HW08 - IF A REACTION INTERMEDIATE IS A RESONANCE HYBRID,...

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CH 310N Spring 2008 Last Name: First Name: Dr. Bocknack UTEID: Score: Graded Homework Problem #08 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.
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Unformatted text preview: IF 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....
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This note was uploaded on 09/04/2008 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas at Austin.

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