Midterm 2009 - Chemistry 2213a Midterm Test, Fall 2009 Page...

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Chemistry 2213a Midterm Test, Fall 2009 Page 1 1. The biggest news story of the year is undoubtedly on influenza H1N1. The gold standard for the prophylaxis and treatment of influenza H1N1 is oseltamivir (Tamiflu), shown below. Which functional group is not present in oseltamivir ? A) Ether B) Amine C) Amide D) Ester E) Ketone 2. Refer again to the structure of oseltamivir shown above. How many sp 2 -hybridized carbon atoms are present in oseltamivir ? A) Four B) Six C) Five D) Three E) Two 3. Refer to the structure of oseltamivir shown below. Which of the indicated bonds can undergo free, unrestricted 360° rotation about the bond? A) II and IV only B) I and III only C) IV and V only D) V only E) II , III , IV , and V only O N H O NH 2 O O oseltamivir O N H O 2 O O I II III IV V
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Chemistry 2213a Midterm Test, Fall 2009 Page 2 4. Oseltamivir found in Tamiflu is actually its phosphate salt, oseltamivir phosphate. As a salt, it is more soluble in polar solvents than in nonpolar sovlents. How many of the compounds below are polar molecules? CH 3 CH 2 CH 3 CH 3 CH 2 OCH 2 CH 3 CH 3 OH CF 4 CHCl 3 A) Two B) Five C) Three D) Four E) One 5. Which one of the following ions is the most stable? A) B) O F C) D) N F E) O NO 2 6. O seltamivir phosphate is made by combining oseltamivir with one equivalent of phosphoric acid, H 3 PO 4 . Phosphoric acid is a weak acid and protonates only one atom in oseltamivir. Which atom indicated below is protonated by H 3 PO 4 ? (i.e. Which atom in oseltamivir is the most basic atom?) A) III B) I C) II D) V E) IV O N H O NH 2 O O I II V III IV
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Chemistry 2213a Midterm Test, Fall 2009 Page 3 7. Tamiflu sold over the internet is sometimes made in clandestine laboratories. Illegal recreational substances are usually also prepared by clandestine operations. Which one of the recreational drugs below has the lowest p K a ? A) N HN H O N LSD B) OH N H N psilocin (magic mushroom) C) HO O GHB D) O O ecstasy E) O H H Δ 9 -THC (marijuana)
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Chemistry 2213a Midterm Test, Fall 2009 Page 4 8. Which one of the following equilibria lies furthest to the right? A) O O HN +H B r O O H 2 N Br B) HO OH O O O 2 O+ H 3 O + C) O O 2 O O O H 2 N D) O O O O E) O O O 2 O H
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Chemistry 2213a Midterm Test, Fall 2009 Page 5 9. The two structures shown below are best described by which one of A – E? O N H O NH 2 O O O O 2 O O A) They are enantiomers B) They are diastereomers C) They are cis-trans isomers D) They are different conformations of the same compound E) They are constitutional/structural isomers of each other 10. Refer to the structure of oseltamivir below. Which statement(s) is/are correct?
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This note was uploaded on 05/01/2011 for the course CHEMISTRY Chemistry taught by Professor Dr.felixlee during the Fall '11 term at UWO.

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Midterm 2009 - Chemistry 2213a Midterm Test, Fall 2009 Page...

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