{"id":1602,"date":"2018-03-21T15:31:33","date_gmt":"2018-03-21T15:31:33","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-orgbiochemistry\/chapter\/preparation-of-esters\/"},"modified":"2018-05-09T16:54:06","modified_gmt":"2018-05-09T16:54:06","slug":"preparation-of-esters","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-orgbiochemistry\/chapter\/preparation-of-esters\/","title":{"raw":"15.8 Preparation of Esters","rendered":"15.8 Preparation of Esters"},"content":{"raw":"<div id=\"navbar-top\" class=\"navbar\"><\/div>\r\n<div id=\"book-content\">\r\n<div id=\"gob-ch15_s08\" class=\"section\" xml:lang=\"en\">\r\n<div class=\"textbox learning-objectives\">\r\n<h3>Learning Objectives<\/h3>\r\n<div id=\"gob-ch15_s08_n01\" class=\"learning_objectives editable block\">\r\n<ol id=\"gob-ch15_s08_l01\" class=\"orderedlist\">\r\n \t<li>Identify and describe the substances from which most esters are prepared.<\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n<p id=\"gob-ch15_s08_p01\" class=\"para editable block\">Some esters can be prepared by <span class=\"margin_term\"><span class=\"glossterm\">esterification<\/span><span class=\"glossdef\">The formation of an ester from a carboxylic acid and an alcohol.<\/span><\/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>\r\n\r\n<div id=\"fwk-gob-eq15_003\" class=\"informalfigure large block\"><img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21153121\/0349eb85db710b927a53b2862148f4d7.jpg\" alt=\"image\" \/><\/div>\r\n<p id=\"gob-ch15_s08_p02\" class=\"para editable block\">The reaction is reversible. As a specific example of an esterification reaction, butyl acetate can be made from acetic acid and 1-butanol.<\/p>\r\n\r\n<div id=\"fwk-gob-eq15_004\" class=\"informalfigure large block\"><img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21153123\/894ff755fad4801d9a41cea4578958d9.jpg\" alt=\"image\" \/><\/div>\r\n<div id=\"gob-ch15_s08_n02\" class=\"callout block\">\r\n<div class=\"textbox shaded\">\r\n<h3 class=\"title\">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=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21153126\/50055548001cd5ef95a7a9bbdfb0e274.jpg\" alt=\"image\" \/><\/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>\r\n<div id=\"gob-ch15_s08_qs01\" class=\"qandaset block\">\r\n<div class=\"textbox exercises\">\r\n<div id=\"gob-ch15_s08_qs01\" class=\"qandaset block\">\r\n<h3 class=\"title\">Concept Review Exercises<\/h3>\r\n<ol id=\"gob-ch15_s08_qs01_qd01\" class=\"qandadiv\">\r\n \t<li id=\"gob-ch15_s08_qs01_qd01_qa01\" class=\"qandaentry\">\r\n<div class=\"question\">\r\n<p id=\"gob-ch15_s08_qs01_p01\" class=\"para\">From what carboxylic acid and what alcohol can the ester isopropyl nonanoate be made?<\/p>\r\n\r\n<\/div><\/li>\r\n \t<li id=\"gob-ch15_s08_qs01_qd01_qa02\" class=\"qandaentry\">\r\n<div class=\"question\">\r\n<p id=\"gob-ch15_s08_qs01_p03\" class=\"para\">From what carboxylic acid and what alcohol can the ester cyclobutyl butyrate be made?<\/p>\r\n\r\n<\/div><\/li>\r\n<\/ol>\r\n<\/div>\r\n<div id=\"gob-ch15_s08_qs01_ans\" class=\"qandaset block\">\r\n<div class=\"answer\">\r\n<p id=\"gob-ch15_s08_qs01_p02_ans\" class=\"para\">[reveal-answer q=\"225673\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"225673\"]<\/p>\r\n\r\n<ol>\r\n \t<li class=\"para\">nonanoic acid and isopropyl alcohol<\/li>\r\n \t<li class=\"para\">butyric acid and cyclobutyl alcohol\u00a0[\/hidden-answer]<\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div class=\"textbox key-takeaways\">\r\n<div id=\"gob-ch15_s08_qs01\" class=\"qandaset block\">\r\n<h3 class=\"title\">Key Takeaway<\/h3>\r\n<\/div>\r\n<div id=\"gob-ch15_s08_n04\" class=\"key_takeaways editable block\">\r\n<ul id=\"gob-ch15_s08_l03\" class=\"itemizedlist\">\r\n \t<li>Esters are made by the reaction of a carboxylic acid with an alcohol, a process that is called esterification.