2003 Organic Chemistry CHE230-001 EXAM3 Page 1 of 6 Cover Sheet! EXAM3 CHEM230-001 FALL 2003 PRINT your name legibly on the line below. _____________________________________________________2003 Organic Chemistry CHE230-001 EXAM3 Page 2 of 6 Name: ______________________ Student ID No:____________ First: You are allowed to have a writing utensil, a calculator and molecular 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. Is your name and number on your test? Third: Quickly 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 easy questions to do first. Fourth: It is critically important that your answers be written in a clear, unambiguous manner. Answers in which your intentions are unclear may not receive credit. SHOW YOUR WORK! Fifth: READ THE INSTRUCTIONS FOR EACH PROBLEM. answer each question Problem Number Points possible Score 1a. 15 _____ 1b. 15 _____ 2. 20 _____ 3. 10 _____ 4. 10 _____ 5. 10 _____ 6. 10 _____ 7. 10 _____ 8. above and beyond 5 _____ 9. above and beyond 5 _____ ------------------------------------------------------------------------------------- Total 100 _____2003 Organic Chemistry CHE230-001 EXAM3 Page 3 of 6 1. Predict the products. The double bonds in the benzene rings of 1A do not react under these conditions. a. (10 pts.) b. (10 pts.) c. (10 pts.) You can draw this structure as:PhPh1A1A1) BH3, ether, 25 °C2) H2O2, NaOH, H2Omy answer for prob.1a1A1) HCl, solventmy answer for prob.1bcarbon skeleton rearrangesto alleviate ring strainDraw one ofthe two diastereomers1A1) solventmy answer for prob.1cOOHO FFF2003 Organic Chemistry CHE230-001 EXAM3 Page 4 of 6 HSO3CF3+CHCH3CH3CHCH3CH3SO3CF3SO3CF3CH3CH3HSO3CF3+2A2B2C 2D 2. Consider the molecules in 2A-2D and the energy diagram above. a. (16 pts.) Put the letters in the label boxes on the diagram. There are more labels than there are molecules. You should NOT fill in ALL the boxes with numbers! b. (4 pts) HSO3CF3 is a (circle one!) initiator, transition state, conformer, catalyst, intermediate, diastereomer, proton acceptor, a piece of poop, tautomer, base. 3. (10 pts.) Circle the most stable cation. Draw an X over the least stable cation. a. (5 pts.) Briefly explain your choice of the most stable carbocation. ______________________________________________________________ ______________________________________________________________ ______________________________________________________________ ∆GReaction progressNCOCCCCl3A3B3C3DCCl3ECl2003 Organic Chemistry CHE230-001 EXAM3 Page 5 of 6 4. (10 pts.) Predict the major product of the following reaction. Be careful. Show stereochemistry. 5. (10 pts.) Devise a synthesis of 5B from alkyne 5A. Pay attention to stereochemistry. Draw chemical reactions in the box below at right. 6. (10 pts) Why does the alkene react with acid, whereas the alkane does not? Be as brief as possible. You might want to draw a molecular orbital energy diagram in the margin at left if you can’t put this into words. __________________________________ _____________________________________ _____________________________________ 7. (10 pts.) What is the oxidation of Os in 7A? ___ What is the oxidation of Os in 7B? ____ OsOOOOOsOOOO+7A7B7C 8. (5 pts.) How would you make 5A with starting materials possessing no more than 5 carbon atoms? Draw a chemical reaction below at left. 9. (5 pts.) Think about the reaction of 7C with ozone followed by oxidizing conditions. Draw the product below at right. 8 9 Br2 CCl4 (solvent)my answer to prob. 4OBrBrHHO5A5BMy answer to
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