CHEM 346 PROBLEM SET 1 Due 1 26 12 Please complete the following problems You may work either in groups or on your own The answer key will be posted on RamCT on the due date 1 Bruice Ch 15 problems 45 47 51 53 56 2 For problem 45 draw a mechanism for one nitration of the answer compound 3 For the following reaction one molecule of HBr was added Draw the product with an accompanying mechanism to explain its formation Explain the regioselectivity of the addition and rationalize why this reaction is so facile Hint resonance structures will help 4 Predict the major products of the following reactions HBr 1 equiv C D O O Cl AlCl3 O Cl AlCl3 Cl AlCl3 Cl AlCl3 A B 5 Describe each of the following transformations as an oxidation reduction or neither and explain your designation based on labeling the oxidation levels of the carbons involved in the transformation O OH O O H3C O H3C O H O O O O HO H H3C H3C A B C D E F O OH O O 6 Label each carbon on the following molecules with the appropriate oxidation level O O HO H O H O NH H N 9 deoxygelsemide 7 Bruice Ch 16 problem 44 CH3 CH3 NH O OH O epiquinamide berkeleyamide A
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