HW12Key - If an intermediate is a resonance hybrid, it is...

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Graded Homework Problem #12 – Answer Key Deadline : 3:00 p.m., Thursday, 3/27/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. Consider the overall transformation shown below, which is an example of a crossed aldol reaction: + O CH 3 H O H NaOH, H 2 O heat O + H 2 O Using curved arrows to show movement of electron pairs, propose a mechanism for the reaction shown above. As usual, be sure to show structures of all important reaction intermediates.
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Unformatted text preview: If an intermediate is a resonance hybrid, it is only necessary to draw the most important contributing resonance structure. Please note that this reaction takes place under basic reaction conditions all charged intermediates involved in the mechanism should therefore be anionic . H O H O O CH 2 H OH O (plus resonance) H O H O O H O H O O H OH H O O H (plus resonance) H O H OH...
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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 at Austin.

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