{"id":2131,"date":"2018-11-30T16:10:37","date_gmt":"2018-11-30T16:10:37","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/?post_type=chapter&#038;p=2131"},"modified":"2019-01-09T09:49:49","modified_gmt":"2019-01-09T09:49:49","slug":"22-3-reaction-of-acyl-derivatives-with-weak-nucleophiles","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/22-3-reaction-of-acyl-derivatives-with-weak-nucleophiles\/","title":{"raw":"22.3. Reaction of acyl derivatives with weak nucleophiles","rendered":"22.3. Reaction of acyl derivatives with weak nucleophiles"},"content":{"raw":"<article id=\"elm-main-content\" class=\"elm-content-container\"><section class=\"mt-content-container\">\r\n<div id=\"section_4\" class=\"mt-section\"><header>\r\n<h2>Introduction<\/h2>\r\nAs we saw with aldehydes and ketones in <a href=\"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/21-2-general-mechanism\/\">section 21.2<\/a>, weak nucleophiles such as alcohols and water do not directly add to an unactivated carbonyl group; instead, the C=O must first be activated using acid.\u00a0 The same applies with carboxylic acid derivatives, so there are several acyl substitution reactions that involve acid catalysis.\u00a0 This type of mechanism is best exemplified by Fischer esterification, which involves the acid catalyzed reaction between an activated (protonated) form of a carboxylic acid and and alcohol (as weak nucleophile) to form an ester.\r\n<h2 id=\"title\">Preparation of esters by Fischer esterification<\/h2>\r\n<div class=\"textbox learning-objectives\">\r\n<h3>Learning Objectives<\/h3>\r\n<header><strong>Skills to Develop<\/strong>\r\n<dl class=\"mt-last-updated-container\"><\/dl>\r\n<\/header><section class=\"mt-content-container\">\r\n<div id=\"skills\">\r\n<ul>\r\n \t<li>To identify and describe the substances from which most esters are prepared.<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/section><\/div>\r\n<\/header><section class=\"mt-content-container\">Some esters can be prepared by Fischer <span class=\"margin_term\"><a class=\"glossterm\">esterification<\/a><\/span>, a reaction in which a carboxylic acid and an alcohol, heated in the presence of a mineral acid catalyst, form an ester and water:\r\n<div><img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30160353\/esterification.jpg\" alt=\"esterification.jpg\" width=\"794\" height=\"92\" \/><\/div>\r\nThe reaction is reversible. As a specific example of an esterification reaction, butyl acetate can be made from acetic acid and 1-butanol.\r\n<div id=\"fwk-gob-eq15_004\"><img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30160357\/butyl_acetate.jpg\" alt=\"butyl acetate.jpg\" width=\"604\" height=\"99\" \/><\/div>\r\n<div id=\"note\">\r\n<div class=\"textbox\">\r\n<div id=\"note\">\r\n<h3 class=\"boxtitle\">A Closer Look: Condensation Polymers<\/h3>\r\n<p id=\"gob-ch15_s08_p03\" class=\"para\">A commercially important esterification reaction is condensation polymerization, in which a reaction occurs between a dicarboxylic acid and a dihydric alcohol (diol), with the elimination of water. Such a reaction yields an ester that contains a free (unreacted) carboxyl group at one end and a free alcohol group at the other end. Further condensation reactions then occur, producing polyester polymers.<\/p>\r\n<p id=\"gob-ch15_s08_p04\" class=\"para\">The most important polyester, polyethylene terephthalate (PET), is made from terephthalic acid and ethylene glycol monomers:<\/p>\r\n\r\n<div id=\"fwk-gob-eq15_005\" class=\"informalfigure large\"><img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30160401\/PET.jpg\" alt=\"PET.jpg\" width=\"574\" height=\"274\" \/><\/div>\r\n<p id=\"gob-ch15_s08_p05\" class=\"para\">Polyester molecules make excellent fibers and are used in many fabrics. A knitted polyester tube, which is biologically inert, can be used in surgery to repair or replace diseased sections of blood vessels. PET is used to make bottles for soda pop and other beverages. It is also formed into films called Mylar. When magnetically coated, Mylar tape is used in audio- and videocassettes. Synthetic arteries can be made from PET, polytetrafluoroethylene, and other polymers.