class=\"mt-section\">\n<div class=\"textbox examples\">\n<h3 class=\"editable\">Example<\/h3>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154839\/2.jpg\" alt=\"2.jpg\" \/><\/p>\n<\/div>\n<\/div>\n<div id=\"section_4\" class=\"mt-section\">\n<p>&nbsp;<\/p>\n<h3 class=\"editable\">Mechanism<\/h3>\n<p>1) Nucleophilic attack on Thionyl Chloride<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154841\/3.jpg\" alt=\"3.jpg\" width=\"435\" height=\"110\" \/><\/p>\n<p>2) Removal of Cl leaving group<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154843\/4.jpg\" alt=\"4.jpg\" width=\"527\" height=\"138\" \/><\/p>\n<p>3) Nucleophilic attack on the carbonyl<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154845\/5.jpg\" alt=\"5.jpg\" width=\"413\" height=\"146\" \/><\/p>\n<p>4) Leaving group removal<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154847\/6.jpg\" alt=\"6.jpg\" \/><\/p>\n<p>5) Deprotonation<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154850\/7.jpg\" alt=\"7.jpg\" \/><\/p>\n<\/div>\n<div id=\"section_5\" class=\"mt-section\"><\/div>\n<div id=\"section_9\" class=\"mt-section\">\n<div id=\"section_10\" class=\"mt-section\"><\/div>\n<\/div>\n<div id=\"section_11\" class=\"mt-section\">\n<h2 class=\"editable\">Conversion of carboxylic acids to amides<\/h2>\n<p>The direct reaction of a carboxylic acid with an amine would be expected to be difficult because the basic amine would deprotonate the carboxylic acid to form a highly unreactive carboxylate.\u00a0 However when the ammonium carboxylate salt is heated to a temperature above 100 <sup>o<\/sup>C water is driven off and an amide is formed.<\/p>\n<\/div>\n<div id=\"section_12\" class=\"mt-section\">\n<h3 class=\"editable\">General Reaction<\/h3>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154914\/1.jpg\" alt=\"1.jpg\" \/><\/p>\n<\/div>\n<div id=\"section_13\" class=\"mt-section\">\n<h3 class=\"editable\">Going from reactants to products simply<\/h3>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154916\/2.jpg\" alt=\"2.jpg\" \/><\/p>\n<\/div>\n<div id=\"section_14\" class=\"mt-section\">\n<p>&nbsp;<\/p>\n<h3 class=\"editable\">Conversion of carboxylic acids to amide using DCC as an activating agent<\/h3>\n<p>The direct conversion of a carboxylic acid to an amide is difficult because amines are basic and tend to convert carboxylic acids to their highly unreactive carboxylates.\u00a0 In this reaction the carboxylic acid adds to the DCC molecule to form a good leaving group which can then be displaced by an amine during nucleophilic substitution.\u00a0 DCC induced coupling to form an amide linkage is an important reaction in the synthesis of peptides.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154918\/1.jpg\" alt=\"1.jpg\" width=\"200\" height=\"213\" \/><\/p>\n<\/div>\n<div id=\"section_15\" class=\"mt-section\">\n<h3 class=\"editable\">Basic reaction<\/h3>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154920\/Fix2.jpg\" alt=\"Fix2.jpg\" width=\"555\" height=\"127\" \/><\/p>\n<\/div>\n<div id=\"section_16\" class=\"mt-section\">\n<h3 class=\"editable\">Going from reactants to products simplified<\/h3>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154923\/3.jpg\" alt=\"3.jpg\" \/><\/p>\n<\/div>\n<div id=\"section_17\" class=\"mt-section\">\n<h3 class=\"editable\">Mechanism<\/h3>\n<p>1) Deprotonation<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154925\/4.jpg\" alt=\"4.jpg\" \/><\/p>\n<p>2) Nucleophilic attack by the carboxylate<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154928\/5.jpg\" alt=\"5.jpg\" width=\"505\" height=\"181\" \/><\/p>\n<p>3) Nucleophilic attack by the amine<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154930\/6.jpg\" alt=\"6.jpg\" width=\"438\" height=\"195\" \/><\/p>\n<p>4) Proton transfer<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154932\/7.jpg\" alt=\"7.jpg\" width=\"460\" height=\"166\" \/><\/p>\n<p>5) Leaving group removal<\/p>\n<p><span