HWKey (1) - (each having only one atom with a nonzero...

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Problem of the Day #20 – Answer Key Deadline : 4:00 p.m., Thursday, 7/10/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. Consider the overall transformation shown below, which is an example of an acid-catalyzed alcohol dehydration reaction: Note that a molecule of water forms as a product in this reaction. Water is also used as the solvent. The mechanism of this reaction is outlined below. Complete this mechanism by filling in the structures of the missing intermediates. Use normal curved arrows to show how pairs of electrons move in each step. You DO NOT have to concern yourself with stereochemistry in writing your mechanism. Note that one of the key intermediates is a resonance hybrid, which has two important contributing resonance structures
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Unformatted text preview: (each having only one atom with a nonzero formal charge). Draw the resonance structure indicated in the appropriate box. You DO NOT need to draw curved arrows to show how one resonance structure is converted into the other resonance structure! CH 3 CH 3 OH OH H 3 O + (cat.) H 2 O (solvent) + H 2 O CH 3 CH 3 O H O H H O H H + H 2 O (rearrangement) O H H H O H H CH 3 CH 3 OH OH LESS IMPORTANT RESONANCE STRUCTURE MORE IMPORTANT RESONANCE STRUCTURE CH 3 CH 3 O (Draw curved arrows to show how H 2 O reacts with the MORE IMPORTANT resonance structure) CH 3 CH 3 OH O H H CH 3 CH 3 OH CH 3 O CH 3 H CH 3 O CH 3 H...
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