HW06Key - If a reaction intermediate is a resonance hybrid...

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Graded Homework Problem #06 – Answer Key Deadline : 3:00 p.m., Thursday, 2/21/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. When the cyclic acetal shown below is heated in water containing a catalytic amount of sulfuric acid, a hydrolysis reaction occurs which produces methanol and the acyclic product shown: O OCH 3 + H 2 O H 2 SO 4 (cat.) HO H O + CH 3 OH Propose a mechanism for this overall transformation. Use curved arrows to show movement of pairs of electrons, and be sure to draw structures of all important reaction intermediates.
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Unformatted text preview: If a reaction intermediate is a resonance hybrid, it is only necessary to draw the most important contributing resonance structure. You may assume that the hydronium ion, H 3 O+, is the acidic species that will react with the acetal. You do not need to show how H 3 O + is formed. (Hint : Remember that the mechanism of acetal formation that we discussed in lecture is reversible.) O OCH 3 HO H O CH 3 OH O H H H O OCH 3 H O H H O O H H (plus resonance) O O H H O H H O OH O H H H O OH H O H H H (plus resonance) O H H HO H O O H H H...
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