14C_f09_finalB

14C_f09_finalB - Chemistry 14C Fall 2009 Final Exam Part B...

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Chemistry 14C Fall 2009 Final Exam Part B Page 1 Page 1 score = The questions on this page concern ciprofloxacin (trade name Cipro), an antibiotic that works by binding to DNA gyrase (an enzyme used in DNA replication), causing double-stranded breaks in the bacterial chromosome, and bacterial death. This drug gained worldwide recognition as the primary defense against the bioterrorist anthrax threats of 2001. N F N NH O O HO ring A ring B ring C ring D Ciprofloxacin 1. (3) Draw another very significant resonance contributor in the box. Include all lone pairs in your new resonance contributor. N F N NH O O HO 2. (2) List two very specific and very different ways in which resonance influences the structure and properties of ciprofloxacin. Influence #1 ( ten words or less ) : Influence #2 ( ten words or less ) : 3. (5) The carboxylic acid and ring B portions of ciprofloxacin are (circle one): perpendicular coplanar Finish this sentence in twenty words or less : The carboxylic acid and ring B have this geometry because... 4. (2) Circle the conjugated atoms of ciprofloxacin. One circle per atom. N F N N O O O H H 5. (2) Write a number. The total number of pi electrons that reside in ciprofloxacin’s aromatic rings is _________. 6. (2) Circle the letter(s) of the ciprofloxacin ring(s) that are planar: A B C D None of these
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Chemistry 14C Fall 2009 Final Exam Part B Page 2 Page 2 score = Questions 7–12 concern the structure of penicillin G, another commonly known antibiotic. N S CH 3 CH 3 COOH N O H O Penicillin G 7. (4) Write numbers in the blanks. Of the carbon stereocenter(s) in penicillin G, ___________ have an R configuration, ___________ have an S configuration, and ____________ are not R or S . Not including the structure shown above, there are _____________ penicillin G stereoisomers.
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