<\/p>\r\n\r\n<\/div>\r\n<div id=\"section_1\" class=\"mt-section\">\r\n\r\n&nbsp;\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_1\" class=\"mt-section\">\r\n<h3 class=\"editable\">Summary<\/h3>\r\nEsters are made by the reaction of a carboxylic acid with an alcohol, a process that is called esterification.\r\n<div id=\"section_15\">\r\n<div id=\"section_1\" class=\"mt-section\">\r\n<h3 class=\"editable\">Synthesis of \u2018banana oil\u2019<\/h3>\r\nMany esters can be synthesized simply by mixing together a carboxylic acid and an alcohol, along with a catalytic amount of sulfuric acid.\u00a0 A popular reaction in undergraduate organic lab courses is the preparation of isopentyl acetate (also called \u2018banana oil\u2019 because it is a flavor component in bananas) from acetic acid and isopentyl alcohol.\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\/30160702\/image091.png\" alt=\"image090.png\" width=\"560\" height=\"65\" \/>\r\n\r\nNotice the double arrows in the above figure: because esters and carboxylic acids are of approximately the same stability, this esterification reaction is highly reversible.\r\n\r\nThe main role of the acid catalyst in this reaction is to protonate the carboxylic acid, thus making the carbonyl carbon more electrophilic.\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\/30160706\/image093.png\" alt=\"image092.png\" width=\"561\" height=\"373\" \/>\r\n<div class=\"textbox exercises\">\r\n<h3>Exercises<\/h3>\r\n<a class=\"mt-disabled\" rel=\"broken\">Template:ExampleStart<\/a>\r\n\r\n<u>Exercise 12.4<\/u>: In the synthesis of isopentyl acetate, an excess of acetic acid is used, usually about three molar equivalents relative to the amount of isopentyl alcohol.\u00a0 What is the reason for this?\r\n\r\n<u>Exercise 12.5<\/u>: Could a similar esterification reaction occur with the addition of a small amount of NaOH instead of H<sub>2<\/sub>SO<sub>4<\/sub>? Explain.\r\n\r\n<u>Exercise 12.6<\/u>: Draw a complete mechanism for the exact reverse of the acid-catalyzed esterification shown above.\u00a0 What would you call this reaction in organic chemistry terms?\r\n\r\n<a title=\"Organic Chemistry\/Organic Chemistry With a Biological Emphasis\/Solution Manual\/Chapter 12 Solutions\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\/Solution_Manual\/Chapter_12_Solutions\" rel=\"internal\">Solutions<\/a>\r\n\r\n<a class=\"mt-disabled\" rel=\"broken\">Template:ExampleEnd<\/a>\r\n\r\n<\/div>\r\nMany other fragrant esters can be synthesized in similar reactions.\u00a0 A few examples of esters found in foods are given below.\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\/30160710\/image095.png\" alt=\"image094.png\" width=\"559\" height=\"334\" \/>\r\n<div class=\"textbox exercises\">\r\n<h3>Exercises<\/h3>\r\n<a class=\"mt-disabled\" rel=\"broken\">Template:ExampleStart<\/a>\r\n\r\n<u>Exercise 12.7<\/u>: For each fragrant ester shown above, provide the carboxylic acid and alcohol starting materials needed.\r\n\r\n<a title=\"Organic Chemistry\/Organic Chemistry With a Biological Emphasis\/Solution Manual\/Chapter 12 Solutions\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\/Solution_Manual\/Chapter_12_Solutions\" rel=\"internal\">Solution<\/a>\r\n\r\n<a class=\"mt-disabled\" rel=\"broken\">Template:ExampleEnd<\/a>\r\n\r\n&nbsp;\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_16\">\r\n<div id=\"section_2\" class=\"mt-section\"><\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_2\" class=\"mt-section\">\r\n<div class=\"textbox exercises\">\r\n<div id=\"section_2\" class=\"mt-section\">\r\n<h3 class=\"editable\">Concept Review Exercises<\/h3>\r\n<div class=\"question qandaentry\">\r\n<ol>\r\n \t<li id=\"gob-ch15_s08_qs01_p01\" class=\"para\">From what carboxylic acid and what alcohol can the ester isopropyl nonanoate be made?<\/li>\r\n \t<li class=\"para\">From what carboxylic acid and what alcohol can the ester cyclobutyl butyrate be made?