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HW13Key - Use curved arrows to show movement of electron...

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Bocknack CH 310M/318M Fall 2009 Graded Homework Problem #13 – Answer Key Deadline : 3:00 p.m., Thursday, 10/29/09 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. (a) (5 points) When methylenecyclopentane is exposed to HCl, a single, achiral product is formed. Please draw the structure of this product in the empty box below. (b) (15 points) In the space below, propose a mechanism for the reaction described above.
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Unformatted text preview: Use 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, please draw all important contributing resonance structures. For full credit, your mechanism needs to be consistent with the product you drew in your answer for Part (a)! HCl Cl CH 3 H Cl H Cl Cl CH 3...
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