POD13Key - Complete this mechanism by drawing curved arrows...

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Problem of the Day #13 – Answer Key Deadline : 3:00 p.m., Monday, 8/4/08 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 H O + H 3 C CH 3 O O + H 2 O H 3 O Under the acidic conditions employed, the enol form of the ketone will react with the conjugate acid of the aldehyde. These “starting materials” are shown below – you do not need to show how they are formed.
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Unformatted text preview: Complete this mechanism by drawing curved arrows to show movement of electron pairs, and by drawing structures for all important reaction intermediates. If an intermediate is a resonance hybrid, please draw only the MOST IMPORTANT contributing resonance structure. Remember, under acidic reaction conditions, all charged organic intermediates should be CATIONS ! H O H H 2 C CH 3 OH H O H H O H H H O H O O H H H O O H H O O H H H H O H O H H O H O H O H H...
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