<\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_3\" class=\"mt-section\">\r\n\r\n&nbsp;\r\n<h3 class=\"editable\">Answers<\/h3>\r\n[reveal-answer q=\"544827\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"544827\"]\r\n<div class=\"answer qandaentry\">\r\n<ol>\r\n \t<li id=\"gob-ch15_s08_qs01_p02_ans\" class=\"para\">nonanoic acid and isopropyl alcohol<\/li>\r\n \t<li class=\"para\">butyric acid and cyclobutyl alcohol[\/hidden-answer]<\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_4\" class=\"mt-section\">\r\n\r\n&nbsp;\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_5\" class=\"mt-section\">\r\n<div class=\"textbox exercises\">\r\n<h3>Exercises<\/h3>\r\n<div id=\"section_4\" class=\"mt-section\">\r\n<ol id=\"gob-ch15_s08_qs02_qd01\" class=\"qandadiv\">\r\n \t<li id=\"gob-ch15_s08_qs02_qd01_qa01\" class=\"qandaentry\">\r\n<div class=\"question\">\r\n<p id=\"gob-ch15_s08_qs02_p01\" class=\"para\">Write the equation for the reaction of acetic acid with each compound.<\/p>\r\n\r\n<ol id=\"gob-ch15_s08_qs02_l01\" class=\"orderedlist\" start=\"1\">\r\n \t<li>ethanol<\/li>\r\n \t<li>1-butanol in the presence of a mineral acid catalyst<\/li>\r\n<\/ol>\r\n<\/div><\/li>\r\n \t<li id=\"gob-ch15_s08_qs02_qd01_qa02\" class=\"qandaentry\">\r\n<div class=\"question\">\r\n<p id=\"gob-ch15_s08_qs02_p02\" class=\"para\">Write the equation for the reaction of benzoic acid with each compound.<\/p>\r\n\r\n<ol id=\"gob-ch15_s08_qs02_l03\" class=\"orderedlist\" start=\"1\">\r\n \t<li>methanol<\/li>\r\n \t<li>1-propanol in the presence of a mineral acid catalyst<\/li>\r\n<\/ol>\r\n<\/div><\/li>\r\n<\/ol>\r\n<\/div>\r\n<div id=\"section_5\" class=\"mt-section\">\r\n\r\n&nbsp;\r\n<h3 class=\"editable\">Answer<\/h3>\r\n[reveal-answer q=\"460266\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"460266\"]\r\n<ol class=\"qandadiv\">\r\n \t<li id=\"gob-ch15_s08_qs02_qd01_qa01_ans\" class=\"qandaentry\">\r\n<div class=\"answer\">\r\n<ol id=\"gob-ch15_s08_qs02_l02_ans\" class=\"orderedlist\" start=\"1\">\r\n \t<li>\r\n<div class=\"informalfigure large\"><img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30160405\/1a.jpg\" alt=\"1a.jpg\" width=\"600\" height=\"217\" \/><\/div><\/li>\r\n \t<li>\r\n<div class=\"informalfigure large\"><img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30160409\/1b.jpg\" alt=\"1b.jpg\" width=\"600px\" height=\"220px\" \/>[\/hidden-answer]<\/div><\/li>\r\n<\/ol>\r\n<\/div>\r\n&nbsp;<\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n&nbsp;\r\n\r\n<header>\r\n<h2 id=\"title\">Preparation of acyl chlorides<\/h2>\r\n<dl class=\"mt-last-updated-container\"><\/dl>\r\n<\/header><section class=\"mt-content-container\">This page discusses the methods\u00a0of swapping the -OH group in the -COOH group of a carboxylic acid for a chlorine atom to make acyl chlorides (acid chlorides) using thionyl<span class=\"mt-color-000000\"> chloride.<\/span> In the examples below, consider the conversion of acetic acid to acetyl chloride to be typical of these types of reactions.\r\n<div id=\"section_3\" class=\"mt-section\">\r\n\r\n<span class=\"mt-color-000000\">T<\/span>hionyl<span class=\"mt-color-000000\"> chloride is a liquid at room temperature and has the formul<\/span>a $$SOCl_2$$.\u00a0 It <span class=\"mt-color-000000\">reacts with carboxylic acids to produce an <\/span>acyl<span class=\"mt-color-000000\"> chloride, giving off\u00a0<\/span>sulfur<span class=\"mt-color-000000\"> dioxide and hydrogen chloride gases.\u00a0<\/span><span class=\"mt-color-000000\">For example:<\/span>\r\n<p style=\"text-align: center\">\\[ CH_3COOH\u00a0+ SOCl_2\u00a0\\rightarrow\u00a0CH_3COCl +SO_2 + \u00a0HCl\\]<\/p>\r\n<img class=\"internal aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30160533\/OrganicCore_AcidHalides59.png\" alt=\"\" width=\"417px\" height=\"58px\" \/>\r\n\r\n<span class=\"mt-color-000000\">The separation is simplified to an extent because the by-products are both gases. Fractional distillation is still required to separate the <\/span>acyl<span class=\"mt-color-000000\"> chloride from any excess acid or <\/span>thionyl chloride<span class=\"mt-color-000000\">.