class=\"mt-font-times-new-roman\"><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30154935\/8.jpg\" alt=\"8.jpg\" width=\"487\" height=\"279\" \/><\/span><\/p>\n<\/div>\n<div id=\"section_18\" class=\"mt-section\"><\/div>\n<div id=\"section_25\" class=\"mt-section\">\n<header>\n<h2 id=\"title\">Chemistry of Amides<\/h2>\n<h3>Preparation of amides<\/h3>\n<\/header>\n<section class=\"mt-content-container\">\n<div id=\"section_1\" class=\"mt-section\">\n<p>Nitriles can be converted to amides. This reaction can be acid or base catalyzed<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155134\/Synth3.jpg\" alt=\"Synth3.jpg\" \/><\/p>\n<p>Carboxylic acid can be converted to amides by using DCC as an activating agent<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155137\/Synth4.jpg\" alt=\"Synth4.jpg\" \/><\/p>\n<p>Direct conversion of a carboxylic acid to an amide by reaction with an amine.<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155139\/Synth6.jpg\" alt=\"Synth6.jpg\" width=\"644px\" height=\"108px\" \/><\/p>\n<p>Acid chlorides react with ammonia, 1<sup>o<\/sup> amines and 2<sup>o<\/sup> amines to form amides<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155142\/Synth1.jpg\" alt=\"Synth1.jpg\" \/><\/p>\n<p>Acid anhydrides react with ammonia, 1<sup>o<\/sup> amines and 2<sup>o<\/sup> amines to form amides<\/p>\n<p><span class=\"mt-font-times-new-roman\"><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155144\/Synth2.jpg\" alt=\"Synth2.jpg\" \/><\/span><\/p>\n<\/div>\n<div id=\"section_2\" class=\"mt-section\">\n<h3 class=\"editable\">Conversion of amides into carboxylic acids: Hydrolysis<\/h3>\n<p><span class=\"mt-font-size-12\">This page describes the hydrolysis of amides under both acidic and alkaline conditions. It also describes the use of alkaline hydrolysis in testing for amides.<\/span><\/p>\n<\/div>\n<div id=\"section_3\" class=\"mt-section\">\n<h3 class=\"editable\">What is hydrolysis?<\/h3>\n<p><span class=\"mt-font-size-12\">Technically, hydrolysis is a reaction with water. That is exactly what happens when amides are hydrolyzed in the presence of dilute acids such as dilute hydrochloric acid. The acid acts as a catalyst for the reaction between the amide and water. The alkaline hydrolysis of amides actually involves reaction with hydroxide ions, but the result is similar enough that it is still classed as hydrolysis.<\/span><\/p>\n<div id=\"section_4\" class=\"mt-section\">\n<h4 class=\"editable\">Hydrolysis under acidic conditions<\/h4>\n<p><span class=\"mt-font-size-12\">Taking ethanamide as a typical amide. If ethanamide is heated with a dilute acid (such as dilute hydrochloric acid), ethanoic acid is formed together with ammonium ions. So, if you were using hydrochloric acid, the final solution would contain ammonium chloride and ethanoic acid.<\/span><\/p>\n<p>\\[ CH_3CONH_2 + H_2O + HCl \\ rightarrow CH_3COOH + NH_4^+Cl^-\\]<\/p>\n<\/div>\n<div id=\"section_5\" class=\"mt-section\">\n<h4 class=\"editable\">Hydrolysis under alkaline conditions<\/h4>\n<p><span class=\"mt-font-size-12\">Also, if ethanamide is heated with sodium hydroxide solution, ammonia gas is given off and you are left with a solution containing sodium ethanoate.<\/span><\/p>\n<p>\\[ CH_3CONH_2 + NaOH \\ rightarrow CH_3COONa + NH_3\\]<\/p>\n<\/div>\n<\/div>\n<div id=\"section_6\" class=\"mt-section\">\n<h3 class=\"editable\">Conversion of amides into amines: Reduction<\/h3>\n<p>Amides can be converted to 1\u00b0, 2\u00b0 or 3\u00b0 amines using LiAlH<sub>4<\/sub>.<\/p>\n<p style=\"text-align: center\"><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155146\/1.jpg\" alt=\"1.jpg\" \/><\/p>\n<div>\n<div id=\"example\">\n<div class=\"textbox examples\">\n<h3>Examples<\/h3>\n<p class=\"boxtitle\">Amide Reductions<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155148\/2.jpg\" alt=\"2.jpg\" \/><\/p>\n<p><span style=\"font-size: 1rem;text-align: initial;background-color: #ffffff\">Alkyl groups attached to the nitrogen do not affect the reaction.