HW #14 Key - You may assume that H 2 O is present in large...

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Bocknack CH 310M/318M Fall 2008 Graded Homework Problem #14 – Answer Key Deadline : 3:00 p.m., Monday, 11/3/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. Propose a mechanism for the overall transformation given below. Used curved arrows to show movement of electron pairs , and be sure to draw structures for all important reaction intermediates. If an intermediate is a resonance hybrid, it is only necessary to draw the MOST IMPORTANT contributing resonance structure.
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Unformatted text preview: You may assume that H 2 O is present in large excess. To help you get started, the reactants involved in the first step of the mechanism are written below the overall transformation. Although the major organic product is formed as a racemic mixture, it is not necessary to show stereochemistry in your mechanism. H 2 O (large excess) O H Br Br O H Br Br O Br + Br + H 3 O O H Br Br O Br H H O H Br O Br Br H O H H...
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