chapter21_part2

chapter21_part2 - Chapter 21 Carboxylic Acid...

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Chapter 21 Carboxylic Acid Derivatives (continued)
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Chapter 21 2 Hydrolysis of Acid Chlorides and Anhydrides Hydrolysis occurs quickly, even in moist air with no acid or base catalyst. Reagents must be protected from moisture. =>
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Chapter 21 3 Acid Hydrolysis of Esters Reverse of Fischer esterification. Reaches equilibrium. Use a large excess of water. + CH 3 C O OCH 3 HOH CH 3 C O OH + CH 3 OH H + =>
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Chapter 21 4 Saponification Base-catalyzed hydrolysis of ester. “Saponification” means “soap-making.” Soaps are made by heating NaOH or KOH (lye) with a fat (triester of glycerol) to produce the sodium salt of a fatty acid - a soap O O O O O O animal fat KOH H 2 O 3 O O _ K + lye soap
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Chapter 21 5 Foreshadowing… Soaps and detergents work by creating “micelles” – the hydrophobic tails ball up, revealing a hydrophilic surface Dirt (insoluble in water) gets “dissolved inside the micelle, which is soluble in water
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Chapter 21 6 Soaps and Detergents Soaps form water-insoluble salts when used in water containing Ca(II), Mg(II), and Fe(III) ions ( hard water hard water ) + + A sodium soap (soluble in water as micelles) Calcium salt of a fatty acid (insoluble in water) 2 CH 3 ( CH 2 ) 1 4 COO -  Na + Ca 2 + [ CH 3 ( CH 2 ) 1 4 COO - ] 2 Ca 2 + 2 Na + Sulphate and phosphate detergents don’t precipitate with these metals, so are more commonly utilized (see your shampoo bottle)
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Chapter 21 7 Hydrolysis of Amides Prolonged heating in 6 M HCl or 40% aqueous NaOH is required.
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