HW15Key - Graded Homework Assignment #15 Answer Key...

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Graded Homework Assignment #15 – Answer Key Deadline : 9:00 a.m., Friday, 4/9/10 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This assignment is worth a total of 40 raw points. 1. (20 points) Consider the overall transformation shown below. The major product is formed as a racemic mixture of enantiomers. Stereochemistry is NOT shown in the structure given. 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. It is not necessary to show stereochemistry in any structures that you draw. Be sure to show all lone pairs and all nonzero formal charges in all structures that you draw, however! One of the important reaction intermediates is a resonance hybrid – please draw its two most important contributing resonance structures. 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
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HW15Key - Graded Homework Assignment #15 Answer Key...

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