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Graded Homework 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 benzene (solvent) K OC(CH 3 ) 3 O + HOC(CH 3 ) 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 intermediates. IF A REACTION
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Unformatted text preview: 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. O Br H HOC(CH 3 ) 3 Br OC(CH 3 ) 3 O Br O Br (resonance-stabilized enolate anion) O...
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This note was uploaded on 04/30/2008 for the course PHY 317L taught by Professor Ritchie/lang during the Fall '08 term at University of Texas.

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