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HW16Key - It is not necessary to provide an explanation...

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Graded Homework Problem #16 – Answer Key Deadline : 3:00 p.m., Thursday, 4/10/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. When 1,3-butadiene is treated with Cl 2 in CH 3 OH solvent, a mixture of isomeric products is isolated. The overall transformation and the relative amount of each constitutional isomer formed as a result of the reaction are shown below: + Cl Cl CH 3 OH Cl OCH 3 (30%; mixture of E and Z ) + OCH 3 Cl (70%; racemic) (a) (4 points) Does this reaction take place under kinetic control or thermodynamic control. Circle your response below.
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Unformatted text preview: It is not necessary to provide an explanation. KINETIC CONTROL THERMODYNAMIC CONTROL (b) (16 points) Propose a mechanism which accounts for formation of both products. 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 of the important contributing resonance structures!!! Cl Cl Cl Cl Cl (resonance-stabilized allylic carbocation) CH 3 OH CH 3 OH Cl O H CH 3 CH 3 OH OCH 3 Cl CH 3 OH 2 Cl O H CH 3 CH 3 OH Cl OCH 3 CH 3 OH 2...
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