<\/span>\r\n\r\n<\/div>\r\n<div id=\"section_4\" class=\"mt-section\">\r\n<h3 class=\"editable\"><span class=\"mt-color-000000\">Contributors<\/span><\/h3>\r\nJim 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>)\r\n<h3>Video<\/h3>\r\nhttps:\/\/www.youtube.com\/watch?v=SRPQ62dR6b4\r\n\r\n<img class=\"alignnone size-thumbnail wp-image-3020\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/08175258\/frame-44-150x150.png\" alt=\"\" width=\"150\" height=\"150\" \/>\r\n\r\n<section class=\"mt-content-container\">\r\n<div class=\"mt-section\"><header>\r\n<h2 id=\"title\">Hydrolysis of Amides<\/h2>\r\n<\/header><section class=\"mt-content-container\">Generally, amides can be hydrolyzed in either acidic or basic solution. The mechanisms are much like those of ester hydrolysis (<a title=\"18.7: Reactions at the Carbonyl Carbon of Acid Derivatives\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Book%3A_Basic_Principles_of_Organic_Chemistry_(Roberts_and_Caserio)\/18%3A_Carboxylic_Acids_and_Their_Derivatives\/18.07%3A_Reactions_at_the_Carbonyl_Carbon_of_Acid_Derivatives#18-7A_Displacement_Reactions\" rel=\"internal\">Section 18-7A<\/a>), but the reactions are very much slower, a property of great biological importance (which we will discuss later):<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30160902\/Roberts_and_Caserio_Screenshot_24-4-1.png\" alt=\"\" width=\"349px\" height=\"79px\" \/>Amide hydrolysis can be an important route to amines. Hydrolysis under acidic conditions requires strong acids such as sulfuric or hydrochloric, and temperatures of about $$100^\\text{o}$$ for several hours. The mechanism involves protonation of the amide on oxygen followed by attack of water on the carbonyl carbon. The tetrahedral intermediate formed dissociates ultimately to the carboxylic acid and the ammonium salt:<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30160905\/Roberts_and_Caserio_Screenshot_24-4-2.png\" alt=\"\" width=\"408px\" height=\"200px\" \/>A brief summary of important amide reactions follows:<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30160913\/Roberts_and_Caserio_Screenshot_24-4-6.png\" alt=\"\" width=\"517px\" height=\"198px\" \/>\r\n<div id=\"section_1\" class=\"mt-section\">\r\n<h3 class=\"editable\">Contributors<\/h3>\r\n<ul>\r\n \t<li><span class=\"person_name\">John D. Robert <\/span>and <span class=\"person_name\">Marjorie C.<\/span> <span class=\"person_name\">Caserio <\/span>(1977) <em>Basic Principles of Organic Chemistry, second edition.<\/em> W. A. Benjamin, Inc. , Menlo Park, CA. ISBN 0-8053-8329-8. This content is copyrighted under the following conditions, \"You are granted permission for individual, educational, research and non-commercial reproduction, distribution, display and performance of this work in any format.\"<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/section><\/div>\r\n<\/section><\/div>\r\n<\/section><\/div>\r\n<\/section><\/div>\r\n<\/section><\/article>","rendered":"<article id=\"elm-main-content\" class=\"elm-content-container\">\n<section class=\"mt-content-container\">\n<div id=\"section_4\" class=\"mt-section\">\n<header>\n<h2>Introduction<\/h2>\n<p>As we saw with aldehydes and ketones in <a href=\"https:\/\/courses.lumenlearning.com\/suny-potsdam-organicchemistry2\/chapter\/21-2-general-mechanism\/\">section 21.2<\/a>, weak nucleophiles such as alcohols and water do not directly add to an unactivated carbonyl group; instead, the C=O must first be activated using acid.\u00a0 The same applies with carboxylic acid derivatives, so there are several acyl substitution reactions that involve acid catalysis.\u00a0 This type of mechanism is best exemplified by Fischer esterification, which involves the acid catalyzed reaction between an activated (protonated) form of a carboxylic acid and and alcohol (as weak nucleophile) to form an ester.<\/p>\n<h2 id=\"title\">Preparation of esters by Fischer esterification<\/h2>\n<div class=\"textbox learning-objectives\">\n<h3>Learning Objectives<\/h3>\n<\/div>\n<\/header>\n<header><strong>Skills to Develop<\/strong><\/p>\n<dl class=\"mt-last-updated-container\"><\/dl>\n<\/header>\n<section class=\"mt-content-container\">\n<div id=\"skills\">\n<ul>\n<li>To identify and describe the substances from which most esters are prepared.