HW13Key - In the first step of the mechanism, the conjugate...

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Bocknack CH 310M/318M Spring 2009 Graded Homework Problem #13 – Answer Key Deadline : 3:00 p.m., Monday, 4/6/09 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. Consider the overall transformation shown below: O CH 3 OH H 2 SO 4 (cat.) O O CH 3 (racemic) Propose a mechanism for this reaction. Use curved arrows to show movement of electron pairs, and be sure to draw structures of all important reaction intermediates. One of the important reaction intermediates is a resonance hybrid – please draw its two most important contributing resonance structures.
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Unformatted text preview: In the first step of the mechanism, the conjugate acid of CH 3 OH reacts with the alkene pi bond (the structures of the reactants involved in the first step are shown below the overall transformation). It is not necessary for you to show how CH 3 OH 2 + is produced via reaction of CH 3 OH with H 2 SO 4 . Since this reaction is acid-catalyzed, CH 3 OH 2 + should be produced as a product in the last step of your mechanism! O H O CH 3 H O CH 3 H (rearrangement) (LESS IMPORTANT) (MORE IMPORTANT) O CH 3 H O CH 3 H O O CH 3 H O CH 3 H O H H O H O H O O CH 3 H...
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This note was uploaded on 04/12/2009 for the course CH 53170 taught by Professor Bocknack during the Spring '09 term at University of Texas at Austin.

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