HW14 - Note that the product formed in this reaction is...

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CH 310M/318M Spring 2008 Last Name: First Name: Dr. Bocknack UTEID: Score: Please circle the section in which you are registered ! POINTS MAY BE DEDUCTED IF YOU DON’T ! MWF 9:00 TTh 8:00 Graded Homework Problem #14 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.
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Unformatted text preview: Note that the product formed in this reaction is racemic – the structure of only one enantiomer is written below. 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)...
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