14C_f10_finalB

14C_f10_finalB - Chemistry 14C Fall 2010 Final Exam Part B...

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Chemistry 14C Fall 2010 Final Exam Part B Page 1 Page 1 score = 1. (6) Acetaminophen is an analgesic (painkiller) found in several over-the-counter products such as Tylenol, Excedrin, Midol, Nyquil, and Sudafed. In the boxes below draw two additional resonance contributors for acetaminophen. Draw the most significant contributors possible; less significant contributors will earn less credit. Write "most significant" in the space below the most significant among the three contributors. N H O HO Acetaminophen 2. (2) Carefully circle all conjugated atoms. Do not circle any atoms that are not conjugated. N H O O H 3. (2) Complete this statement by writing a number in the blank. In its lowest energy conformation , __________ atoms of acetaminophen lie in the same plane. 4. (4) Circle the correct statements concerning the indicated bonds. N H O HO Bond A N H O HO Bond B Which bond is longer? Circle one: Bond A Bond B Bond lengths about equal Which bond has a higher barrier to rotation? Bond A Bond B Barriers to rotation about equal In the past, caffeine was added to acetaminophen pills. However, recent studies have shown that this drug combination carries up to three times the risk of liver toxicity than acetaminophen alone. N N N N CH 3 O CH 3 O CH 3 Caffeine 5. (4) Answer these questions concerning the structure of caffeine. (a) Write a number in the blank. Caffeine has __________ atoms with p orbitals. (b) Does caffeine obey Hückel's Rule? Circle one: Yes No (c) Is caffeine aromatic? Circle one: Yes No
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Chemistry 14C Fall 2010 Final Exam Part B Page 2 Page 2 score = 6. (2) Shown below are some possible products of caffeine metabolism. Circle the least likely metabolic product.
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14C_f10_finalB - Chemistry 14C Fall 2010 Final Exam Part B...

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