HW14Key - CH 3 H Br Br CH 3 OH (solvent) OCH 3 H CH 3 Br Br...

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Graded Homework Problem #14 – Answer Key Deadline : 3:00 p.m., Thursday, 4/3/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. A haloether is an organic compound which has a halogen atom (X) and an alkoxy group (OR) as substituents on adjacent carbon atoms. Haloethers can be conveniently prepared via reaction of an alkene with X 2 in the presence of an alcohol (ROH) as solvent. A specific example is shown below. Note that the product formed in this reaction is racemic – the structure of only one enantiomer is written below.
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Unformatted text preview: CH 3 H Br Br CH 3 OH (solvent) OCH 3 H CH 3 Br Br CH 3 OH 2 In the space below, propose a mechanism for the overall transformation given above. Use curved arrows to show movement of electron pairs, and draw structures of all important reaction intermediates. Show all lone pairs and nonzero formal charges! If a reaction intermediate is a resonance hybrid, it is only necessary to draw the most important contributing resonance structure. (racemic) CH 3 H Br Br Br CH 3 H Br O CH 3 H O H Br CH 3 H 3 C H O CH 3 H OCH 3 H Br CH 3 O CH 3 H H...
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