HT3-06.cwk - Hour Examination #3, Chemistry 302X - 2006...

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Hour Examination #3, Chemistry 302X - 2006 “Sometimes the straight and narrow path leads to a nasty place.” Alfred North Whitehead 1 (24 points). Here is a problem you have seen before. O COOEt CH 3 O COOEt CH 3 2. H 3 O + to pH = 7 1. HOEt/NaOEt 1 2 Amy Alonza Stagg suggests a simple S N 2 displacement of the methyl group by the ketone enolate to give, after protonation, 2 . O COOEt CH 3 O COOEt CH 3 H OH 2 O COOEt CH 3 2 S N 2 (a) For a start, criticize this seemingly almost trivial mechanism. Why can we be quite sure it s wrong? (b) Now, provide Amy with two alternative mechanisms. Hint: There are two archetypal reactions of carbonyl compounds in base. Each begins one of the possible mechanisms. (c) Finally, suggest an experiment that would tell which mechanism is operating. You may assume an ability to make any labeled compound necessary.
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2 (17 points). The following synthetic scheme was devised by Henry Gingrich s favorite student, I. B. Verständnislos. It contains several errors. Show what products really would be
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HT3-06.cwk - Hour Examination #3, Chemistry 302X - 2006...

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