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UK CHE 230 - CHE 230 - Organic Chemistry Exam 3

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1 CHE 230 - Organic Chemistry Exam 3, April 14, 2003 Name Student ID No. Before you begin this exam: First: You are allowed to have a simple model set at your seat. Please put away all other materials. Second: Place your student identification on your desk. A proctor will come around to check everyone’s ID. Third: Read through the entire exam. Your goal, as always, is to score as many points as possible. Do not waste time on problems that you can’t do if there are others that look easy. Fourth: It is critically important that your answers be written in a clear, unambiguous manner. Answers in which your intentions are unclear will not receive credit. Fifth: READ THE INSTRUCTIONS FOR EACH PROBLEM. You have until 9:50 to complete this exam. There will be no extensions, so budget your time carefully. Problem Points Score 1. 10 2. 5 3. 20 4. 30 5. 15 6. 5 7. 5 8. 10 Total 1002 1. In class we discussed the hydrogenation of the dehydrodecaline system below: HHH2, Pd/C a) (6 points) There are 2 diastereomers possible, but the only one that forms is the cis isomer shown. Is this reaction kinetic controlled or is it thermodynamic controlled? b) (4 points) Think about the difference between the catalyzed process and the uncatalyzed process. Does the catalyst change the ΔG for hydrogenation? YES or NO (Circle one) Does the catalyst change the ΔG‡ for hydrogenation? YES or NO (Circle one) 2. (5 points) Draw the expected major product resulting from addition of HBr to the enol ether shown. If you believe that a mixture of products will result, show each product. OHBr 3. (20 points) Provide the reagents needed for each of the transformations shown below. Please provide specific reagents (i.e. "HCl" rather than "acid" or "H+"). If more than one step is needed, show the reagents needed for each step. OHBrOHCNBr3 4. (30 points) Predict the product of the following reactions. You do not need to show mechanisms. In all cases the final product is a neutral compound. If you believe that no reaction will occur, write "no reaction." If the reaction shown proceeds with a specific stereochemical result, be sure to indicate the resulting stereochemistry. a) Cl tBuO K b) Br2 c) HCl d) H2, Pd/C e) 1. BH32. NaOH, H2O2 f) CF3CO3H4 5. a) (9 points) What reagents would bring about the transformation of 1 to make 2, and 2 to make 3? Write the required reagents in the space provided (note: if a 2-step procedure is needed, give the reagents for each step and be sure to indicate that you intend 2 separate steps and not a mixture of reagents). OH OHOHOHOTsABNaOHO1 2 34 Reagent(s) A = Reagent(s) B = b) (6 points) Draw a viable mechanism for the transformation of 3 into 4.5 6. (5 points) Propose a viable synthesis of the ether below, starting with any non-ether starting materials you wish. Only 1 or 2 steps is required. You do not need to show mechanisms, but be alert to conditions that favor substitution over elimination. OCH3CH3CH3 7. (5 points) Fill in the box with an appropriate starting material. Be sure that the compound you draw will be transformed to the product shown by treatment with the reagents given. OHCNMCPBAHHLiCN6 8. (10 points) Draw a viable mechanism for the following cyclization. Be sure to use the mechanism arrows carefully! HOOBrCCl4Br2 END OF EXAM7 SCRATCH


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UK CHE 230 - CHE 230 - Organic Chemistry Exam 3

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