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problem set 2

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CHEM 313

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Chem 313 Problem Set #2, 2010 1. Using detailed mechanisms, explain how you can determine whether or not ester saponification happens through a tetrahedral intermediate (route A) or via aNdirect S 2 18 18 - mechanism (route B) using O labeled hydroxide ( OH ). route B O 18OH CH 3 O route A 2. Explain why acid catalyzed ester hydrolysis is reversible, but saponification is not. What conditions would you use to control the output of the acid catalyzed reaction? O O + H 3 /H2O H2O + CH 3 CH 3H + H O O O O OH /2 O CH 3 CH 3H + O O 3. Outline how you would prepare the following amino acids using the Gabriel synthesis: a. b. c. d. O O O O NH NH 2 NH 2 NH2 2 HO HO HO HO
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