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POD19Key - It is not necessary to draw both resonance...

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Problem of the Day #19 – Answer Key Deadline : 3:00 p.m., Thursday, 8/14/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth 20 raw points. Propose a mechanism to account for the overall transformation shown below. As usual, use curved arrows to show movement of electron pairs, and be sure to draw structures of all important reaction intermediates. If an intermediate is a resonance hybrid, please draw all of the important contributing resonance structures!!!
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Unformatted text preview: It is not necessary to draw both resonance structures for an aromatic ring, however. Note that this reaction occurs under acidic conditions, so any charged intermediates should be cationic!!! You may assume that hydronium (H 3 O + ) is present under the given reaction conditions – you do not need to show how H 3 O + is formed. H 2 O H 2 SO 4 (cat.) H O H H H H O H H H H H O H H O H H...
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