{"id":1744,"date":"2025-09-12T21:39:13","date_gmt":"2025-09-12T21:39:13","guid":{"rendered":"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/outline_4\/"},"modified":"2025-09-12T21:57:24","modified_gmt":"2025-09-12T21:57:24","slug":"outline_4","status":"publish","type":"page","link":"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/chem263\/outlines\/outline_4\/","title":{"rendered":"Lecture Outline 4"},"content":{"rendered":"<h1 align=\"left\">Chem 263 &#8211; Lecture Outline &amp; Assignment #4<\/h1>\n<p align=\"left\">\u00a0<\/p>\n<blockquote>\n<p><a href=\"#Readings\">Readings<\/a><br \/>\n  <a href=\"#Problems\">Problems<\/a><br \/>\n  <a href=\"#Outline\">Outline<\/a><br \/>\n  <a href=\"pdf\/C263_Out_4_and_Assign4Nov16.pdf\" target=\"_blank\">Download pdf<\/a><\/p>\n<\/blockquote>\n<p align=\"left\">\u00a0<\/p>\n<h2><b><a name=\"Readings\" \/>Readings:<\/b><\/h2>\n<p \/>\n<p>TWG Solomons and CB Fryhle &#8220;Organic Chemistry&#8221; 11th Edition (2014):<\/p>\n<ul>\n<li>Functional Group List on p 76  and<\/li>\n<li>Relative Strength of Acids and Bases on Inside Front Cover &#8211; same table page 111 (page 101 9th Edition &amp; page 105 &#8211; 8th Edition<\/li>\n<li>Chapter 17\u2013 Carboxylic Acids and their Derivatives<\/li>\n<li>Chapter 18\u2013 Reactions at alpha-carbon of carbonyl<\/li>\n<li>Chapter 23 \u2013 Lipids<\/li>\n<\/ul>\n<p align=\"right\"><a href=\"#Top\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/wp-content\/uploads\/sites\/123\/2025\/08\/top_down.jpg\" alt=\"Top\" width=\"27\" height=\"16\" hspace=\"20\" border=\"0\" id=\"Top1\" \/><\/a>\n<\/p>\n<hr align=\"left\" width=\"100%\" \/>\n<p>\u00a0<\/p>\n<h2><b><a name=\"Problems\" id=\"Problems\" \/>Problems:<\/b><\/h2>\n<p>Do Not turn in, answers available in &#8220;Study Guide and Solutions Manual for Organic Chemistry&#8221; by Solomons and Fryhle.<\/p>\n<blockquote>\n<p><strong>Chapter 17:<br \/>\n  <\/strong> 17.1; 17.3 to 17.6; 17.8; 17.10; 17.18; 17.19; 17.22; 17.23; 17.25;17.26; 17.28; 17.33<\/p>\n<p><strong>Chapter 18:<br \/>\n  <\/strong> 18.2; 18.3; 18.15; 18.18<\/p>\n<p><strong>Chapter 23:<br \/>\n  <\/strong> 23.1; 23.2; 23.3; 23.6; 23.7; 23.8; 23.9<\/p>\n<\/blockquote>\n<p align=\"right\"><a href=\"#Top\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/wp-content\/uploads\/sites\/123\/2025\/08\/top_down.jpg\" alt=\"Top\" width=\"27\" height=\"16\" hspace=\"20\" border=\"0\" id=\"Top2\" \/><\/a>\n<\/p>\n<hr align=\"left\" width=\"100%\" \/>\n<p>\u00a0<\/p>\n<h2><b><a name=\"Outline\" id=\"Outline\" \/><\/b><strong>Lecture Outline 4: <\/strong> <strong>Carboxylic Acids and Their Derivatives<\/strong><\/h2>\n<ol>\n<li><strong> Structure and Nomenclature &#8211; The Acyl Group\n<p>  <\/strong><\/p>\n<ol type=\"A\">\n<li> Acids &#8211; RCOOH\n<\/li>\n<li> Acid Halides &#8211; RCOX\n<\/li>\n<li> Anhydrides &#8211; (RCO)<sub>2<\/sub>O\n<\/li>\n<li> Esters &#8211; RCOOR&#8217;\n<\/li>\n<li>Amides &#8211; RCONH<sub>2<\/sub>, RCONHR, RCONR<sub>2<\/sub>\n<p>\n        <\/li>\n<\/ol>\n<\/li>\n<li> <strong>Carboxylic Acids <\/strong>\n<ol type=\"A\">\n<li> Acidity and Physical Properties\n<\/li>\n<li> Preparation \n<ol>\n<li>Oxidation of Alkenes<\/li>\n<li> Oxidation of Alcohols and Aldehydes <\/li>\n<li> Oxidation of Alkylbenzenes <\/li>\n<li> Oxidation of Methyl Ketones (Haloform reaction) <\/li>\n<li> Hydrolysis of Nitriles <\/li>\n<li> Carbonation of Grignard Reagents (RMgX + CO<sub>2<\/sub>)\n<\/li>\n<\/ol>\n<\/li>\n<li> Reactions\n<ol>\n<li> Salt formation <\/li>\n<li> Ester formation <\/li>\n<li> Reduction\n<p>\n      <\/li>\n<\/ol>\n<\/li>\n<\/ol>\n<\/li>\n<li> <strong>Acid Halides<\/strong>\n<ol type=\"A\">\n<li> Physical Properties and Reactivity\n<\/li>\n<li> Preparation from Carboxylic Acids\n<\/li>\n<li>Reactions on Carbonyl Carbon &#8211; (Nucleophilic Substitution)\n<ol>\n<li> Hydrolysis to Carboxylic Acids <\/li>\n<li> Anhydride Formation with Carboxylates <\/li>\n<li> Alcoholysis to Esters <\/li>\n<li> Ammonolysis to Amides <\/li>\n<li> Reduction to Alcohols or Aldehydes <\/li>\n<li> Friedel Crafts Acylations\n<\/li>\n<\/ol>\n<\/li>\n<li>Reaction on alpha-carbon &#8211; Perkin Reaction\n<p><\/p>\n<\/li>\n<\/ol>\n<\/li>\n<li><strong> Anhydrides\n<p>    <\/strong><\/p>\n<ol type=\"A\">\n<li> Physical Properties\n<\/li>\n<li> Preparation\n<ol>\n<li>From Acid Halides and Carboxylates<\/li>\n<li>Cyclic Dehydration of Diacids\n<\/li>\n<\/ol>\n<\/li>\n<li> Reactions on Carbonyl Carbon \n<ol>\n<li> Hydrolysis to Carboxylic Acids<\/li>\n<li> Alcoholysis to Ester and Acid <\/li>\n<li> Ammonolysis to Amide and Salt of Acid <\/li>\n<li> Reduction to Alcohols <\/li>\n<li> Friedel Crafts Acylations\n<\/li>\n<\/ol>\n<\/li>\n<li> Reaction on alpha-carbon &#8211; Perkin Reaction\n<p>\n      <\/li>\n<\/ol>\n<\/li>\n<li> <strong>Esters<\/strong>\n<ol type=\"A\">\n<li> Physical Properties\n<\/li>\n<li> Preparation\n<ol>\n<li> Alcoholysis of Acid Halides <\/li>\n<li> Alcoholysis of Anhydrides <\/li>\n<li> Esterification of Carboxylic Acids\n<ol type=\"a\">\n<li> Primary and Secondary ROH<\/li>\n<li> Tertiary ROH <\/li>\n<li> Lactone formation\n<\/li>\n<\/ol>\n<\/li>\n<\/ol>\n<\/li>\n<li> Reactions at Carbonyl Carbon\n<ol>\n<li> Acidic Hydrolysis &#8211; Acyl &#8211; Oxygen and Alkyl &#8211; Oxygen Cleavage <\/li>\n<li> Alkaline Hydrolysis &#8211; Acyl &#8211; Oxygen Cleavage <\/li>\n<li> Transesterification with Alcohols <\/li>\n<li> Ammonolysis to Amide and Alcohol<\/li>\n<li> Reduction to Alcohols <\/li>\n<li> Grignard Reaction\n<\/li>\n<\/ol>\n<\/li>\n<li> Reactions at alpha-carbon\n<ol>\n<li> Ester-Ester Condensation &#8211; Claisen and Dieckmann <\/li>\n<li> Ester-Ketone and Ester-Aldehyde Condensation\n<\/li>\n<\/ol>\n<\/li>\n<li> Fats, Waxes, and Soaps\n<p>\n      <\/li>\n<\/ol>\n<\/li>\n<li> <strong>Amides<\/strong>\n<ol type=\"A\">\n<li>Physical