POD09Key - important contributing resonance structures, not...

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Problem of the Day #09 – Answer Key Deadline : 3:00 p.m., Tuesday, 7/29/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. Consider the isomerization reaction shown below: 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 intermediate is a resonance hybrid, please write structures for all
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Unformatted text preview: important contributing resonance structures, not just the most important one! OH O H O H HO O O A proton on the α C atom is removed by the base toyield a resonance-stabilized enolate anion: Reprotonation then occurs on the γ C atom to yield the rearranged product. The "arrow pushing" is shown using the most important contributing resonance structure of the enolate anion: O O H OH O OH (cat.) H 2 O O...
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This note was uploaded on 09/14/2009 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas at Austin.

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