<\/li>\n<\/ul>\n<\/div>\n<\/section>\n<\/div>\n<section class=\"mt-content-container\">Some esters can be prepared by Fischer <span class=\"margin_term\"><a class=\"glossterm\">esterification<\/a><\/span>, a reaction in which a carboxylic acid and an alcohol, heated in the presence of a mineral acid catalyst, form an ester and water:<\/p>\n<div><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\/30160353\/esterification.jpg\" alt=\"esterification.jpg\" width=\"794\" height=\"92\" \/><\/div>\n<p>The reaction is reversible. As a specific example of an esterification reaction, butyl acetate can be made from acetic acid and 1-butanol.<\/p>\n<div id=\"fwk-gob-eq15_004\"><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\/30160357\/butyl_acetate.jpg\" alt=\"butyl acetate.jpg\" width=\"604\" height=\"99\" \/><\/div>\n<div id=\"note\">\n<div class=\"textbox\">\n<div id=\"note\">\n<h3 class=\"boxtitle\">A Closer Look: Condensation Polymers<\/h3>\n<p id=\"gob-ch15_s08_p03\" class=\"para\">A commercially important esterification reaction is condensation polymerization, in which a reaction occurs between a dicarboxylic acid and a dihydric alcohol (diol), with the elimination of water. Such a reaction yields an ester that contains a free (unreacted) carboxyl group at one end and a free alcohol group at the other end. Further condensation reactions then occur, producing polyester polymers.<\/p>\n<p id=\"gob-ch15_s08_p04\" class=\"para\">The most important polyester, polyethylene terephthalate (PET), is made from terephthalic acid and ethylene glycol monomers:<\/p>\n<div id=\"fwk-gob-eq15_005\" class=\"informalfigure large\"><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\/30160401\/PET.jpg\" alt=\"PET.jpg\" width=\"574\" height=\"274\" \/><\/div>\n<p id=\"gob-ch15_s08_p05\" class=\"para\">Polyester molecules make excellent fibers and are used in many fabrics. A knitted polyester tube, which is biologically inert, can be used in surgery to repair or replace diseased sections of blood vessels. PET is used to make bottles for soda pop and other beverages. It is also formed into films called Mylar. When magnetically coated, Mylar tape is used in audio- and videocassettes. Synthetic arteries can be made from PET, polytetrafluoroethylene, and other polymers.<\/p>\n<\/div>\n<div id=\"section_1\" class=\"mt-section\">\n<p>&nbsp;<\/p>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_1\" class=\"mt-section\">\n<h3 class=\"editable\">Summary<\/h3>\n<p>Esters are made by the reaction of a carboxylic acid with an alcohol, a process that is called esterification.<\/p>\n<div id=\"section_15\">\n<div id=\"section_1\" class=\"mt-section\">\n<h3 class=\"editable\">Synthesis of \u2018banana oil\u2019<\/h3>\n<p>Many esters can be synthesized simply by mixing together a carboxylic acid and an alcohol, along with a catalytic amount of sulfuric acid.\u00a0 A popular reaction in undergraduate organic lab courses is the preparation of isopentyl acetate (also called \u2018banana oil\u2019 because it is a flavor component in bananas) from acetic acid and isopentyl alcohol.<\/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\/30160702\/image091.png\" alt=\"image090.png\" width=\"560\" height=\"65\" \/><\/p>\n<p>Notice the double arrows in the above figure: because esters and carboxylic acids are of approximately the same stability, this esterification reaction is highly reversible.<\/p>\n<p>The main role of the acid catalyst in this reaction is to protonate the carboxylic acid, thus making the carbonyl carbon more electrophilic.<\/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\/30160706\/image093.png\" alt=\"image092.png\" width=\"561\" height=\"373\" \/><\/p>\n<div class=\"textbox exercises\">\n<h3>Exercises<\/h3>\n<p><a class=\"mt-disabled\" rel=\"broken\">Template:ExampleStart<\/a><\/p>\n<p><u>Exercise 12.4<\/u>: In the synthesis of isopentyl acetate, an excess of acetic acid is used, usually about three molar equivalents relative to the amount of isopentyl alcohol.\u00a0 What is the reason for this?