Properties\n<\/li>\n<li> Preparation\n<ol>\n<li> Ammonolysis of Acid Halides, Anhydrides, Esters <\/li>\n<li> Partial Hydrolysis of Nitriles\n<\/li>\n<\/ol>\n<\/li>\n<li> Reactions at Carbonyl Carbon\n<ol>\n<li> Hydrolysis                    <\/li>\n<li> Reduction to Amines <\/li>\n<\/ol>\n<\/li>\n<\/ol>\n<\/li>\n<\/ol>\n<p align=\"right\"><a href=\"#Top\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/wp-content\/uploads\/sites\/123\/2025\/08\/top_down.jpg\" alt=\"Top\" width=\"27\" height=\"16\" hspace=\"20\" border=\"0\" \/><\/a>\n<\/p>\n<hr align=\"left\" width=\"100%\" \/>\n<p>\u00a0<\/p>\n<p>\u00a0<\/p>\n<p>\u00a0<\/p>\n<p>\u00a0<\/p>\n<p>\u00a0<\/p>\n<p>\u00a0<\/p>\n<p>\u00a0<\/p>\n<p>\u00a0<\/p>\n<p>\u00a0<\/p>\n<h2>\u00a0<\/h2>\n","protected":false},"excerpt":{"rendered":"<p>Chem 263 &#8211; Lecture Outline &amp; Assignment #4 \u00a0 Readings Problems Outline Download pdf \u00a0 Readings: TWG Solomons and CB Fryhle &#8220;Organic Chemistry&#8221; 11th Edition (2014): Functional Group List on p 76 and Relative Strength of Acids and Bases on Inside Front Cover &#8211; same table page 111 (page 101 9th Edition &amp; page 105 <a href=\"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/chem263\/outlines\/outline_4\/\" class=\"more-link\">&#8230;<span class=\"screen-reader-text\">  Lecture Outline 4<\/span><\/a><\/p>\n","protected":false},"author":117,"featured_media":0,"parent":1199,"menu_order":0,"comment_status":"closed","ping_status":"closed","template":"templates\/chem263.php","meta":{"footnotes":""},"wf_page_folders":[7],"class_list":["post-1744","page","type-page","status-publish","hentry"],"_links":{"self":[{"href":"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/wp-json\/wp\/v2\/pages\/1744","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/wp-json\/wp\/v2\/pages"}],"about":[{"href":"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/wp-json\/wp\/v2\/types\/page"}],"author":[{"embeddable":true,"href":"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/wp-json\/wp\/v2\/users\/117"}],"replies":[{"embeddable":true,"href":"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/wp-json\/wp\/v2\/comments?post=1744"}],"version-history":[{"count":4,"href":"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/wp-json\/wp\/v2\/pages\/1744\/revisions"}],"predecessor-version":[{"id":1762,"href":"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/wp-json\/wp\/v2\/pages\/1744\/revisions\/1762"}],"up":[{"embeddable":true,"href":"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/wp-json\/wp\/v2\/pages\/1199"}],"wp:attachment":[{"href":"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/wp-json\/wp\/v2\/media?parent=1744"}],"wp:term":[{"taxonomy":"wf_page_folders","embeddable":true,"href":"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/wp-json\/wp\/v2\/wf_page_folders?post=1744"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}