POD18 - One of these resonance structures is relatively...

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CH s310N/s318N Summer 2008 Last Name: First Name: Dr. Bocknack UTEID: Score: Problem of the Day #18 Deadline : 3:00 p.m., Wednesday, 8/13/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. When 1,3,5-hexatriene is exposed to one equivalent of HBr, an addition reaction occurs which produces a mixture of three different constitutional isomers. The reaction mechanism is outlined below. The intermediate that is formed in the first step is a resonance hybrid. Draw the three important contributing resonance structures, one per box.
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Unformatted text preview: One of these resonance structures is relatively less important than the other two – indicate which one by marking the box labeled “LEAST IMPORTANT” with the symbol “X”. Draw the addition product that arises due to each resonance structure in the “PRODUCT” box beneath it. Identify the “KINETIC PRODUCT” by writing the letter “K” in the small box below it. Identify the “THERMODYNAMIC PRODUCT” by writing the letter “T” in the small box below it. H Br LEAST IMPORTANT LEAST IMPORTANT LEAST IMPORTANT PRODUCTS: Br Br Br...
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This note was uploaded on 09/14/2009 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas.

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