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Course: CH 310N, Spring 2007School: University of Texas
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Homework Graded Problem #08 Answer Key Deadline: 3:00 p.m., Thursday, 2/28/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. Consider the overall transformation shown below: O Br K OC(CH3)3 O benzene (solvent) + HOC(CH3)3 + K Br Propose a mechanism for this overall transformation. Use curved arrows to show movement of pairs of electrons, and be sure to draw...
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Homework Graded Problem #08 Answer Key
Deadline: 3:00 p.m., Thursday, 2/28/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!!
This problem is worth a total of 20 raw points. Consider the overall transformation shown below:
O Br K OC(CH3)3
O
benzene (solvent)
+
HOC(CH3)3
+
K
Br
Propose a mechanism for this overall transformation. Use curved arrows to show movement of pairs of electrons, and be sure to draw structures of all important reaction IF intermediates. A REACTION INTERMEDIATE IS A RESONANCE HYBRID, PLEASE DRAW ALL IMPORTANT CONTRIBUTING RESONANCE STRUCTURES!!!. Please note that the tert-butoxide anion is a strong base, and that a new carbon-carbon bond is formed at the alpha position of the ketone starting material. The benzene solvent does not participate in the reaction in any way.
OC(CH3)3 O H Br O
HOC(CH3)3 O Br Br
(resonance-stabilized enolate anion)
O Br
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