<\/span><\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155150\/3.jpg\" alt=\"3.jpg\" \/><\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_8\" class=\"mt-section\">\n<h3 class=\"editable\">Contributors<\/h3>\n<\/div>\n<div id=\"section_9\" class=\"mt-section\">\n<ul>\n<li><a class=\"external\" title=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" href=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" target=\"_blank\" rel=\"external nofollow noopener\">Dr. Dietmar Kennepohl<\/a> FCIC (Professor of Chemistry, <a class=\"external\" title=\"http:\/\/www.athabascau.ca\/\" href=\"http:\/\/www.athabascau.ca\/\" target=\"_blank\" rel=\"external nofollow noopener\">Athabasca University<\/a>)<\/li>\n<li>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/li>\n<li>Jim Clark (<a class=\"external\" title=\"http:\/\/www.chemguide.co.uk\" href=\"http:\/\/www.chemguide.co.uk\" target=\"_blank\" rel=\"external nofollow noopener\">Chemguide.co.uk<\/a>)<\/li>\n<\/ul>\n<header><\/header>\n<section class=\"mt-content-container\">\n<div id=\"section_5\" class=\"mt-section\">\n<p>&nbsp;<\/p>\n<header>\n<h2 id=\"title\">Grignard reagents convert esters into tertiary alcohols<\/h2>\n<dl class=\"mt-last-updated-container\"><\/dl>\n<\/header>\n<section class=\"mt-content-container\">As we saw in <a href=\"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/20-3-addition-of-rmgx-rli-to-co\/\">section 20.3<\/a>, the addition of Grignard reagents converts esters to 3<sup>o<\/sup> alcohols.\u00a0 In effect the Grignard reagent adds twice.\u00a0 The initial steps of the mechanism involve a nucleophilic acyl substitution to form a ketone, which then reacts with the second mole of the Grignard reagent.<\/p>\n<div id=\"section_1\" class=\"mt-section\">\n<h3 class=\"editable\">General Reaction<\/h3>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155447\/1.jpg\" alt=\"File:\/C:\\Users\\Gantor\\AppData\\Local\\Temp\\msohtmlclip1\\01\\clip_image002.png\" \/><\/p>\n<div>\n<div id=\"example\">\n<div class=\"textbox examples\">\n<h3>Examples<\/h3>\n<div id=\"section_1\" class=\"mt-section\">\n<div id=\"example\">\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155449\/2.jpg\" alt=\"2.jpg\" \/><\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_3\" class=\"mt-section\">\n<h3 class=\"editable\">Contributors<\/h3>\n<p>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/p>\n<header>\n<h2 id=\"title\">Claisen condensation<\/h2>\n<dl class=\"mt-last-updated-container\"><\/dl>\n<\/header>\n<section class=\"mt-content-container\">Earlier, we examined the aldol reactions as a nucleophilic carbonyl addition in section 20.6, in which the electrophile is the carbonyl carbon of an aldehyde or ketone.\u00a0 A nucleophilic enolate can also attack the carbonyl carbon of a carboxylic acid derivative in a nucleophilic <em>acyl substitution<\/em> reaction.<img loading=\"lazy\" decoding=\"async\" class=\"\u201cinternal internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30155558\/image069.png\" alt=\"image070.png\" width=\"581\" height=\"159\" \/>This is referred to as a <strong>Claisen condensation<\/strong>, after the German chemist Ludwig Claisen (1851-1930).<\/p>\n<div id=\"section_1\" class=\"mt-section\"><\/div>\n<div id=\"section_3\" class=\"mt-section\">\n<div>\n<div class=\"mt-section\">\n<section class=\"mt-content-container\">\n<div id=\"section_1\" class=\"mt-section\">\n<p>Basic reaction<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"size-full wp-image-2478 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07202518\/download-4.jpeg\" alt=\"\" width=\"624\" height=\"132\" \/><\/p>\n<p>Going from reactants to products simply\u00a0<img loading=\"lazy\" decoding=\"async\" class=\"alignnone size-full wp-image-2482\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07202707\/download-5.jpeg\" alt=\"\" width=\"625\" height=\"140\" \/><\/p>\n<p>&nbsp;<\/p>\n<div>\n<div