HW19Key - Be sure to show lone pairs and nonzero formal...

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Bocknack CH 310M/318M Fall 2009 Graded Homework Problem #19 – Answer Key Deadline : 3:00 p.m., Monday, 11/30/09 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. When 1-bromomethylcyclohexene is heated in ethanol, several products are isolated. One of these products is 3-methylenecyclohexene. This overall transformation is shown below: Br CH 3 CH 2 OH Δ + CH 3 CH 2 OH 2 + Br + other products (a) (16 points) In the space below, 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.
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Unformatted text preview: Be sure to show lone pairs and nonzero formal charges! If an intermediate is a resonance hybrid, please draw all important contributing resonance structures. (b) (4 points) Which mechanism from Chapter 9 best describes how the transformation shown above comes about? Circle your choice below. No further explanation is required. For credit, the answer that you circle needs to be consistent with your proposed mechanism! S N 1 S N 2 E1 E2 Br H Br (resonance-stabilized carbocation) H O CH 2 CH 3 H O CH 2 CH 3 H...
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This note was uploaded on 04/09/2010 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas.

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