<\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"gob-ch15_s08_qs02_ans\" class=\"qandaset block\">\r\n<div class=\"textbox exercises\">\r\n<div id=\"gob-ch15_s08_qs02\" class=\"qandaset block\">\r\n<h3 class=\"title\">Exercises<\/h3>\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\">\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\">\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>\r\n&nbsp;<\/li>\r\n<\/ol>\r\n[reveal-answer q=\"528893\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"528893\"]\r\n\r\n1. a.\u00a0<img class=\"aligncenter\" src=\"https:\/\/saylordotorg.github.io\/text_the-basics-of-general-organic-and-biological-chemistry\/section_18\/86e0be0809a99e5a69c163a26eb86bca.jpg\" \/>\r\n\r\nb.\u00a0<img class=\"aligncenter\" src=\"https:\/\/saylordotorg.github.io\/text_the-basics-of-general-organic-and-biological-chemistry\/section_18\/a6860c182a9c3f3509fc2de8e62f7e50.jpg\" \/>[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>","rendered":"<div id=\"navbar-top\" class=\"navbar\"><\/div>\n<div id=\"book-content\">\n<div id=\"gob-ch15_s08\" class=\"section\" xml:lang=\"en\">\n<div class=\"textbox learning-objectives\">\n<h3>Learning Objectives<\/h3>\n<div id=\"gob-ch15_s08_n01\" class=\"learning_objectives editable block\">\n<ol id=\"gob-ch15_s08_l01\" class=\"orderedlist\">\n<li>Identify and describe the substances from which most esters are prepared.<\/li>\n<\/ol>\n<\/div>\n<\/div>\n<p id=\"gob-ch15_s08_p01\" class=\"para editable block\">Some esters can be prepared by <span class=\"margin_term\"><span class=\"glossterm\">esterification<\/span><span class=\"glossdef\">The formation of an ester from a carboxylic acid and an alcohol.<\/span><\/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 id=\"fwk-gob-eq15_003\" class=\"informalfigure large block\"><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21153121\/0349eb85db710b927a53b2862148f4d7.jpg\" alt=\"image\" \/><\/div>\n<p id=\"gob-ch15_s08_p02\" class=\"para editable block\">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\" class=\"informalfigure large block\"><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21153123\/894ff755fad4801d9a41cea4578958d9.jpg\" alt=\"image\" \/><\/div>\n<div id=\"gob-ch15_s08_n02\" class=\"callout block\">\n<div class=\"textbox shaded\">\n<h3 class=\"title\">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 decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/3101\/2018\/03\/21153126\/50055548001cd5ef95a7a9bbdfb0e274.jpg\" alt=\"image\" \/><\/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>\n<div id=\"gob-ch15_s08_qs01\" class=\"qandaset block\">\n<div class=\"textbox exercises\">\n<div id=\"gob-ch15_s08_qs01\" class=\"qandaset block\">\n<h3 class=\"title\">Concept Review Exercises<\/h3>\n<ol id=\"gob-ch15_s08_qs01_qd01\" class=\"qandadiv\">\n<li id=\"gob-ch15_s08_qs01_qd01_qa01\" class=\"qandaentry\">\n<div class=\"question\">\n<p id=\"gob-ch15_s08_qs01_p01\" class=\"para\">From what carboxylic acid and what alcohol can the ester isopropyl nonanoate be made?<\/p>\n<\/div>\n<\/li>\n<li id=\"gob-ch15_s08_qs01_qd01_qa02\" class=\"qandaentry\">\n<div class=\"question\">\n<p id=\"gob-ch15_s08_qs01_p03\" class=\"para\">From what carboxylic acid and what alcohol can the ester cyclobutyl butyrate be made?<\/p>\n<\/div>\n<\/li>\n<\/ol>\n<\/div>\n<div id=\"gob-ch15_s08_qs01_ans\" class=\"qandaset block\">\n<div class=\"answer\">\n<p id=\"gob-ch15_s08_qs01_p02_ans\" class=\"para\">\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q225673\">Show Answer<\/span><\/p>\n<div id=\"q225673\" class=\"hidden-answer\" style=\"display: none\">\n<ol>\n<li class=\"para\">nonanoic acid and isopropyl alcohol<\/li>\n<li class=\"para\">butyric acid and cyclobutyl alcohol\u00a0<\/div>\n<\/div>\n<\/li>\n<\/ol>\n<\/div>\n<\/div>\n<\/div>\n<div class=\"textbox key-takeaways\">\n<div id=\"gob-ch15_s08_qs01\" class=\"qandaset block\">\n<h3 class=\"title\">Key Takeaway<\/h3>\n<\/div>\n<div id=\"gob-ch15_s08_n04\" class=\"key_takeaways editable block\">\n<ul id=\"gob-ch15_s08_l03\" class=\"itemizedlist\">\n<li>Esters are made by the reaction of a carboxylic acid with an alcohol, a process that is called esterification.