2009 2 Introduction to Carbonyls - Introduction to Carbonyl...

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Introduction to Carbonyl Chemistry 1. Definition of Aldehydes and Ketones ome common carbonyl ontaining compounds 1 2 . Some common carbonyl-containing compounds 3 . Oxidation state 4. Physical properties 5 . Overview of Chemical Reactivity ABENOR 6 . Top 12 reactions! Lecture 2 2009
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Assignment 1 (McMurry 6e) Topic Chapter Section Problems Preview p.672 - 681 II, III p. 674-676 Nomenclature 19.1 19.1, 19.2 Nucleophilic addition 19.4, 19.5 19.6 Hydration 19.6 19.7, 19.8 Acetal Formation 19.11 19.14,19.15,19.38 2 Imine/Enamine 19.9 19.10, 19.11 Cyanohydrins 19.7 19.9 Grignard Addition 19.8 17.10 Wittig 19.12 19.16, 19.49 Hydride Reduction 19.8 19.71 Oxidation 17.8,19.3
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Assignment 1 (McMurry 7e) Topic Chapter Section Problems Preview p.688 - 694 II, III p. 688-690 Nomenclature 19.1 19.1, 19.2 Nucleophilic addition 19.4, 19.5 19.6 Hydration 19.5 19.7, 19.8 Acetal Formation 19.10 19.14,19.15,19.39 3 Imine/Enamine 19.8 19.10, 19.11 Cyanohydrins 19.6 19.9 Grignard Addition 19.7 17.10 Wittig 19.11,19.12 19.16, 19.17, 19.51 Hydride Reduction 19.8,19.12 19.73 Oxidation 17.7,19.3
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Simple Carbonyl-Containing Compounds O O 4 R R R H Ketones Aldehydes All aldehydes have (at least) one hydrogen attached to the Carbonyl carbon. All ketones have 2 carbons attached to the C=O group
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Origin of Names • Aldehydes - dehydro genated al cohol CH 3 CH 2 OH CH 3 C(H)=O 5 • Ketones - a cetone
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Some common carbonyl- containing compounds 6 acetone formaldehyde
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Yumm! 7 vanillin cinnamaldehyde Raspberry ketone
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Mmmm… Marine Green floral fruity 8 Odorants woody Musk amber L. A. Saudan, Firmenich SA, Geneva Acc. Chem. Res., 40 (12), 1309– 1319
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Oxidation state of Aldehydes and Ketones Eg. For C1 compounds: 9 Adding O, removing H = oxidation
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Oxidation States of C-2 compounds C H 3 CH 3 -2H [O] Alcohols & Alkene at the same [O] level H H H H hydration 10 at the same [O] level H H -2H [O] hydration H O O H O H OH [O] + [O] 2
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Degree of Unsaturation • 1 degree of unsaturation per carbonyl Degree of unsaturation = Max # hydrogens – Observed # hydrogens 2 11 Example: C O C H 3 C H 3 C 3 H 6 O Degree of unsaturation =
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2009 2 Introduction to Carbonyls - Introduction to Carbonyl...

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