id=\"example\">\n<div class=\"textbox examples\">\n<h3>Example: Claisen Condensation<\/h3>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"size-full wp-image-2483 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07202826\/222.jpeg\" alt=\"\" width=\"539\" height=\"96\" \/><img decoding=\"async\" src=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Reactions\/Reactivity_of_Alpha_Hydrogens\/denied:data:image\/jpeg;base64,\/9j\/4AAQSkZJRgABAQEAYABgAAD\/2wBDAAIBAQIBAQICAgICAgICAwUDAwMDAwYEBAMFBwYHBwcGBwcICQsJCAgKCAcHCg0KCgsMDAwMBwkODw0MDgsMDAz\/2wBDAQICAgMDAwYDAwYMCAcIDAwMDAwMDAwMDAwMDAwMDAwMDAwMDAwMDAwMDAwMDAwMDAwMDAwMDAwMDAwMDAwMDAz\/wAARCABgAhsDASIAAhEBAxEB\/8QAHwAAAQUBAQEBAQEAAAAAAAAAAAECAwQFBgcICQoL\/8QAtRAAAgEDAwIEAwUFBAQAAAF9AQIDAAQRBRIhMUEGE1FhByJxFDKBkaEII0KxwRVS0fAkM2JyggkKFhcYGRolJicoKSo0NTY3ODk6Q0RFRkdISUpTVFVWV1hZWmNkZWZnaGlqc3R1dnd4eXqDhIWGh4iJipKTlJWWl5iZmqKjpKWmp6ipqrKztLW2t7i5usLDxMXGx8jJytLT1NXW19jZ2uHi4+Tl5ufo6erx8vP09fb3+Pn6\/8QAHwEAAwEBAQEBAQEBAQAAAAAAAAECAwQFBgcICQoL\/8QAtREAAgECBAQDBAcFBAQAAQJ3AAECAxEEBSExBhJBUQdhcRMiMoEIFEKRobHBCSMzUvAVYnLRChYkNOEl8RcYGRomJygpKjU2Nzg5OkNERUZHSElKU1RVVldYWVpjZGVmZ2hpanN0dXZ3eHl6goOEhYaHiImKkpOUlZaXmJmaoqOkpaanqKmqsrO0tba3uLm6wsPExcbHyMnK0tPU1dbX2Nna4uPk5ebn6Onq8vP09fb3+Pn6\/9oADAMBAAIRAxEAPwD9\/KKKKACiiigAooooAKKKKACiiigAor81dJ+J\/wC1Z\/wVQ+Nnxbv\/AIJfHHQ\/2cvhV8JvFN54F0t28CWnibVPGGo2YRby4uPthCW8CSnZEYsswL71yqk\/RX\/BKf8AbO8Y\/te\/BfxdZ\/EzSNE0X4qfCjxfqHgbxbFopkOl3V5alGW6tRITIIZYZYnAfByW4AwKaV1+Py7\/AJfeN6f11PqCiiikIKKKKACiiigAooooAKKKKACiiigAooooAKKKKACiiigAooooAKKKKACiiigAooooAKKKKACiiigAooooAK5n40fF3QvgB8IfFHjnxRd\/YPDvg\/S7nWNTuNpYw28ETSyMAOSdqnAHU8V01eY\/trfs\/SftX\/sgfE\/4ZQ3y6bP4+8L6hoMN2wytvJcW7xI7cH5QzAnAJxmlJuzsVG11c+CYv+Cl37cZ\/Z5P7Tp+CXwTf9nw6cfE6+Chrd+vxDOg+XvF39o50\/zPKxdeXs3mL93s8zmv0g+DfxY0X48\/CTwx438OXD3WgeL9KttZ06Z0MbSW9xEssZKnlTtYZB6Gvyuj\/ba\/aRt\/2BR+yr\/wyR8a2+PieGP+FejxINJi\/wCFdkfZ\/so1P+2fM8vZ9l\/fbNmPN\/dbs81+lX7Gf7P\/APwyj+yT8NPhmbxNRfwF4Z0\/QXukUoty9vbpE0gBJIDMpIBJwDWjtZ226Pv\/AFp95Pa+\/X+vvPS6KKKgAooooAKKKKAPlb\/gpT+3p4r\/AGYdX+HHw0+EvhXSPHHxz+NN\/c6f4U03WLtrXSdOhtofNu9TvnTDm2t0KM0cZWSTdhDu4PB\/s1ft3ftA\/Cn9sjwr8Cv2rPB\/wtstc+J9hfal4I8W\/Da7vpND1CSzjR7jTZ4L0G4juEjLTeaSsbqyooLBjUX\/AAVi+FXxN+H\/AO0r8A\/2mfhp4M1P4nf8KSl1ew8UeEdK2tq+paPqUMUc89jGf9fcw+SGWFTukJVR1JHCfDPxf8Sf+CrP\/BSX4OfEqT4KfFP4KfCD9nuHVdRM3xJ0YaJrniPWr61+ypBBZ+YzC3ihcyefllZiyYBUVUbX\/P8Ar+rvQp26\/wBP+vw1P0loooqSQooooAKKKKACiiigAooooAKKKKACiiigAooooAKKKKACiiigAooooA\/NDQfhX+1j\/wAErPjf8XbL4L\/BTQ\/2kfhV8W\/FV7450mL\/AITiz8L6l4N1C7Ia7t7j7YCtzC8m1o\/KOQEfcVLAD6L\/AOCTf7GXjP8AZC+Bnim9+KGr6TrXxX+LHiy+8c+L5dJDDTrW9utii1tiwDmKKKKNAWychsEjBrtfH3izVbP\/AIKSfCfQotT1CLRNS+GvjS\/u9PS4dbS6uINU8JpBNJEDseSNLm4VHIJUTygEB2zn\/wDBJ3\/lFl+zT\/2Srwv\/AOmi1pp2X4fLt+X3Dbv+fzPf6KKKQgooooAKKKKACiiigAooooAKKKKACsvxz4p\/4QfwVrGtf2dqusf2RZTXv2DTLf7Re3vloX8qCPI3ytjaq5GWIGRWpRQxp66n57f8E0P27\/j3+1D\/AMFJvj\/4K+LXhwfDTQfC\/hvRNU8N+C2ksr280OO6Mw8+5uoVJkuJlRZGj3skWVQDcrFvZv8Agkv+1d4p\/af+APiqw8fXUeofED4U+N9Z8BeIL5II4F1OaxuCIroRxqiKZLd4WYKiru3YVRgDD\/Z6\/Zd8deBP+Cxv7Q3xW1bQ\/svgHxz4T8Oabomqfbbd\/ttxaLKLhPJWQzJs3LzIig54Jrkv+CFHhu4v\/Cn7R3xCMRTSPil8b\/Eus6LIFVY7uyhljslnTaACrvbS\/N\/FjOTnNOGq17P\/ANK0\/Acklf1X\/pOv4njX\/BOj\/grt8T\/FH\/BU343fCX4wXTX3w31D4hat4P8AhrrzWFrawafqVgTM2iySQqhd5LV45ImmBd2idQ7kkL2n7EH\/AAV2vvBv\/BO\/xT8V\/jhqfiTxzrUPxT1nwV4f0zw7oEM+s67Il40Vjptna26RLLMVVgC2CQpLOTWJ8LP+CSHjj4jfBf8Aa78PeLrE+B\/EvjX41aj8SPhb4hS7trqXT7qNIH03U0EMjGPE0bK0cmxyjOCoDV4h8Hv+Cfv7a3wb\/wCCQ3hLwpY6BrsPxJg+Lt14s8c+FdA8f2fhnVPF+jzyM8kEGr2shitVlkYM6o6N5YYAAgIyWqXovxcfxWv\/AAdR1rc7ttd\/lL8Nv6sfVHj\/AP4L7+Dm\/YV+M\/xN8N+BPiJofxA+EtzZ6Lc+AfHOhnR9bt9S1Bo49N+0QLI+2CZ5lbIfdsRuASufNfjZ48\/bh\/4Jk\/B+0\/aG+KXxv8D\/ABm8G6bc2cvjz4cWvga20iLw7YXVzEk8mlajEwnuZLUuFT7UFVo97OGcCvJP2Uf+CC\/jvVP2ff2ufhxq3w50n9n2w+LsnhrXfAgsPGL+KbXRbuyU3S20tw7m5keG6CiaR02s0snlGREQn1T42+AP25P+CmPwe0v9nf4pfBPwd8H\/AAbqF3Zw+P8A4k2vjiz1eLxJYWk0bzppunRKZ7aS6aNXT7RuVE3K+0njRpKStvpvtsr\/AI3v5WsTp9rbXbf+rbed7np3xv8A2g\/j7+3b+3N43+CP7PfxO0P4G+Gvg\/o2l6n4p8bXPhSHxLqepahqEbzW2n21rcstutuLfEjyn95vCqvy7s8T+1v+0J+2N+wl\/wAEfPj74m+I\/i7wfc\/Ef4d6lb2\/gvx7o2m2q3HiLT5L21T7Xd6a8UlpBKVldNigjg\/ICiyy9p8bP2evj\/8AsI\/t0eOfjf8As+\/DPQfjp4Z+MGkaVpnibwTceKofDWqaZf6fE8Nvf293cq1u1uYPkeIgPvZCowGI4n9rf9nn9sb9u3\/gkH+0D4b+I\/hPwhb\/ABF+I+p2tx4K+H+jalatP4a0+K7tGNpdak8kdrcS4hklLhsZZsPhkhhh25Xy\/jve\/T+rW8zSFvaR5trr\/g3\/AOD+Rb\/4Kt\/8Fr\/Bnw1\/4Jy6hr3wL\/aJ+E198Xxc6JHa2+i+IdG1rUHEt9bJdhbNjKG\/ctLu\/dnYMkbcZH6VWErTWMLscs6KSfUkV+av\/BVv\/gij4M+JX\/BOXUNB+Bf7O3wmsvi+bnRJLW40Xw9o2i6ggivrZ7sreMIgv7lZd37wbxkDdnB9T8WeBdf\/AGV\/+CkHwi1S6+IvxPvvDfxb1PV9KuYNR8TTarY3moPp813b6YNKIjs9NtLeGyd4ru1R7iRwY5jtdpX0drfN\/krfqYq9l6H25RRRWQwooooAKKKKACiiigAooooA+QPiX+1H478P\/wDC6\/smu+V\/wiP7QHw\/8E6T\/oVu32TR9T\/4Qn7da8xnf5v9r6h+8fdIn2j5HXZHs+v6+APjJ\/zcd\/2dV8Kv\/ecV9\/0AFFFFABRRRQAUUUUAeQf8FCfilr3wO\/YF+OPjbwtf\/wBl+J\/B\/wAP9e1vSLzyY5\/sl5badcTQS+XIrRvtkRW2urKcYIIyKPBXxS17V\/2+viX4JuL\/AMzwz4f+H\/hLW7Cz8mMfZ7y+1HxNDdS+YF8xt8en2a7WYqvk5UKWctz\/APwVi\/5RZftLf9kq8Uf+mi6o+HP\/AClN+Mn\/AGSrwH\/6d\/GdAHv9FFFABRRRQAUUUUAFFFFABRRRQAUUUUAZXjjx1onwx8Ial4h8S6zpXh7QdHga6v8AUtTu47SzsYVGWkllkIREA5LMQBXP\/BH9pT4dftMaJean8OPH\/gr4g6bp0\/2W6u\/DWuWurQW0u0N5bvA7qr7SDtJBwQa8y\/bf\/YE0z9vLxZ8L7Xxnq8V58NPA+ty6\/rvgu4sGns\/GNwsLJZLcOJUAhglYymJ0ljlOFZcCvnT4Nfsy\/DHQP+CyOk6t+zf4Q8NeCdC+HHhfUtC+LNz4UsItN0G+upzC+n6U0UAFvJqELiSeXaokijaISN88aU1Zuzff8v6\/rQbWl0fobRRRSEFFFFABRRRQAUUUUAeAfEb\/AJSm\/Bv\/ALJV48\/9O\/gyj\/gk7\/yiy\/Zp\/wCyVeF\/\/TRa0fEb\/lKb8G\/+yVePP\/Tv4Mo\/4JO\/8osv2af+yVeF\/wD00WtAHv8ARRRQAUUUUAFFFFABRRRQAUUUUAFFFFABRXmHxr\/bd+C\/7Nfiq30L4jfF74YeANbu7Rb+DT\/Eniqx0q7mt2d0WZYp5Udoy8cihwMExsM5U44\/\/h7F+yz\/ANHLfAD\/AMOHpH\/yRQB79LEs8TI6h0cFWVhkMD1BFZXgPwBoXws8I2Hh\/wAMaJpPhzQdLj8qy03S7OOzs7RMk7Y4owEQZJOFAGSa8W\/4exfss\/8ARy3wA\/8ADh6R\/wDJFH\/D2L9ln\/o5b4Af+HD0j\/5IouB7\/RXgH\/D2L9ln\/o5b4Af+HD0j\/wCSKP8Ah7F+yz\/0ct8AP\/Dh6R\/8kUAe\/wBFeAf8PYv2Wf8Ao5b4Af8Ahw9I\/wDkij\/h7F+yz\/0ct8AP\/Dh6R\/8AJFAHv9FeAf8AD2L9ln\/o5b4Af+HD0j\/5Io\/4exfss\/8ARy3wA\/8ADh6R\/wDJFAHv9ePeAP2BfhP8L\/jTceP9E8Ly2viKa8vNRhV9XvrjTNOu7z\/j7u7PT5Jms7O4n+bzZreGOSTzJNzHzH3YP\/D2L9ln\/o5b4Af+HD0j\/wCSKP8Ah7F+yz\/0ct8AP\/Dh6R\/8kU7hc9\/or4Q0b\/g5P\/Y\/l+MureBNb+Kmn+Gdb0\/xAuhWlzcBdR0bWEcRGHUIdU09rmwSzkEwy9xPDJCUkE8cJQivs\/4W\/Fnwt8cfAlh4p8FeJvD\/AIw8M6p5n2PV9E1GHULC78uRopPLnhZo32yI6HaThkYHkEUgOgooooAKKKKACiiigAoorC+KHxK0b4NfDbxB4u8RXi6foPhjTp9V1G5YZEFvDG0kj474VScUN21Y0m3ZHw78ZP8Am47\/ALOq+FX\/ALzivv8Ar8hj8Yv2vPjv8FtT\/aC8H\/s2\/BbV\/g38R\/E+h\/E0+AJ\/EOtyfEbX2099LXT75JoWFjFL5ek6fOsKIU8uEK8UztJ5n62eGtTuNa8O2F7eaddaRd3dvHNNY3LxvNZOygtE7RM8ZZSSpKMykjgkYNOztcVy7RRRSAKKKKACiiigDwD\/AIKxf8osv2lv+yVeKP8A00XVHw5\/5Sm\/GT\/slXgP\/wBO\/jOuB\/4K8ftOS+B\/hfoPwO8OeB9N+JnxD\/aX\/tDwVpHh3U9Um03TfsclnIL+9vZ4SJ1tYIHy4gZZmD4jZWww5b9ijxH+1P4W\/b012w\/aD+EHwvu5\/Gng+zQfEn4YahqI0S0g026vHt9MvLfUpN3neZqV06vAoYiYBhIiFoGtRvTf+uh9zUUUUhBRRRQAUUUUAFFFfAHjv9vD9qD9rT9oL4k+FP2SvCfwPXwp8G9XPhrX\/FXxOvdSaDXtWESSTWmnwWGHT7MW2SSTEq7SLtxtJJfoO3U+\/wCivz2+Lf8AwVP+OXwk\/Y6+A3jLxZ8IdM+GvxC+IXxZ0j4deJNB15nvYI7a4uZYJr2yMMyOgk8vfF52doPKypskf2P\/AIKYftv+LP2M\/FH7O9j4Y0\/w9fxfFv4q6X4G1g6pBNK1tZXUczSSW\/lyx7ZgY12s+9Rk5Q9qUW5KK72\/L\/MGmkm+1\/z\/AMj6moooqRHxl\/wWP1z9py9+HvhPwp+zt8NNZ8a2PiO8k\/4TbUNI8Zab4X1Oz01Ao+x2d1dtugmuS7D7TFG7xJG+3ZI6SJm\/8E4vil8evCGteGvhfrH7DOmfs6\/CbSrOZYtVsPilo+uQ6e6qzqptLaMTSvNITvlLFizs7liST9v0U07aA9QooopAFFFFABRRRQAUUV4B\/wANi3n7Rv8AxL\/2eYfD\/jmFv+Pvx3qL3S+DdNib5BLZXUMZj124STfm1spkiU2lxDcXtjN5KygHxl4L\/Z+8X\/8ABaz9qb4z+Otd+Nvxh+Dnhb4KeLtU+GHgfT\/hpq0GgalGkS2b6ncXl6IpJZ47qeC1cQZVE+zIeSMj7o\/YK+EnxX+Bn7NOjeFvjL8RLH4peM9Ilng\/4SGDTzaSXdmJGFsJ8n97OIgu+TapYnB3sDLJ8xeNv2DP2of2R\/2gPiV4q\/ZL8X\/BGXwr8ZNZbxNr\/hb4n2OorBoGrNGiTXWnz6f8zi4xueOZQEMald25se2fs5\/BP9oT9mf9kLQ9I1L4heH\/AI4\/FiHVJ9U1y58VyTaPp+oJcvK8lja3dvDNLaR28kqNFJJbXO5IGhEUCyxva1F+79339fx\/Ac\/i0+Xp\/X9dT6VorzD4Kfte+DfjZ4quPCsU+oeGPiFp1o17qHgvxJanTNfs4UdIpbhbdzi7s0nfyRf2bT2UsissVxLjNen1IgooooAKKK4\/41\/H7wb+zp4Vt9Z8a+IdP0G0v7tdO0+OZi93rF66O8VjZW6Bpry8lEbiK2t0kmlK7URm4oA8h\/4K2\/tf61+wl\/wT0+JPxM8N2kF54