HT1x-04 - H our Examination#1 Chemistry 302-302A March 1...

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Hour Examination #1, Chemistry 302-302A, March 1, 2004, 7:30-10:00 “Obscurity... is painful to the mind .... David Hume thanks to Susan M. Neider, former orgostudent 1 (16 points). Write arrow formalisms and provide detailed structures for the two unknown products. Be careful! O O heat + C 11 H 10 O 2 C 16 H 16 O 2 + 2 (10 points). Many, many attempts have been made to make adamantene, 1 . It is clear from the lack of success of most of these attempts that 1 is most unstable. Briefly show why. One attempt at making 1 , carried out in a small college town in New Jersey, involved a high-temperature elimination reaction and led not to 1 but to 2. Nonetheless, those who did the work were overjoyed by this result, as they thought it meant that their suggested route did indeed work. Explain. 1 2 3 (16 points). When tosylate 3 is treated with warm H 2 O/H 3 O + in the dark, many acyclic alcohols are formed. However, in addition there are cyclic products of the general structure 4 . Your job is to show the structure of the intermediate I , and predict
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