HW13Key - mechanism, the conjugate acid of CH 3 OH reacts...

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Graded Homework Problem #13 – Answer Key Deadline : 3:00 p.m., Monday, 3/31/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. Propose a mechanism to account for the overall transformation given below. Use curved arrows to show movement of electron pairs, and draw structures for all important reaction intermediates. One of the important reaction intermediates is a resonance hybrid – please draw its two most important contributing resonance structures. In the first step of the
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Unformatted text preview: mechanism, the conjugate acid of CH 3 OH reacts with the alkene pi bond (the structures of the reactants involved in the first step are shown below the overall transformation). It is not necessary for you to show how CH 3 OH 2 + is produced via reaction of CH 3 OH with H 2 SO 4 . Since this reaction is acid-catalyzed, CH 3 OH 2 + should be produced as a product in the last step of your mechanism! O CH 3 OH H 2 SO 4 (cat.) O OCH 3 O H O CH 3 H O H O CH 3 H O H O O CH 3 H O CH 3 H O O CH 3 H O CH 3 H...
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