chemistry 242 exam 2 2008

chemistry 242 exam 2 2008 - CHEMISTRY 242 SECOND...

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CHEMISTRY 242 SECOND EXAMINATION Wednesday, October 22, 2008 Professor William P. Dailey KEY 1. (14 points ) Provide the product(s) and a complete arrow pushing mechanism for the following reaction. HNO 3 H 2 SO 4 (cat) CF 3 O N O O H O HO 3 S H O N O O H H N O O H 2 O CF 3 CF 3 H O 2 N CF 3 H O 2 N CF 3 H O 2 N H 2 O CF 3 O 2 N
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2 2. (14 Points) The rate of reaction between methylamine and acetone to yield the corresponding imine depends greatly on the pH of the solution. Graphically depict how the rate of imine formation varies with pH of the reaction medium. Write the complete mechanism for the reaction and justify your graph on the basis of this mechanism. H 3 C CH 3 O NH 2 various pH H 3 C CH 3 N CH 3 H 3 C H 3 C CH 3 O H O H H H 3 C CH 3 O H H 2 N CH 3 H 3 C CH 3 N OH H H H 3 C CH 3 HN OH 2 N H H O H H 3 C CH 3 N CH 3 If too basic, then the carbinolamine can't be protonated and eliminate water. H
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chemistry 242 exam 2 2008 - CHEMISTRY 242 SECOND...

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