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1OHOHOHOHOHOHOHCOOHOHCOOHBASIC PHARMACEUTICAL SCIENCE FOR THE PRACTICING PHARMACIST MEDC 527, Fall 2008 Quiz #1, Dr. Desai, 100 points; September 9, 2008 (Signature) 1. Rank the molecules according to their expected mp/bp. Use 1 for least and 3 for highest mp/bp. (6 pts) 2. Circle the molecule in the pair that is expected to have higher boiling/melting point. (8 pts) a) CH3CH2F; HF b) 3. Write the Henderson – Hasselbach equation for the following equilibrium. Define the terms involved. (12 pts) PhCOOH + H2O ⇐⇒ PhCOO- + H3O+ ______________________________________________________________________________ ______________________________________________________________________________ ______________________________________________________________________________ ______________________________________________________________________________ ______________________________________________________________________________ 4. In few sentences, explain why I is expected to have lower pKa than II. (6 pts) NCOOHCH3CH3CH3COOHCH3CH3CH3+Cl_ I II ______________________________________________________________________________ ______________________________________________________________________________ ______________________________________________________________________________ ______________________________________________________________________________ IV V VI VII2 C N O F 3 Si P S Cl 4 Ge As Se Br5 I STUDENT NAME (in CAPITAL Letters ONLY)VCU ID #2ICOOHFCOOHCOOH5. Rank the molecules/ions in each series according to their pKa values. Use 1 for the least pKa value, 2 for the next higher and so on. (18 pts) a) O2N-CH2-CH2-COOH CH3-CH-COOH CH3-CH-COOH b) c) F-CH2-COOH CH3-COOH Br-CH2-COOH 6. The molecule underneath is potential diagnostic marker for an anti-estrogenic agent. Indicate the Kier-Hall electronegativity values of the following atoms. (8 pts) Kier-Hall eN Value -O- of phenolic OH =__________________________ I- =__________________________ S =__________________________ F of CF2 =__________________________ 7. In few sentences, explain why the bp of I is expected to be higher than that of II. (6 pts) COOHI II ______________________________________________________________________________ ______________________________________________________________________________ ______________________________________________________________________________ 8. Amyl nitrite is a nitrovasodilator. The structure of amyl nitrite is (CH3)2CHCH2CH2-O-N=O. Write the electronic structure of its nitrogen and the double bonded oxygen atoms and indicate their hybridization states. (8 pts) The electronic structure of N is _______________________________________________ The hybridization state of N is ________________________________________________ The electronic structure of =O is ______________________________________________ The hybridization state of =O is _______________________________________________ COOH NO2 OH(CH2)9SO(CH2)3CF2CF3OHI3 9. Indicate whether the following drugs or biological molecules will exhibit good water solubility at pH 7.2-7.4. Circle the correct answer. (16 pts) A) Soluble OR Insoluble B) Soluble OR Insoluble OCH3CH3CH3CH3COOHGemfibrozil OHCholesterol C) Soluble OR Insoluble D) Soluble OR Insoluble OCOCH3COOHAspirin COOHCH3CH3CH3Ibuprofen 10. Azidothymidine (below) is an inhibitor of HIV reverse transcriptase enzyme. Write the hybridization state of non-hydrogen atoms marked ‘a’ (oxygen), b’ (nitrogen), ‘c’ (carbon), ‘d’ (nitrogen), ‘e’ (oxygen) and ‘f’ (nitrogen). Also indicate the type of geometry corresponding to the hybridization. (12 pts) Hybridization state Type of Geometry a = _____________________ _______________________ b = _____________________ _______________________ c = _____________________ _______________________ d = _____________________ _______________________ e = _____________________ _______________________ f = ______________________ _______________________


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VCU MEDC 527 - MEDC 527 quiz 1

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