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POD12Key - contributing resonance structure You may assume...

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Problem of the Day #12 – Answer Key Deadline : 3:00 p.m., Friday, 8/1/08 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 illustrates the acid-catalyzed hydration reaction of an amide: H 3 C N CH 3 O CH 3 + H 2 O (large excess) H 2 SO 4 Δ H 3 C OH O + H 2 N(CH 3 ) 2 Using curved arrows to show movement of electron pairs, propose a mechanism for the acid-catalyzed amide hydrolysis reaction shown above. As usual, be sure to show structures of all important reaction intermediates. If an intermediate is a resonance hybrid, it is only necessary to draw the most important
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Unformatted text preview: contributing resonance structure. You may assume that hydronium (H 3 O + ) is the acidic species that reacts with the amide in the first step of the mechanism – it is not necessary to show how H 3 O + is generated under the given reaction conditions. H 3 C N CH 3 O CH 3 H O H H H 3 C N CH 3 O CH 3 H H O H H 3 C N CH 3 O CH 3 O H H H H O H H 3 C N CH 3 O CH 3 O H H H O H H H 3 C N CH 3 O H 3 C O H H H H O H H 3 C OH O H CH 3 N H CH 3 H 3 C OH O CH 3 N H CH 3 H (+ resonance) (+ resonance)...
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