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HW19TTh - Br CH 3 OH(solvent Δ OCH 3 CH 3 OH 2 Br(racemic...

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TTh 12:30 Section – Bocknack CH 310M/318M Fall 2008 UTEID: Please submit to the correct slot in the collection box outside WEL 2.212!!! Last Name: First Name: Score: Graded Homework Problem #19 Deadline : 3:00 p.m., Monday, 12/1/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. When (1-bromomethyl)cyclohexene is dissolved in methanol and the solution is heated, one of the products isolated is 1-methylene-2-methoxycyclohexane (as a racemic mixture). This overall transformation is shown below:
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Unformatted text preview: Br CH 3 OH (solvent) Δ OCH 3 + CH 3 OH 2 + Br (racemic) In the space below, propose a mechanism to account for this reaction. Use curved arrows to show movement of electron pairs, and draw structures of all important reaction intermediates. If an intermediate is a resonance hybrid, please draw ALL IMPORTANT contributing resonance structures. Although the product shown is formed as a racemic mixture, it is not necessary to show stereochemistry in your mechanism....
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