Cover Sheet! EXAM 4 || Final Exam CHEM230-001 Spring 2006 PRINT your name legibly on the line below. PRINT your student id number on the line below.2006 Organic Chemistry CHE230-001 EXAM 4 Name: _______________________________ Student ID No:_____________________ Place your student identification on your desk. A proctor will come around to check your ID. Put your name and number on your test? 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! Problem Number Points possible Score 1. 10 _____ 2. 20 _____ 3. 15 _____ 4. 20 _____ 5. 20 _____ 6. 15 _____ 7. 10 _____ 8. 20 _____ 9. 15 _____ 10. 20 _____ 11. 15 _____ 12. 10 _____ 13. 10 _____ ----------------------------------------------------------------------------------------------- Total 200 _____2005 8-week summer Organic Chemistry CHE230-001 EXAM 3 page 1/4 1. Problem 1aNNHHHHHHHHHHHHProblem 1b a. (5 pts.) This is a neutral species. There are some electrons missing (nothing else is missing). Put the missing electrons on the structure to complete the structure. (Hint: computing the degrees of unsaturation might help.) b. (5 pts.) Above, draw a charge separated resonance structure of your complete Lewis structure of 1a. 2. Consider molecular formula: C14H4Cl10. a. (10 pts.) Compute the degrees of unsaturation. ____________________________________________________________________________ ____________________________________________________________________________ ____________________________________________________________________________ b. (10 pts.) There is one ring in the structure. Could the structure possibly be aromatic? ____________________________________________________________________________ ____________________________________________________________________________ 3. (15 pts.) How are these two molecules related to each other? Do they have the same physical properties? ClCl2005 8-week summer Organic Chemistry CHE230-001 EXAM 3 page 2/4 4. Consider the molecule below. a. (10 pts.) Circle the weakest C-C bond in structure 4A below. 4A b. (10 pts.) At right above, draw a product of molecule 4A and NOOBrhv 5. Consider molecule 5A. a. (10 pts.) Below, draw the enantiomer of molecule 5A. Count the carbon atoms in your structure! 5AClHHH b. (10 pts.) Name 5A as a cyclohexane derivative. Stereochemistry! ____________________________________________________________________________ ____________________________________________________________________________2005 8-week summer Organic Chemistry CHE230-001 EXAM 3 page 3/4 6. (15 pts.) Draw the Diels –Alder product of O+CN Count your carbon atoms. Stereochemistry is important. 7. 7A 7B a. (5 pts.) How many 13C NMR in 7A. ____ b. (5 pts.) How many 13C NMR in 7B. ____ 8. (20 pts.) Draw the two highest-energy occupied molecular orbitals in 1,3-butadiene. Same question: draw only the occupied pi molecular orbitals of 1,3-butadiene. 9. (15pts.) Draw the product. HOOFOFF2005 8-week summer Organic Chemistry CHE230-001 EXAM 3 page 4/4 10. (20 pts.) Consider the reaction energy diagrams below. Use each letter only once. Rxn CoordinateRxn CoordinateRxn CoordinateRxn CoordinateRxn CoordinateRxn CoordinateABCDEF a. The diagram of the fastest reaction is __________ . b. The diagram that might represent the conversion of one enantiomer into another is __________ . c. The diagram that represents an endothermic reaction with one intermediate is __________ . d. The diagram that represents the twisting of a double bond through a dihedral angle of 180° starting from a cis-alkene and producing a trans-alkene is __________ . 11. (15 pts.) Predict the product. 1) (CH3CH2)2BH2) H2O2, NaOH(aq)Ether (solvent)Problem 112005 8-week summer Organic Chemistry CHE230-001 EXAM 3 page 5/4 12. (10 pts.) Predict the product. 1) O32) H2O2, NaOH(aq)Ether (solvent)Problem 12 13. (10 pts.) Predict the product. 1) H3O(+)HeatwaterProblem
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