m0ayitdGWdQ0MN7dTx2sE0in7yRyTK5X+IJjvXz54W\/4JIftAfDjXfAvxD8MftnfGrWviUuq2d94xsPGWorqfgnVLaQ51CG00aNES2B3HyUWQCMDarxnbIntnx0+D+pf8FVv2fvHvgDxZ4V1n4d\/CjxZor2On3Gt2iR+JtTvDLFPaatDbCVvsFtCqI6wXqLeySysssFj9lxd+J6B+yf\/wAFB\/Gmt+CfBHjL47\/Bfw78M\/BurWV1d+L\/AAXpeoQ+OPFdrZOGjiuoLgNYxG52L56xkoMlcTRlo3qD97+rW\/rfuOXw\/f8A8D+uh5hqv\/BZL4d\/sCf8Fqf2ovDvx9+L3iHw94Pm0rwsPCOk3MGravp9pL9hZ7w29vbRTJbljJEznam8kcsQcd9\/wRZ\/bxtf29v2+v2yPEnhT4g+IvHPwqg1HwyfCEd7Nex2WnRNp8q3ItrS6CtbB54nLARpvZdxzwa99\/Zr\/Yi8WfBz\/gp3+0b8atU1Hw\/ceFvi\/pvhyz0e1tp5m1C2fTraSKc3CNEsahmcFNkj5GcheleNal\/wS68Pv+2N+0V4l+MOqfCzUdB\/aG8SeH7v4e6Hrl7cXMF3qumaTPEsV\/prPbRagFYPMLQSyq6QlzsZAyum0ou\/b\/25foVVab08vy\/z3P0Kor5e\/wCCN+pW03\/BP\/wrpVompfZ\/CWp6z4ZSW6vjex3IsNVu7TzbZ9q7bNvJzBEBiKHy4wWCbm+oal+RLCiiikIKKK+X\/wBur\/gq\/wCBv2FPiBofgy68GfFn4qePdd0+XWk8L\/Drwy2uapZ6ZGxje\/nQvGkduJMR7t5bcw+XGSBuw7Nn1BRXzn8LP+Cp3wk+M9v8D7zw9qWpXujftBQ33\/CK6obdI7X7XZx+ZLYXG5xJFc4WYBQjKWt5BuB2b+z\/AG5P2x\/DH7AH7LXir4ueMrHXtT8N+EI4Zby20aGKa+lEs8cC+WkskSEhpVJ3OvAPU8Fy03CKcrJdT1mivFf21P27vCP7CX7KV38YfF2neJNR8NWUmnxPbaPbwzX5N7cRW8WElljTAeZS3z8AHG44B9ogmFxAkgziRQwz15FDT3FcdRXwl8Xv+Dg74QfC\/wCJ3irRtM8CfHf4ieFvh\/ftpvi\/x74O8Eyar4T8JzxH\/Sku7wSKw+zJiSUxxuAh+XeeK9f\/AGsP+Cl3gv8AZ0\/YQvfjzoVprHxG8O3Ph6XXtBGh6XqF1baqi2zXEfn3FtaziwhcLhri5RI4ycMQRilfTm6D62Po6iuH\/Zz+PWmftK\/CPSfF+laf4j0u21OJWNtrehX+jXMTlFZgIr2CCV4wWwsoTY4GVJFdxTaadmSndXR5B8NP+CfvwP8Ag\/8AFO58eeHfhN4A07x7earqWty+Kf7Et5tee81Caea8l+3yK1yPMa5nXaJNqxv5ShYwqD1+iikMKKK56X4ueFIPihD4Hk8T+Hk8aXGnNq8WgNqMI1SSyWTy2ultt3mmEOdhkC7Q3Gc8UDOhornovi54Um+KMvgdPE\/h5\/GsGnDWJPD66jCdUjsjJ5YujbbvNEJk+QSFdu7jOeK6CWVYImd2CIgLMzHAUDqSaBC0V5t8F\/2y\/hB+0j4hvtI+HfxW+G3j7VtMh+0Xll4c8TWWq3FpHuC75I4JHZF3ELlgBkgdayfil+2t4W8DeO7\/AMFeHLDxB8UfiPpnl\/bPCXg2CG9v9L8yNZo\/7QnmlisdL8yBmmh\/tG5tvtKxOsHnSAIWB6\/XzB8XPjP4V\/4KK\/B3xp8KvhwniHxn4Z8f+HNT0K7+IWh28L+E9IM9nMkTx6hNIkepBpRJC39li8+zzRslz9nOM9B\/wyb4q\/aC\/wBK+Oni\/wDtnSbj5v8AhXvhV5tM8KxoefIv5si81rCyT28q3Dw6deQlDJpcbjNe\/wBS1dWGpNNNH5UfBz\/got+0f+yT+yR4T\/Z+tf2OvjT4g+P\/AIH0ez8I6bq0OkpcfDi\/eFEht76TWUmVVhaAJK6EJsfMTOhBZfvr4i\/tZR\/ASbR2+IvhLxN4f0O60yG51PxdYQLq3hnQ7xi3m211NCftdtDEkck0l\/dWkFhHEoMlzG5Edeu0Vbk3vuL0M\/wn4s0vx74V0zXdC1PT9a0TWrSK\/wBP1CwuEubS\/t5UDxTRSoSkkboysrqSGBBBINaFeIeLP2RNV8KeKtT8TfB\/x5qHw21vWLuW\/wBQ0e\/tX1\/wdq1xK5aWaXSnmia2kZ5bmdn0y5sTPdTma6N2RsJ4T\/be0rRvFWmeFPivoeofB7xlqt3FpunprcyS6B4ju5HEUUWl6un+i3Mk8ol8izmNvqUkcLSvYwpUge30Vx\/xp\/aF8A\/s2+GINb+Ivjjwf4B0a6uBZw3\/AIj1m20q1lnKswiWSd0UuVViFByQpOODUui\/HfwP4j+EMnxC0\/xn4Uv\/AAFFYzam\/iW21a3l0dLSEM0twbtXMIiQI5Z921QjZIwaAOrrj\/jX8fvBv7OnhW31nxr4h0\/QbS\/u107T45mL3esXro7xWNlboGmvLyURuIra3SSaUrtRGbivMP8AhqHxV+0t\/oHwM0nytJl\/ef8ACy\/FWhzSeFdi\/NiwtPtNpeax5ytA0VzbtHpzwzvNHfTPB9km7D4KfsraV8I\/FVx4p1PxF4w+Ifju8tGsJ\/E3im\/S4u0t2dGaG2toI4bDT43ENsJUsba3FwbSCScTSxiSgD5C\/bzsPib8SPid8CP2pfh78HviBrH\/AAofXdWS+8HajHaWOveKfDuo2KRy6lp9p5zyrMq4aOyuxbXhZWjkt4nwK9F\/Y9\/4KLfFv9tT9qMWGnfs2fE\/4V\/BjSNEmfWNe+KGlt4d1ubVWkX7PDZWe+TzoRGJN75xlxloyipP9j0U07b6\/wBf0\/Ucnc8g+Fv7a3hbxz47sPBXiOw8QfC74j6n5n2Pwl4yghsr\/VPLjaaT+z54ZZbHVPLgVZpv7Oubn7MsqLP5MhKD1+uf+KXwt0L40eBL\/wANeJbH+0NJ1Dy2dFmkt5oJYpFlhuIJomWWC4hmSOWKeJ0lhlijkjdHRWHkH\/CI\/Fn9lP8A0jw9qPiD46eAoP3S+FtRazXxlpit8kQstWubi2tr63hVIlMWpH7Y4kuLh9SuJEjtZUI9\/orgPgX+1H4E\/aP\/ALVh8J679p1fQPK\/tnQ9QsrjSde0Hzt5g+3abdxxXln5yxvJF9ohj82PEibkZWNb4cftkfCH4x\/ErUPBnhH4q\/DfxV4w0gTNfaFo\/iayvtTshDII5TLbxSNIgR2CtuUbWIBwTigD0iiuA+On7UfgT9nD+yofFmu\/Z9X1\/wA3+xtD0+yuNW17XvJ2Gf7DptpHLeXnkrIkkv2eGTyo8yPtRWYef\/8ACI\/Fn9qz\/SPEWo+IPgX4Cn\/dN4W05rNvGWpqvySi91a2uLm2sbeZXlURaaftiCO3uE1K3keS1iAOg+KX7a3hbwN47v8AwV4csPEHxR+I+meX9s8JeDYIb2\/0vzI1mj\/tCeaWKx0vzIGaaH+0bm2+0rE6wedIAh+IPh78VviP\/wAEYfj18dNC1v8AZ++N3xn+Hnxa8dXvxA8I+IPhhoSeIp4ZLyOI3dlqFuJI3tTFIqbJDuEgZtudjV+j3wt+FuhfBfwJYeGvDdj\/AGfpOn+YyI00lxNPLLI0s1xPNKzSz3E0zySyzyu8s0sskkju7sx6Ci76f1\/Vh30sfkz\/AMFJvh58bP8AgpV\/wTo+ANv8W\/gVqWi6x4k+NmjXPiDwhoLXep3GmeGnnuU82+aAb7VltJFEzhxsY7iYWYxR4P7a\/wDwQW+D37IXx3\/ZX8X\/ALOXwW8R6frlr8ZdE\/4SPUNJvdZ10adpCiWSSedZ5p44IUkSImZlUA4BbBIP7CUy