{"id":1753,"date":"2025-09-12T21:47:43","date_gmt":"2025-09-12T21:47:43","guid":{"rendered":"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/outline_3\/"},"modified":"2025-09-12T21:52:03","modified_gmt":"2025-09-12T21:52:03","slug":"outline_3","status":"publish","type":"page","link":"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/chem263\/outlines\/outline_3\/","title":{"rendered":"Lecture Outline 3"},"content":{"rendered":"<h1 align=\"left\">Chem 263 &#8211; Lecture Outline &amp; Assignment #3<\/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_3_and_Assign3Oct2016.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 11 \u2013 Alcohols and Ethers &#8211; nomenclature and properties, prep &amp; reactions<\/li>\n<li>Chapter 12 \u2013 Alcohols from Carbonyl Compounds <\/li>\n<li>Chapter 16 \u2013 Aldehydes and Ketones &#8211; Carbonyl Reactions<\/li>\n<li>Chapter 18\u2013 Aldehydes and Ketones \u2013 Reactions at alpha-Carbon, Aldol<\/li>\n<li>Chapter 22 \u2013 Carbohydrates \u2013 read for overview structure and properties<\/li>\n<\/ul>\n<p align=\"right\"><a href=\"#Top\"><img loading=\"lazy\" decoding=\"async\" src=\"..\/..\/images\/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 11:<br \/>\n  <\/strong>11.2; 11.3; 11.5 to 11.7; 11.11 to 11.13; 11.15 to 11.17; 11.20; 11.23;11.25; 11.26; 11.28; 11.32<\/p>\n<p><strong>Chapter 12:<br \/>\n  <\/strong>12.1; 12.3 to 12.8; 12.10; 12.11<\/p>\n<p><strong>Chapter 16:<br \/>\n  <\/strong>16.1; 16.4; 16.7; 16.9 to 16.11; 16.17; 16.19; 16.28<\/p>\n<p><strong>Chapter 18:<br \/>\n  <\/strong>18.1; 18.2; 18.6a; 18.16; 18.19<\/p>\n<p><strong>Chapter 22:<br \/>\n  <\/strong>22.1; 22.2; 22.3; 22.5; 22.20; 22.28<\/p>\n<\/blockquote>\n<p align=\"right\"><a href=\"#Top\"><img loading=\"lazy\" decoding=\"async\" src=\"..\/..\/images\/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<p><a name=\"Outline\" id=\"Outline\" \/><\/p>\n<h2><strong>Lecture Outline 3: <\/strong><strong>Review of Stereochemistry, Alcohols and Ethers; <\/strong><strong>Aldehydes &amp; Ketones &#8211; Properties of the Carbonyl Group<\/strong><\/h2>\n<ol>\n<li><strong> Structure, Nomenclature and Physical Properties of Alcohols and Ethers\n<p>  <\/strong><\/p>\n<ol type=\"A\">\n<li>Aliphatic Alcohols\n<\/li>\n<li>Aromatic Alcohols (Phenols)\n<\/li>\n<li>Ethers\n<\/li>\n<li>Alcohols and Phenols &#8211; general properties\n<ol>\n<li>MP, BP, solubility, density &#8211; hydrogen bonding<\/li>\n<li>Acidity of Aliphatic Alcohols (ROH)\n<\/li>\n<\/ol>\n<\/li>\n<li>Acidity of Phenols (ArOH) &#8211; resonance\n<\/li>\n<li>Physical Properties of Ethers\n<p>\n        <\/li>\n<\/ol>\n<\/li>\n<li><strong>Review of Stereochemistry &#8211; &#8220;Fixed three dimensional arrangements&#8221;<\/strong>\n<ol type=\"A\">\n<li>The Concept of Chirality\n<ol>\n<li>Identification of chiral objects and molecules &#8211; definitions<\/li>\n<li>Types of stereoisomers &#8211; enantiomers and diastereomers<\/li>\n<li>Racemic mixtures &#8211; 50-50 mixtures of enantiomers\n<\/li>\n<\/ol>\n<\/li>\n<li>The R and S\u00a0 Nomenclature System\n<ol>\n<li>Rules for assignment of R and S configurations\n<\/li>\n<\/ol>\n<\/li>\n<li>Molecules with more than one chiral center\n<ol>\n<li>Enantiomers and Diastereomers<\/li>\n<li>Meso compounds &#8211; chiral centers with plane of symmetry within molecule<\/li>\n<li>Recognition of chiral centers in complex molecules\n<\/li>\n<\/ol>\n<\/li>\n<\/ol>\n<\/li>\n<li><strong>Structure, Nomenclature, Properties of Aldehydes and Ketones<\/strong>\n<ol type=\"A\">\n<li>Nature of the Carbonyl Group &#8211; Physical Properties\n<ol>\n<li>Polarity and Reactivity<\/li>\n<li>Hybridization and shape (sp<sup>2<\/sup>, planar)<\/li>\n<li>Physical Properties &#8211; BP, MP, solubility, smell\n<\/li>\n<\/ol>\n<\/li>\n<li>Nomenclature of Aldehydes &#8211; RCHO\n<ol>\n<li>IUPAC &#8211; alkane name, replace &#8220;e&#8221; with &#8220;al&#8221;\n<\/li>\n<\/ol>\n<\/li>\n<li>Nomenclature of Ketones &#8211; RCOR\n<ol>\n<li>IUPAC &#8211; alkane name &#8211; replace &#8220;e&#8221; with &#8220;one&#8221;\n<p>\n            <\/li>\n<\/ol>\n<\/li>\n<\/ol>\n<\/li>\n<li><strong>Preparation of Aldehydes and Ketones\n<p>    <\/strong><\/p>\n<ol type=\"A\">\n<li>Aldehydes\n<ol>\n<li>Oxidation of Primary Alcohol: RCH<sub>2<\/sub>OH\u00a0 -&gt; RCHO<\/li>\n<li>Reduction of Acyl Halides: RCOX\u00a0 -&gt; RCHO\n<\/li>\n<\/ol>\n<\/li>\n<li>Ketones\n<ol>\n<li>Friedel-Crafts Acylations<\/li>\n<li>Oxidation of 2\u00b0 Alcohols: R<sub>2<\/sub>CHOH to\u00a0 R<sub>2<\/sub>CO<\/li>\n<li>With Organometals: RMgX, R<sub>2<\/sub>Cd, R<sub>2<\/sub>CuLi\n<p>\n            <\/li>\n<\/ol>\n<\/li>\n<\/ol>\n<\/li>\n<li><strong>Reactions of Aldehydes and Ketones<\/strong>\n<ol type=\"A\">\n<li>Nucleophilic Additions at the Carbonyl Carbon Atom\n<ol>\n<li>General considerations &#8211; strong vs. weak nucleophiles<\/li>\n<li>Cyanohydrin formation<\/li>\n<li>Grignard reagent addition<\/li>\n<li>Reduction (hydride addition)<\/li>\n<li>Hemiacetal and Acetal formation\n<\/li>\n<\/ol>\n<\/li>\n<li>Nucleophilic Addition &#8211; Elimination at the Carbonyl Carbon\n<ol>\n<li>Wittig Reaction<\/li>\n<li>Addition of Derivatives of Ammonia: formation of oximes, hydrazones, imines<\/li>\n<li>Cannizzaro Reaction of Aldehydes with no alpha hydrogen\n<\/li>\n<\/ol>\n<\/li>\n<li>Reactions at the alpha-carbon\n<ol>\n<li>Enolate formations &#8211; Keto &#8211; enol tautomerism<\/li>\n<li>Halogenation and Haloform Reaction<\/li>\n<li>Alkylation<\/li>\n<li>Aldol Addition\n<\/li>\n<\/ol>\n<\/li>\n<li>Reactions of alpha,beta-unsaturated aldehydes and ketones\n<ol>\n<li>Conjugate Addition vs Simple Addition\n<p>\n          <\/li>\n<\/ol>\n<\/li>\n<\/ol>\n<\/li>\n<li><strong>Carbohydrates<\/strong>\n<ol type=\"A\">\n<li>Monosaccharides\n<ol>\n<li>Classification &#8211; aldose, ketose, triose, tetrose, etc.<\/li>\n<li>Stereoisomerism<\/li>\n<li>Anomers and Ring Formation (Hemiacetals, Acetals)<\/li>\n<li>Properties and Sweet Taste\n<\/li>\n<\/ol>\n<\/li>\n<li>Disaccharides and Polysaccharides\n<ol>\n<li>Sucrose<\/li>\n<li>Cellulose, Starch, Glycogen<\/li>\n<\/ol>\n<\/li>\n<\/ol>\n<\/li>\n<\/ol>\n<p align=\"right\"><a href=\"#Top\"><img loading=\"lazy\" decoding=\"async\" src=\"..\/..\/images\/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","protected":false},"excerpt":{"rendered":"<p>Chem 263 &#8211; Lecture Outline &amp; Assignment #3 \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_3\/\" class=\"more-link\">&#8230;<span class=\"screen-reader-text\">  Lecture Outline 3<\/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-1753","page","type-page","status-publish","hentry"],"_links":{"self":[{"href":"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/wp-json\/wp\/v2\/pages\/1753","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=1753"}],"version-history":[{"count":2,"href":"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/wp-json\/wp\/v2\/pages\/1753\/revisions"}],"predecessor-version":[{"id":1759,"href":"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/wp-json\/wp\/v2\/pages\/1753\/revisions\/1759"}],"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=1753"}],"wp:term":[{"taxonomy":"wf_page_folders","embeddable":true,"href":"https:\/\/spaces.facsci.ualberta.ca\/vederaslab\/wp-json\/wp\/v2\/wf_page_folders?post=1753"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}