Wake Forest University Chemistry Exam 3 - Organic Chemistry - Prof. Paul Jones, Exams of Organic Chemistry

Download Wake Forest University Chemistry Exam 3 - Organic Chemistry - Prof. Paul Jones and more Exams Organic Chemistry in PDF only on Docsity! Exam 3 Name:_____________________________ April 23, 2002 I agree to observe the Wake Forest Chm 122 Honor Code during this exam. 60 minutes 100 points Instructions: There are eleven questions and one bonus on the following pages. Check the exam now to be sure that you have eleven questions and the bonus. There are two blank pages to be used as scratch paper at the end of the exam. You may remove these pages, as needed, but all answers must appear on the same page as the question and, where appropriate, in the designated space. Write your name, clearly, in the space provided above. Questions may contain several parts. Be sure to completely read each question so that you answer all parts! Work 1-11 to the best of your ability before attempting the bonus. Do not hesitate to ask a question if it arises. Clearly answer each question - if it is unclear what you intended to answer, the problem will be counted wrong. You have sixty minutes to complete the exam. I advise that you work through the exam once answering what you know and save problems you are unsure of for the end of the period. Exams will be collected, promptly, sixty minutes after they are distributed. You are expected to abide by the Wake Forest University Honor Code and the rules of decency. Any violations of the Honor Code will be pursued through all necessary means. Good luck. 1. Draw the structure of m-chlorophenol. 3 points OH Cl 2. Draw 3,5-dibromoaniline. 3 points Br BrH2N 3. Draw the most stable resonance structure of naphthalene. If the structure shown is the one, circle the molecule. 3 points 4. Circle any aromatic molecules in the following list: 6 points N H H 7. continued C C Na, NH3 not applicable Cl O AlCl3 O C C H2, Lindlar's Catalyst not applicable Cl Br2 FeBr3 Cl Br OCH3 H2SO4 OCH3 8. In each pair, circle the faster reaction. 10 points NC 50 oC CN NC 50 oC CN CN CN NC 50 oC CN NC 50 oC CN O NC 50 oC CN NC 50 oC CN NC 50 oC CN NC 100 oC CN O 9. Draw the mechanism for the following transformation: 10 points OH H2O H2SO4 O See notes 10. When pure A is treated with aqueous sulfuric acid, a mixture of A and B results. An identical mixture is obtained when pure B is treated in the same fashion. Explain. 10 points OH H2O H2SO4 OH OH H2O H2SO4 OH OHOH A B A A B B See notes – this was on an earlier problem set.