<\/p>\n<p><u>Exercise 12.5<\/u>: Could a similar esterification reaction occur with the addition of a small amount of NaOH instead of H<sub>2<\/sub>SO<sub>4<\/sub>? Explain.<\/p>\n<p><u>Exercise 12.6<\/u>: Draw a complete mechanism for the exact reverse of the acid-catalyzed esterification shown above.\u00a0 What would you call this reaction in organic chemistry terms?<\/p>\n<p><a title=\"Organic Chemistry\/Organic Chemistry With a Biological Emphasis\/Solution Manual\/Chapter 12 Solutions\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\/Solution_Manual\/Chapter_12_Solutions\" rel=\"internal\">Solutions<\/a><\/p>\n<p><a class=\"mt-disabled\" rel=\"broken\">Template:ExampleEnd<\/a><\/p>\n<\/div>\n<p>Many other fragrant esters can be synthesized in similar reactions.\u00a0 A few examples of esters found in foods are given below.<\/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\/30160710\/image095.png\" alt=\"image094.png\" width=\"559\" height=\"334\" \/><\/p>\n<div class=\"textbox exercises\">\n<h3>Exercises<\/h3>\n<p><a class=\"mt-disabled\" rel=\"broken\">Template:ExampleStart<\/a><\/p>\n<p><u>Exercise 12.7<\/u>: For each fragrant ester shown above, provide the carboxylic acid and alcohol starting materials needed.<\/p>\n<p><a title=\"Organic Chemistry\/Organic Chemistry With a Biological Emphasis\/Solution Manual\/Chapter 12 Solutions\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\/Solution_Manual\/Chapter_12_Solutions\" rel=\"internal\">Solution<\/a><\/p>\n<p><a class=\"mt-disabled\" rel=\"broken\">Template:ExampleEnd<\/a><\/p>\n<p>&nbsp;<\/p>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_16\">\n<div id=\"section_2\" class=\"mt-section\"><\/div>\n<\/div>\n<\/div>\n<div id=\"section_2\" class=\"mt-section\">\n<div class=\"textbox exercises\">\n<div id=\"section_2\" class=\"mt-section\">\n<h3 class=\"editable\">Concept Review Exercises<\/h3>\n<div class=\"question qandaentry\">\n<ol>\n<li id=\"gob-ch15_s08_qs01_p01\" class=\"para\">From what carboxylic acid and what alcohol can the ester isopropyl nonanoate be made?<\/li>\n<li class=\"para\">From what carboxylic acid and what alcohol can the ester cyclobutyl butyrate be made?<\/li>\n<\/ol>\n<\/div>\n<\/div>\n<div id=\"section_3\" class=\"mt-section\">\n<p>&nbsp;<\/p>\n<h3 class=\"editable\">Answers<\/h3>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q544827\">Show Answer<\/span><\/p>\n<div id=\"q544827\" class=\"hidden-answer\" style=\"display: none\">\n<div class=\"answer qandaentry\">\n<ol>\n<li id=\"gob-ch15_s08_qs01_p02_ans\" class=\"para\">nonanoic acid and isopropyl alcohol<\/li>\n<li class=\"para\">butyric acid and cyclobutyl alcohol<\/div>\n<\/div>\n<\/li>\n<\/ol>\n<\/div>\n<\/div>\n<div id=\"section_4\" class=\"mt-section\">\n<p>&nbsp;<\/p>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_5\" class=\"mt-section\">\n<div class=\"textbox exercises\">\n<h3>Exercises<\/h3>\n<div id=\"section_4\" class=\"mt-section\">\n<ol id=\"gob-ch15_s08_qs02_qd01\" class=\"qandadiv\">\n<li id=\"gob-ch15_s08_qs02_qd01_qa01\" class=\"qandaentry\">\n<div class=\"question\">\n<p id=\"gob-ch15_s08_qs02_p01\" class=\"para\">Write the equation for the reaction of acetic acid with each compound.<\/p>\n<ol id=\"gob-ch15_s08_qs02_l01\" class=\"orderedlist\" start=\"1\">\n<li>ethanol<\/li>\n<li>1-butanol in the presence of a mineral acid catalyst<\/li>\n<\/ol>\n<\/div>\n<\/li>\n<li id=\"gob-ch15_s08_qs02_qd01_qa02\" class=\"qandaentry\">\n<div class=\"question\">\n<p id=\"gob-ch15_s08_qs02_p02\" class=\"para\">Write the equation for the reaction of benzoic acid with each compound.