4t47u3khmRJYpVKOjqGV1IwQQeoI7VcZcslJLrf8v8hyldJPorfi3+p8W\/s6eDdd\/ZV\/4KYyfD\/VfiH8TfE2i+OfAt5relJ4k8TT+I11y6tL+3+2XsomEcekyxfb44Y7SwhFtLEQ7FXjWMfateQfs7\/sHfCv9lTxFcar4G8NXGmXsln\/AGZbG61m\/wBTj0ey80ymysI7qaVLC0MhDfZ7RYoSUj+T5E2+v1LeiX9bibu7\/wBbBRRRSEFeOftlftu+FP2HtD8C6h4s0\/xDqMPxB8Zab4H05dJghmaG9vnZYZJvNljCwqVO5lLMOMI1ex1+b3\/BzBomseJv2cfgFpvh\/XP+EZ1\/UPjp4XttN1j7Gl7\/AGTcu1wsVz5DkJN5blX8tiFbbg8Ghvb1X5lwSbd+z\/BNn19+1v8Atv8AhT9jPWPhbY+KNP8AEV\/L8W\/Gdn4G0c6XBDKtte3SyNHJceZLHthAjbcyb2GRhD29guLiO0t5JppEiiiUu7uQqooGSST0AHevxd\/4KJ\/sv\/tH\/Aj4\/wD7HmqfGP8Aakb49aDc\/HbQLey0Rfhrpfhc2d1iZhcie1kZpDsV08tsL+83Zyor65+J37UHxT\/bA+F\/7QvwQuvhTH4K8cN8NtRudNbSPF8WvyabPcxTw2thqjQQxx2OozRmKeOCGW5Vo2ZvNG0b6kv3fMt7v8EmKKvJL0\/F2MfxL\/wci\/BDw9qE2rReBvj9rHwitb9dPn+LuneA55vAkbeaIHk+2lxI8aTkxFkhYs6kIHBUn6Y8Xft0eEr7Wh4W+G09t8VfiHd29vNbaLoU7z2emi5hSe2n1e\/hjlh0m1kt3+0JJc4kuIYpfskN5MFgf4q\/ZG\/4K\/fsmfA7\/gjV4As\/HXi\/wa03gvwbZ+H9f+G87W03iOS\/tUS1uLL+yJmWV3a4RuXQRkHeWCZYfpn4Y8QW\/ivw3p+qWi3SWmpW0d1CtzbSWsyo6hlDxSKrxtgjKOoZTkEAginJJLTXzJueHf8ADI2vftFf6R+0FrHh\/wAaaFP+9X4a6dpcbeDbdvvRG9+0o9zrFxAzyKJZzBZyGO3uF023uYY5V9\/ooqACiiigDj\/jX8AfBv7RfhW30bxr4e0\/X7Swu11HT5JlKXej3qI6RX1lcIVms7yISOYrm3eOaItuR1bmvMPtnxl\/Zb\/0jWNS\/wCF6fDy0\/eX1\/8A2atl470eAcyTfZbCAWetYaQt5VrBp88VvbbY4tTupFR\/f6KAPlj9p7\/gsJ8Iv2Z\/AvgnU4ofG\/xH8Q\/Eia4t\/DHg3wX4fm1HxRq0lq5jvY\/sEnlPBLaOsiXEVx5UsMkMsbIJI2QdD+wl\/wAFMfh9+363iXTNA07xt4K8c+CZI08SeCfG2iPoviPQBLuMDz27Fl2SoA6sjuNrru2sdtfL37Rnxn8K\/sW\/8HCnh34gfF3UbLwl4G+InwfPhLwz4r1i4+z6RYanb6lJd3NrLcSYht2kh2MGdlDEKM5YCrH7OPxo8Jftpf8ABwF4l8f\/AAj1PT\/Fvgn4c\/CFPCXibxXo8yXWlahqVzqSXdraRXKEpOY4VkYtGWUEspIK4qoq9ut7\/K1\/8vxQ5K1+lrfO9v8AP8D6g\/4ah8VftLf6B8DNJ8rSZf3n\/Cy\/FWhzSeFdi\/NiwtPtNpeax5ytA0VzbtHpzwzvNHfTPB9km7D4KfsraV8I\/FVx4p1PxF4w+Ifju8tGsJ\/E3im\/S4u0t2dGaG2toI4bDT43ENsJUsba3FwbSCScTSxiSvT6KkQUUUUAFc18Wvgz4P8Aj54KuPDXjvwp4a8a+HLt0lm0rXtMg1KymdGDIzQzKyMVYAgkcEZFdLRQFyj4X8L6b4I8N6fo2i6dY6RpGk28dnY2Nlbpb21nBGoWOKONAFRFUABVAAAAAxV6iim2AUUUUgCvzw\/4LCf8FC\/A\/wCxb8YfD\/hTwVbfCbRf2nfizpB0ay8Z+LZrHSbPwjoYkZmu9Q1Cbaxt0kWRorUMfMlQ4RiAr\/ofXlfxj\/YU+CP7RPi8eIfiD8HPhX4618QJajUvEPhOw1S8EKElY\/NniZ9ilmIXOBuPrQVF21PzT\/aJ+Cvw8\/Zl\/wCCev7DXhv4OeONF+Jdl4c+PnhxLHxRo97BfW+u3811dnUplkhlZFDSSXOUVn2Y2HOCa+kv+DmD\/lCR8cP+vTTv\/TpaV7F43\/4Js+Ctd+JPwOuPD9h4Z8FfD34Ia1feJrHwZofh6CysbzVJoJIoLkGFkSHyWnuJdoibzJJAxK7fm9v+Jnwt8MfGrwRfeGfGXhzQvFvhvVAq3mlazp8V\/Y3YVw6iSGVWRwGVWG4HBUHqKc3eLXd3\/Bf5FQqcs4yfT8dWz8Tf+Czf7IP7U3wt\/wCCWWoeIviR+2H\/AMLU8CQXnh77R4R\/4VRpGh\/ad+o2iw\/6bBIZV8p2R+B8+zB4Jr9EP2qv2i\/jf8Evjr4M0u1j+GDfDrx7rFl4Y062mt9Rh1Mie3ZZ7yfWHkjsLKZJ3iWCxMM0t3tZY5A5Kx\/TnxH+DvhH4xeBZPC\/i7wr4c8VeGpTEz6RrGmQ31g5idXiJhlVkJR1Vl4+UqCMECvFPj9+xN4y\/aM+JdtbeIfipFcfCGHxHo\/ikeE\/+EXhTVLW60yaK5gt7fVI5kVbN7q3hmkSa1mmP7xFuERlCW5JpRfe\/wAnb\/Izjp9x8Tf8Ea\/+CkXwF\/Yg\/wCCUq\/Dr4u+N\/C\/w4+Ifwam1rTPGPhTXr6O21u7vEup7iR7e0kInvPPWVSpiV9zMU6givoL\/ghD8BHg\/wCCNPgDwp4+8J240XxXb6rff8I1rVnHcQrpGoX9zcW9tPC4ZXRraaPKOOQ2COor6b+I37GPwe+MPxKsvGni74UfDXxT4x0zyfsmu6v4Ysr7U7XyXLw+XcSxNInluSy4YbScjBr0qpcr3b3f3fd\/Vht9Ft\/X9eZFYWEGlWMFrawxW1tbRrFDDEgSOJFGFVVHAAAAAHAAqWiipbEFFFFABX5P\/t7fF\/4p\/BP\/AIOJfBesfCH4Pf8AC7\/FUnwLuLaTw9\/wldp4a8q2bWSXuftN0rRnYyxr5YG5vMyOFNfrBXjmofsR+FNS\/bw079oaTUPEI8aaZ4Nl8DxWSzwjS2spLsXTSNH5XmmbeMBhKF28bM80dV\/XQtSSjJd\/80\/0PzR+AX7XXxRh\/wCC7nxD8f8Axg\/Z68XfD\/xb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alt=\"\" \/><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"size-full wp-image-2481 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07202704\/ex.jpeg\" alt=\"\" width=\"625\" height=\"120\" \/><\/p>\n<\/div>\n<h3><span style=\"color: #6c64ad;font-size: 1em;font-weight: 600\">Claisen condensation mechanism<\/span><\/h3>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_2\" class=\"mt-section\">\n<p>1) Enolate formation<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"size-full wp-image-2484 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07202926\/download-6.jpeg\" alt=\"\" width=\"799\" height=\"147\" \/><\/p>\n<p>2) Nucleophilic