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HW18Key - resonance structures for an aromatic ring however...

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CH 310N Spring 2008 Last Name: First Name: Dr. Bocknack UTEID: Score: Graded Homework Problem #18 – Answer Key Deadline : 3:00 p.m., Thursday, 4/24/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth 20 raw points. Propose a mechanism to account for the overall transformation shown below. As usual, use curved arrows to show movement of electron pairs, and be sure to draw structures of all important reaction intermediates. If an intermediate is a resonance hybrid, please draw all of the important contributing resonance structures!!! It is not necessary to draw both
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Unformatted text preview: resonance structures for an aromatic ring, however. Note that this reaction occurs under acidic conditions, so any charged intermediates should be cationic!!! [Hint : The first step of the mechanism involves a Bronsted-Lowry acid-base reaction.] CH 3 CH 3 HO CH 3 H 3 O + (cat.) heat CH 3 H 3 C CH 3 + H 2 O CH 3 CH 3 HO CH 3 CH 3 H 3 C CH 3 H O H H CH 3 CH 3 O CH 3 H H CH 3 CH 3 CH 3 O H H H CH 3 H 3 C CH 3 O H H H CH 3 H 3 C CH 3 H CH 3 H 3 C CH 3 H (resonance-stabilized carbocation intermediate) O H H H O H H...
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