<\/p>\n<ol id=\"gob-ch15_s08_qs02_l03\" class=\"orderedlist\" start=\"1\">\n<li>methanol<\/li>\n<li>1-propanol in the presence of a mineral acid catalyst<\/li>\n<\/ol>\n<\/div>\n<\/li>\n<\/ol>\n<\/div>\n<div id=\"section_5\" class=\"mt-section\">\n<p>&nbsp;<\/p>\n<h3 class=\"editable\">Answer<\/h3>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q460266\">Show Answer<\/span><\/p>\n<div id=\"q460266\" class=\"hidden-answer\" style=\"display: none\">\n<ol class=\"qandadiv\">\n<li id=\"gob-ch15_s08_qs02_qd01_qa01_ans\" class=\"qandaentry\">\n<div class=\"answer\">\n<ol id=\"gob-ch15_s08_qs02_l02_ans\" class=\"orderedlist\" start=\"1\">\n<li>\n<div class=\"informalfigure large\"><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30160405\/1a.jpg\" alt=\"1a.jpg\" width=\"600\" height=\"217\" \/><\/div>\n<\/li>\n<li>\n<div class=\"informalfigure large\"><img decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30160409\/1b.jpg\" alt=\"1b.jpg\" width=\"600px\" height=\"220px\" \/><\/div>\n<\/div>\n<\/div>\n<\/li>\n<\/ol>\n<\/div>\n<p>&nbsp;<\/li>\n<\/ol>\n<\/div>\n<\/div>\n<p>&nbsp;<\/p>\n<header>\n<h2 id=\"title\">Preparation of acyl chlorides<\/h2>\n<dl class=\"mt-last-updated-container\"><\/dl>\n<\/header>\n<section class=\"mt-content-container\">This page discusses the methods\u00a0of swapping the -OH group in the -COOH group of a carboxylic acid for a chlorine atom to make acyl chlorides (acid chlorides) using thionyl<span class=\"mt-color-000000\"> chloride.<\/span> In the examples below, consider the conversion of acetic acid to acetyl chloride to be typical of these types of reactions.<\/p>\n<div id=\"section_3\" class=\"mt-section\">\n<p><span class=\"mt-color-000000\">T<\/span>hionyl<span class=\"mt-color-000000\"> chloride is a liquid at room temperature and has the formul<\/span>a $$SOCl_2$$.\u00a0 It <span class=\"mt-color-000000\">reacts with carboxylic acids to produce an <\/span>acyl<span class=\"mt-color-000000\"> chloride, giving off\u00a0<\/span>sulfur<span class=\"mt-color-000000\"> dioxide and hydrogen chloride gases.\u00a0<\/span><span class=\"mt-color-000000\">For example:<\/span><\/p>\n<p style=\"text-align: center\">\\[ CH_3COOH\u00a0+ SOCl_2\u00a0\\rightarrow\u00a0CH_3COCl +SO_2 + \u00a0HCl\\]<\/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\/30160533\/OrganicCore_AcidHalides59.png\" alt=\"\" width=\"417px\" height=\"58px\" \/><\/p>\n<p><span class=\"mt-color-000000\">The separation is simplified to an extent because the by-products are both gases. Fractional distillation is still required to separate the <\/span>acyl<span class=\"mt-color-000000\"> chloride from any excess acid or <\/span>thionyl chloride<span class=\"mt-color-000000\">.<\/span><\/p>\n<\/div>\n<div id=\"section_4\" class=\"mt-section\">\n<h3 class=\"editable\"><span class=\"mt-color-000000\">Contributors<\/span><\/h3>\n<p>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>)<\/p>\n<h3>Video<\/h3>\n<p><iframe loading=\"lazy\" id=\"oembed-1\" title=\"Amides, anhydrides, esters, and acyl chlorides | Organic chemistry | Khan Academy\" width=\"500\" height=\"281\" src=\"https:\/\/www.youtube.com\/embed\/SRPQ62dR6b4?feature=oembed&#38;rel=0\" frameborder=\"0\" allowfullscreen=\"allowfullscreen\"><\/iframe><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"alignnone size-thumbnail wp-image-3020\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/08175258\/frame-44-150x150.png\" alt=\"\" width=\"150\" height=\"150\" \/><\/p>\n<section class=\"mt-content-container\">\n<div class=\"mt-section\">\n<header>\n<h2 id=\"title\">Hydrolysis of Amides<\/h2>\n<\/header>\n<section class=\"mt-content-container\">Generally, amides can be hydrolyzed in either acidic or basic solution. The mechanisms are much like those of ester hydrolysis (<a title=\"18.7: Reactions at the Carbonyl Carbon of Acid Derivatives\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Book%3A_Basic_Principles_of_Organic_Chemistry_(Roberts_and_Caserio)\/18%3A_Carboxylic_Acids_and_Their_Derivatives\/18.07%3A_Reactions_at_the_Carbonyl_Carbon_of_Acid_Derivatives#18-7A_Displacement_Reactions\" rel=\"internal\">Section 18-7A<\/a>), but the reactions are very much slower, a property of great biological importance (which we will discuss later):<img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30160902\/Roberts_and_Caserio_Screenshot_24-4-1.png\" alt=\"\" width=\"349px\" height=\"79px\" \/>Amide hydrolysis can be an important route to amines. Hydrolysis under acidic conditions requires strong acids such as sulfuric or hydrochloric, and temperatures of about $$100^\\text{o}$$ for several hours. The mechanism involves protonation of the amide on oxygen followed by attack of water on the carbonyl