HW11 - OH O + CH 3 CH 2 OH Using curved arrows to show...

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CH 310N Spring 2008 Last Name: First Name: Dr. Bocknack UTEID: Score: Graded Homework Problem #11 Deadline : 3:00 p.m., Monday, 3/17/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. Fischer esterification (acid-catalyzed esterification of a carboxylic acid) is reversible . The reverse of Fischer esterification is called acid-catalyzed ester hydrolysis . In the acid-catalyzed hydrolysis of an ester, the ester is exposed to aqueous acid, yielding a carboxylic acid and an alcohol as products. A specific example is shown below: OCH 2 CH 3 O + H 2 O H 2 SO 4 (cat.)
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Unformatted text preview: OH O + CH 3 CH 2 OH Using curved arrows to show movement of electron pairs, propose a mechanism for the acid-catalyzed ester hydrolysis reaction shown above. As usual, be sure to show structures of all important reaction intermediates. If an intermediate is a resonance hybrid, it is only necessary to draw the most important contributing resonance structure. You may assume that hydronium (H 3 O + ) is the acidic species that reacts with the ester it is not necessary to show how H 3 O + is generated under the given reaction conditions....
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This note was uploaded on 09/04/2008 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas at Austin.

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