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HW05 - Use curved arrows to show movement of pairs of...

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CH 310N Spring 2008 Last Name: First Name: Dr. Bocknack UTEID: Score: Graded Homework Problem #05 Deadline : 3:00 p.m., Monday, 2/11/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. When the geminal diol shown below is heated in water containing a catalytic amount of sulfuric acid, a reaction occurs which produces water and cyclohexanone as the major products: O H OH H 2 SO 4 (cat.), H 2 O (solvent) O + O H 2 Propose a mechanism to account for this overall transformation.
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Unformatted text preview: 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, it is only necessary to draw the most important contributing resonance structure. You may assume that hydronium (H3O+) is present under the given reaction conditions. (Hint : The mechanism of acid-catalyzed ketone hydration that we discussed in lecture is reversible .)...
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