Lecture23outline-1

Lecture23outline-1 - I. Review In the presence of base and...

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I. Review • In the presence of base and alcohol, carboxylic acids only undergo deprotonation and do not react further • In the presence of acid and alcohol, carboxylic acids are activated toward nucleophilic attack that leads to a tetrahedral intermediate that ultimately yields an ester (Fischer esterification) • Esters and acids are similar thermodynamically, so esters can be hydrolyzed to acids in the presence of water • The mechanism of this reaction is exactly the reverse of the mechanism for esterification • When hydroxy groups are in the same molecule as a carboxylic acid, strong acid catalyzes intramolecular nucleophilic addition to form cyclic esters called lactones • Amines react with carboxylic acids to form ammonium carboxylates that leave behind small concentrations of the reactants • Due to the low concentrations of the reactive species, amide formation from amines and acids requires heating • Acid chlorides can be formed by heating carboxylic acids with SOCl
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This note was uploaded on 05/17/2010 for the course CHEM 0740 taught by Professor Professor during the Spring '10 term at Pittsburgh.

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Lecture23outline-1 - I. Review In the presence of base and...

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