<\/li>\n<\/ul>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"gob-ch15_s08_qs02_ans\" class=\"qandaset block\">\n<div class=\"textbox exercises\">\n<div id=\"gob-ch15_s08_qs02\" class=\"qandaset block\">\n<h3 class=\"title\">Exercises<\/h3>\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\">\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\">\n<li>methanol<\/li>\n<li>1-propanol in the presence of a mineral acid catalyst<\/li>\n<\/ol>\n<\/div>\n<p>&nbsp;<\/li>\n<\/ol>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q528893\">Show Answer<\/span><\/p>\n<div id=\"q528893\" class=\"hidden-answer\" style=\"display: none\">\n<p>1. a.\u00a0<img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/saylordotorg.github.io\/text_the-basics-of-general-organic-and-biological-chemistry\/section_18\/86e0be0809a99e5a69c163a26eb86bca.jpg\" alt=\"image\" \/><\/p>\n<p>b.\u00a0<img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/saylordotorg.github.io\/text_the-basics-of-general-organic-and-biological-chemistry\/section_18\/a6860c182a9c3f3509fc2de8e62f7e50.jpg\" alt=\"image\" \/><\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\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-1602\">\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>The Basics of General, Organic, and Biological Chemistry v. 1.0. <strong>Provided by<\/strong>: Saylor Academy. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"https:\/\/saylordotorg.github.io\/text_the-basics-of-general-organic-and-biological-chemistry\/\">https:\/\/saylordotorg.github.io\/text_the-basics-of-general-organic-and-biological-chemistry\/<\/a>. <strong>License<\/strong>: <em><a target=\"_blank\" rel=\"license\" href=\"https:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/\">CC BY-NC: Attribution-NonCommercial<\/a><\/em>. <strong>License Terms<\/strong>: This text was adapted by Saylor Academy under a Creative Commons Attribution-NonCommercial-ShareAlike 3.0 License without attribution as requested by the work&#039;s original creator or licensor.<\/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":9,"template":"","meta":{"_candela_citation":"[{\"type\":\"cc\",\"description\":\"The Basics of 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licensor.\"}]","CANDELA_OUTCOMES_GUID":"","pb_show_title":"on","pb_short_title":"","pb_subtitle":"","pb_authors":[],"pb_section_license":""},"chapter-type":[],"contributor":[],"license":[],"class_list":["post-1602","chapter","type-chapter","status-publish","hentry"],"part":1500,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-orgbiochemistry\/wp-json\/pressbooks\/v2\/chapters\/1602","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/courses.lumenlearning.com\/suny-orgbiochemistry\/wp-json\/pressbooks\/v2\/chapters"}],"about":[{"href":"https:\/\/courses.lumenlearning.com\/suny-orgbiochemistry\/wp-json\/wp\/v2\/types\/chapter"}],"author":[{"embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-orgbiochemistry\/wp-json\/wp\/v2\/users\/53384"}],"version-history":[{"count":6,"href":"https:\/\/courses.lumenlearning.com\/suny-orgbiochemistry\/wp-json\/pressbooks\/v2\/chapters\/1602\/revisions"}],"predecessor-version":[{"id":2955,"href":"https:\/\/courses.lumenlearning.com\/suny-orgbiochemistry\/wp-json\/pressbooks\/v2\/chapters\/1602\/revisions\/2955"}],"part":[{"href":"https:\/\/courses.lumenlearning.com\/suny-orgbiochemistry\/wp-json\/pressbooks\/v2\/parts\/1500"}],"metadata":[{"href":"https:\/\/courses.lumenlearning.com\/suny-orgbiochemistry\/wp-json\/pressbooks\/v2\/chapters\/1602\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-orgbiochemistry\/wp-json\/wp\/v2\/media?parent=1602"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-orgbiochemistry\/wp-json\/pressbooks\/v2\/chapter-type?post=1602"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-orgbiochemistry\/wp-json\/wp\/v2\/contributor?post=1602"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-orgbiochemistry\/wp-json\/wp\/v2\/license?post=1602"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}