HW14Key - If an intermediate is a resonance hybrid please...

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Bocknack CH 310M/318M Fall 2009 Graded Homework Problem #14 – Answer Key Deadline : 3:00 p.m., Monday, 11/2/09 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. When 3,3-dimethyl-1-butene is dissolved in CH 3 OH which contains a catalytic amount of H 2 SO 4 , a reaction occurs which yields 2-methoxy-2,3- dimethylbutane as the major product. This overall transformation is shown below: H 2 SO 4 (cat.) CH 3 OH OCH 3 In the space below, complete the mechanism of this reaction. Use curved arrows to show movement of electron pairs, and be sure to draw structures of all important reaction intermediates.
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Unformatted text preview: If an intermediate is a resonance hybrid, please draw all important contributing resonance structures. To help you get started, the reactants and curved arrows for the first step are given below. The conjugate acid of CH 3 OH acts as a catalyst in this reaction; for full credit your mechanism needs to show how this catalyst is regenerated. Since CH 3 OH is used as the solvent in this reaction, you may assume that it is present in large excess. CH 3 O H H H CH 3 O H methyl shift CH 3 O H O CH 3 H CH 3 O H OCH 3 CH 3 O H H...
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