CH19 April 11 - Hydrolysis: Mechanism: React with H 2O to...

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Formation of Acid Anhydrides from Carboxylic Acids Examples: Two moles of carboxylic acids are heated together to eliminate 1 mole of H 2O This is a difficult procedure. Acetic anhydride is the only anhydride commonly produced Cyclic anhydrides are commonly produced when 5/6 membered rings can be formed from the dehydration of a diacid Title: Jul 25 ­ 8:56 AM (1 of 8)
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Fischer Esterification Reaction Mechanism: Formation of Esters from Carboxylic Acids SN2 reaction of a carboxylate anion with a 1 oalkyl halide Fischer Esterification: Nucleophilic acyl substitution of a carboxylic acid with an alcohol Title: Jul 25 ­ 9:00 AM (2 of 8)
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Formation of Amides from Carboxylic Acids General Reaction: This is a very difficult transformation to accomplish. Why? Reaction with DCC: Title: Jul 25 ­ 9:03 AM (3 of 8)
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Preparation and Reactivity of Acyl Halides Preparation: Previously Encountered Reaction: Friedel­Crafts Acylation Title: Jul 25 ­ 9:04 AM (4 of 8)
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Reactions of Acyl Halides
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Unformatted text preview: Hydrolysis: Mechanism: React with H 2O to yield carboxylic acids Generates HX, a mild base is added to neutralize the reaction (pH = 7) Title: Jul 26 ­ 8:44 AM (5 of 8) Reactions of Acyl Halides (cont'd) Formation of Esters: Examples: Acid Halides + alcohols with pyridine (or mild NaOH) Less hindered alcohol groups are more reactive (1 o>2o>3o) Allows for selective synthesis when 2 alcohol groups are present The mechanism is identical to hydrolysis. The only difference is the alcohol used: Title: Jul 26 ­ 8:44 AM (6 of 8) Reactions of Acyl Halides (cont'd) Aminolysis: Examples: React with NH 3, 1oand 2oamines HCl is neutralized by a second equivalent of amine or an added base Title: Jul 26 ­ 8:44 AM (7 of 8) Reactions of Acyl Halides (cont'd) Reduction: Turning Acid Chlorides into Alcohols Example: Reaction Mechanism: LiAlH4reduces acid halides to aldehydes and then to 1 oalcohols Title: Jul 26 ­ 8:44 AM (8 of 8)...
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This note was uploaded on 05/08/2008 for the course CHEM 2212 taught by Professor Habbard during the Spring '08 term at University of Georgia Athens.

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CH19 April 11 - Hydrolysis: Mechanism: React with H 2O to...

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