Chapter27 - Chapter 27. Biomolecules: Lipids Based on...

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Chapter 27. Biomolecules: Lipids Based on McMurry’s Organic Chemistry, 6th edition ©2003 Ronald Kluger Department of Chemistry University of Toronto
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Based on McMurry, Organic Chemistry, Chapter 27, 6th 2 About Lipids Naturally materials that preferentially extract into nonpolar organic solvents Includes fats, oils, waxes, some vitamins and hormones, some components of membrane General types: esters (“saponifiable”) and those that can’t be hydrolyzed
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Based on McMurry, Organic Chemistry, Chapter 27, 6th 3 27.1 Waxes, Fats, and Oils Waxes - contain esters formed from long-chain (C16- C36) carboxylic acids and long-chain alcohols (C24- C36) Triacontyl hexadecanoate is in beeswax
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Based on McMurry, Organic Chemistry, Chapter 27, 6th 4 Fats and Oils Animal fats and vegetable are triacylglycerols oil Triesters of glycerol with three long-chain carboxylic acids Saponification of a fat or oil with (reaction with aqueous NaOH) yields glycerol and three fatty acids
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Based on McMurry, Organic Chemistry, Chapter 27, 6th 5 Fatty Acids (from Fats and Oils) Straight-chain (C 12 - C 20 ) carboxylic acids Double bonds are cis-substituted but trans-fatty acid also occur A fat or oil in nature occurs as a mixture of many different triacylglycerols The most abundant saturated fatty acids are palmitic (C 16 ) and stearic (C 18 )
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Based on McMurry, Organic Chemistry, Chapter 27, 6th 6 Unsaturated and Polyunsaturated Fatty Acids Oleic (C 18 with one C=C) and linolenic (C 18 with 3 C=C) are the most abundant unsaturated
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Based on McMurry, Organic Chemistry, Chapter 27, 6th 7 27.2 Soap A mixture of sodium or potassium salts of long-chain fatty acids produced by alkaline hydrolysis (saponification) of animal fat with alkali
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Based on McMurry, Organic Chemistry, Chapter 27, 6th 8 Cleansing Action of Soap The carboxylate end of the long-chain molecule is ionic and therefore is preferentially dissolved in water The hydrocarbon tail is nonpolar and dissolves in grease and oil Soaps enable grease to be dissolved into water
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Based on McMurry, Organic Chemistry, Chapter 27, 6th 9 Detergents “Hard” water contains Mg +2 and Ca +2 that form insoluble salts with soaps Synthetic detergents are alkylbenzene sulfonates that dissolve dirt like soaps but do not form scums with Mg +2 and Ca +2 .
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Chapter27 - Chapter 27. Biomolecules: Lipids Based on...

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