Lecture32-notes

Lecture32-notes - Reaction of carboxylic acids with thionyl...

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11/11/09 1 Reactions of Anhydrides Hydrolysis • In hydrolysis, an anhydride is cleaved to give two molecules of carboxylic acid: Reactions of Anhydrides Esterification (Alcoholysis) • Anhydrides react with alcohols to give one molecule of ester and one molecule of carboxylic acid—a useful method for the preparation of esters.
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11/11/09 2 Example of Esterification Preparation of aspirin: Reactions of Anhydrides Reaction with Ammonia and Amines – Formation of Amides • Anhydrides react with ammonia, as well as 1 o or 2 o amines, to form amides. • Note that two moles of amine are required (one forms the amide, the other acts as a base).
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11/11/09 3 Example of Amide Formation Preparation of acetamide Preparation of Acid Chlorides
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Unformatted text preview: Reaction of carboxylic acids with thionyl chloride: 11/11/09 4 Reactions of Acid Chlorides Hydrolysis Acid chlorides are cleaved by water to give a carboxylic acid and HCl: Reactions of Acid Chlorides Formation of esters Added amine base will precipitate HCl: 11/11/09 5 Reactions of Acid Chlorides Formation of amides: Reactions of Amides Hydrolysis Amides are relatively unreactive. They can be hydrolyzed with refluxing concentrated aqueous acid (e.g., HCl) or aqueous base (NaOH or KOH). 11/11/09 6 Amide Hydrolysis in Acid Base-Promoted Amide Hydrolysis 11/11/09 7 Some Important Amides Penicillin V Some Important Amides Lysergic acid diethyl amide (LSD)...
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Lecture32-notes - Reaction of carboxylic acids with thionyl...

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