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POD13Key - As usual be sure to show structures of all...

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Problem of the Day #13 Answer Key Deadline : IN CLASS on M 8/2/2010 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.) 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.
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Unformatted text preview: 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. OCH 2 CH 3 O OH O CH 3 CH 2 OH H O H H OCH 2 CH 3 O H O H H (plus resonance) OCH 2 CH 3 HO O H H O H H OCH 2 CH 3 HO OH H O H H HO OH O H CH 2 CH 3 O H H OH O H O H H (plus resonance) H O H H...
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