Final_3311f06_key

Final_3311f06_key - CHEM 3311-200 Fall 2006 Average Score =...

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CHEM 3311-200 Fall 2006 Final Exam Professor R. Hoenigman I pledge to uphold the CU Honor Code: Signature______________________________________________ Name (printed)____________________________________________________ Last four digits of your student ID number_______________________________ Recitation TA_____________________________________________________ Recitation number, day, and time______________________________________ You have 2 hours and 30 minutes to complete this exam. No model kits or calculators allowed. Periodic table and scratch paper are attached. DO NOT TURN THIS PAGE UNTIL INSTRUCTED TO DO SO. Recitation Sections: # Day Time TA 211 Monday 8 am Noel 251 Monday 2 pm Carolynn 291 Monday 5 pm Heather 252 Tuesday 12 pm Sam 293 Tuesday 5 pm Carolynn 212 Wednesday 8 am Noel 253 Wednesday 1 pm Tom 292 Wednesday 5 pm Heather 213 Friday 8 am Heather Score: Page 1 ____________/16 Page 6 ____________/40 Page 2 ____________/15 Page 7 ____________/40 Page 3 ____________/20 Page 8 ____________/24 Page 4 ____________/30 Page 9 ____________/45 Page 5 ____________/20 Page 10 /10 TOTAL ____________/250 Average Score = 145 High Score = 235 Low Score = 27
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CHEM 3311, Fall 2006 Final Exam, page 1 of 12 1. (10 pts) BenzaClin is a topical antibiotic with the structure shown below. A. Label the configuration of each indicated chirality center in BenzaClin. (2 pts each) B. Circle all of the terms below that describe one or more structural feature of BenzaClin. (1 pt each) Amine Ketone Aldehyde Amide Ester Sulfide Nitrile Ether Thiol O C N N O OH OH n -Pr S OPO 3 H 2 Cl H H R R R 2. (6 pts) Give the IUPAC name for each of the following compounds. (2 pts each, -1 for no stereochemistry, -1 for wrong numbers) A. (3 Z ,5 R )-3,5,6,6-tetramethyl-3-heptene B. Br OH (3 S ,4 R )-4-bromo-5-ethyl-2,5-dimethyl-3-heptanol C. F O para -fluoroacetophenone (or 4-fluoroacetophenone)
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CHEM 3311, Fall 2006 Final Exam, page 2 of 12 3. (5 pts) Vitamin C, shown below, has a p K a of 4.1. Circle the most acidic hydrogen in Vitamin C. O O HO OH C H H OH CH 2 OH 4. (10 pts) Explain why an ester can be both an activating, ortho/para director and also a deactivating, meta director. Use resonance structures to support your discussion. (4 pts for resonance structures, 6 pts for explanation)
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Final_3311f06_key - CHEM 3311-200 Fall 2006 Average Score =...

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