carbon. The tetrahedral intermediate formed dissociates ultimately to the carboxylic acid and the ammonium salt:<img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30160905\/Roberts_and_Caserio_Screenshot_24-4-2.png\" alt=\"\" width=\"408px\" height=\"200px\" \/>A brief summary of important amide reactions follows:<img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3773\/2018\/11\/30160913\/Roberts_and_Caserio_Screenshot_24-4-6.png\" alt=\"\" width=\"517px\" height=\"198px\" \/><\/p>\n<div id=\"section_1\" class=\"mt-section\">\n<h3 class=\"editable\">Contributors<\/h3>\n<ul>\n<li><span class=\"person_name\">John D. Robert <\/span>and <span class=\"person_name\">Marjorie C.<\/span> <span class=\"person_name\">Caserio <\/span>(1977) <em>Basic Principles of Organic Chemistry, second edition.<\/em> W. A. Benjamin, Inc. , Menlo Park, CA. ISBN 0-8053-8329-8. This content is copyrighted under the following conditions, &#8220;You are granted permission for individual, educational, research and non-commercial reproduction, distribution, display and performance of this work in any format.&#8221;<\/li>\n<\/ul>\n<\/div>\n<\/section>\n<\/div>\n<\/section>\n<\/div>\n<\/section>\n<\/div>\n<\/section>\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-2131\">\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>24.3: Synthesis of Amides. <strong>Authored by<\/strong>: John D. Robert and Marjorie C. Caserio . <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Book%3A_Basic_Principles_of_Organic_Chemistry_(Roberts_and_Caserio)\/24%3A_Organonitrogen_Compounds_II%3A_Amides%2C_Nitriles%2C_and_Nitro_Compounds\/24.3%3A_Synthesis_of_Amides\">https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Book%3A_Basic_Principles_of_Organic_Chemistry_(Roberts_and_Caserio)\/24%3A_Organonitrogen_Compounds_II%3A_Amides%2C_Nitriles%2C_and_Nitro_Compounds\/24.3%3A_Synthesis_of_Amides<\/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>15.7: Preparation of Esters. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Introductory_Chemistry\/Book%3A_The_Basics_of_GOB_Chemistry_(Ball_et_al.)\/15%3A_Organic_Acids_and_Bases_and_Some_of_Their_Derivatives\/15.07_Preparation_of_Esters\">https:\/\/chem.libretexts.org\/Textbook_Maps\/Introductory_Chemistry\/Book%3A_The_Basics_of_GOB_Chemistry_(Ball_et_al.)\/15%3A_Organic_Acids_and_Bases_and_Some_of_Their_Derivatives\/15.07_Preparation_of_Esters<\/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>Preparation of Acyl Chlorides. <strong>Authored by<\/strong>: Jim Clark. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Acid_Halides\/Synthesis_of_Acid_Halides\/Preparation_of_Acyl_Chlorides\">https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Supplemental_Modules_(Organic_Chemistry)\/Acid_Halides\/Synthesis_of_Acid_Halides\/Preparation_of_Acyl_Chlorides<\/a>. <strong>Project<\/strong>: Chemistry LibreText. <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>: Tim 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)\/12%3A_Acyl_substitution_reactions\/12.4%3A_Esters\">https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\/12%3A_Acyl_substitution_reactions\/12.4%3A_Esters<\/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>24.4: Hydrolysis of Amides. <strong>Authored by<\/strong>: John D. Robert and Marjorie C. Caserio. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Book%3A_Basic_Principles_of_Organic_Chemistry_(Roberts_and_Caserio)\/24%3A_Organonitrogen_Compounds_II%3A_Amides%2C_Nitriles%2C_and_Nitro_Compounds\/24.4%3A_Hydrolysis_of_Amides\">https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry\/Book%3A_Basic_Principles_of_Organic_Chemistry_(Roberts_and_Caserio)\/24%3A_Organonitrogen_Compounds_II%3A_Amides%2C_Nitriles%2C_and_Nitro_Compounds\/24.4%3A_Hydrolysis_of_Amides<\/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><\/ul><\/div>\n\t\t\t\t\t\t <\/div>\n\t\t\t\t\t <\/div>\n\t\t\t <\/section>","protected":false},"author":53384,"menu_order":3,"template":"","meta":{"_candela_citation":"[{\"type\":\"cc\",\"description\":\"24.3: Synthesis of Amides\",\"author\":\"John D. 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