practice final exam - Chem. 310N, Spring 2008, Professor...

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Chem. 310N, Spring 2008, Professor Krische Final Exam Key Last Name: First Name: Problem 1. (30 points) 2. (12 points) 3. (10 points) 4. (14 points) 5. (15 points) 6. (10 points) 7. (24 points) 8. (20 points) 9. (15 points) Total Points: /150 Letter Grade T-Score A+ 100-96 A 95-92 A- 91-90 B+ 89-86 B 85-82 B- 81-80 C+ 79-76 C 75-72 C- 71-70 D+ 69-66 D 65-62 D- 61-60 F 60-0
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1. (30 Points) For the following compounds, circle the one that embodies the indicated property. (2 pts each) a. Retains deuterium upon elimination CH 3 CH 3 CH 3 CH 3 O CH 3 CH 3 H 3 C H D D H CH 3 H 3 C b. Aromatic Stabilization HN N H c. Faster Rate of Reaction with Br 2 /NaOH O CH 3 O C H 2 Br d. Faster Rate of Reaction with Br 2 /HBr O CH 3 O C H 2 Br e. Anomeric Hydroxyl in α -configuration O OH HO HO HO O OH H 3 CO H 3 CO H 3 CO OH OH
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f. Faster Rate of Reaction with CH 3 OH through an S N 1 Mechanism Br Br CH 3 CH 3 g. Greater Dipole Moment O O CH 3 O O H 3 C h. Faster Rate of Reaction with HNO 3 /H 2 SO 4 Br O O CH 3 i. Faster Rate of Reaction with NaOCH 3 /HOCH 3 F F MeO 2 C MeO 2 C NO 2 NO 2 j. Greater Acidity OH HO
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k. Faster Rate of Reaction in Diels-Alder Cycloaddition with cyclohexenone CH 3 OMe j. Greater Concentration of Hydrated Form at Equilibrium in water O CH 3 O H h. Greater Basicity of the Carbonyl Oxygen O N H 3 C CH 3 H 3 C CH 3 CH 3 O O H 3 C CH 3 H 3 C CH 3 i. Greater Number of Signals in the 13 C NMR CH 3 CH 3 CH 3 CH 3 j. Faster Rate of Reaction with CH 3 NH 2 through an Addition-Elimination Mechanism O O O O O
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2. (12 points) At low temperature the following Diels-Alder reaction provides mainly the endo product, while at high temperature the exo product predominates.
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This note was uploaded on 03/31/2009 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas at Austin.

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practice final exam - Chem. 310N, Spring 2008, Professor...

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