attack<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone size-full wp-image-2480\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07202700\/21.jpeg\" alt=\"\" width=\"538\" height=\"248\" \/><\/p>\n<p>3) Removal of leaving group<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone size-full wp-image-2479\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07202655\/3.jpeg\" alt=\"\" width=\"599\" height=\"159\" \/><\/p>\n<\/div>\n<div id=\"section_3\" class=\"mt-section\">\n<h3 class=\"editable\">Dieckmann Condensation<\/h3>\n<p>A diester can undergo an intramolecular reaction called a Dieckmann condensation.<\/p>\n<div>\n<div class=\"textbox examples\">\n<h3>Example: Dieckman Condensation<\/h3>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"size-full wp-image-2485 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07203054\/downex.jpeg\" alt=\"\" width=\"582\" height=\"186\" \/><\/p>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_4\" class=\"mt-section\">\n<h3 class=\"editable\">Crossed Claisen condensation<\/h3>\n<p>Claisen condensations between different ester reactants are called <strong>Crossed<\/strong> <strong>Claisen <\/strong>reactions. Crossed Claisen reactions in which both reactants can serve as donors and acceptors generally give complex mixtures. Because of this most Crossed Claisen reactions are usually not performed unless one reactant has no alpha hydrogens.<\/p>\n<div>\n<div class=\"textbox examples\">\n<h3 class=\"boxtitle\">Example : Crossed Claisen Condensation<\/h3>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"size-full wp-image-2486 aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/07203139\/download-7.jpeg\" alt=\"\" width=\"625\" height=\"102\" \/><\/p>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_5\" class=\"mt-section\">\n<h3 class=\"editable\">Contributors<\/h3>\n<ul>\n<li>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/li>\n<\/ul>\n<\/div>\n<\/section>\n<\/div>\n<\/div>\n<\/div>\n<\/section>\n<\/div>\n<\/section>\n<\/div>\n<\/section>\n<\/div>\n<\/section>\n<\/div>\n<\/section>\n<\/div>\n<\/div>\n<\/section>\n<\/div>\n<\/section>\n<\/div>\n<\/section>\n<\/div>\n<\/section>\n<\/div>\n<\/section>\n<\/div>\n<\/section>\n<\/article>\n\n\t\t\t <section class=\"citations-section\" role=\"contentinfo\">\n\t\t\t <h3>Candela Citations<\/h3>\n\t\t\t\t\t <div>\n\t\t\t\t\t\t <div id=\"citation-list-1924\">\n\t\t\t\t\t\t\t <div class=\"licensing\"><div class=\"license-attribution-dropdown-subheading\">CC licensed content, Shared previously<\/div><ul class=\"citation-list\"><li>Transesterification. <strong>Authored by<\/strong>: Prof. Steven Farmer and Gamini Gunawardena. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Esters\/Reactivity_of_Esters\/Transesterification\">https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Esters\/Reactivity_of_Esters\/Transesterification<\/a>. <strong>Project<\/strong>: Chemistry LibreTexts. <strong>License<\/strong>: <em><a target=\"_blank\" rel=\"license\" href=\"https:\/\/creativecommons.org\/licenses\/by-nc-sa\/4.0\/\">CC BY-NC-SA: Attribution-NonCommercial-ShareAlike<\/a><\/em><\/li><li>Saponification. <strong>Authored by<\/strong>: Prof. Steve Farmer. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Esters\/Reactivity_of_Esters\/Saponification\">https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Esters\/Reactivity_of_Esters\/Saponification<\/a>. <strong>Project<\/strong>: Chemistry LibreTexts. <strong>License<\/strong>: <em><a target=\"_blank\" rel=\"license\" href=\"https:\/\/creativecommons.org\/licenses\/by-nc-sa\/4.0\/\">CC BY-NC-SA: Attribution-NonCommercial-ShareAlike<\/a><\/em><\/li><li>Organic Chemistry With a Biological Emphasis. <strong>Authored by<\/strong>: u00a0Tim Soderberg. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\">https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)<\/a>. 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