Basic Principles of Medicinal Chemistry PHR 143M EXAM #1 OCTOBER 1, 2003 LECTURE Q NAME osu | Fill in the ScanTron sheet with the SINGLE BEST ANSWER to the following questions. ONLY the ScanTron sheet will be graded; you will receive no credit for answers marked on this question sheet. 1. Below is a table listing the boiling points of a series of halogenated hydrocarbons. ‘What forces are responsible for the trend observed in this table? P=0.84 logenate: carbon ‘ofnt fethyIchloride (Ci romomet 1) lodomethane Increasing van der Waals intermolecular attraction between molecules with an increase in molecular size (e.g., number of electrons) Decreasing van der Waals intermolecular attraction between molecules with an increase in molecular size (e.g., number of electrons). Increasing Inductive stabilization of the intermolecular attraction between molecules with a decrease in the number/magatude of bond dipoles. Decreasing Inductive stabilization of the intermolecular attraction between ‘molecules with an increase in the number/magnitude of bond dipoles. None of the above are correct. =5 9 3@ Partition co-efficients are expressed as logP values. These logP values relate to the partitioning of the drug between an aqueous phase and an organic phase, typically ‘water-saturated n-octanol. The logP value is defined as: P=0,99 @) The log of the ratio of the concentration of the drug in the organic phase over the concentration of the drug in the aqueous phase. B. The log of the negative of the ratio of the concentration of the drug in the aqueous phase over the concentration of the drug in the organic phase. ‘The negative log of the ratio of the concentration of the drug in the aqueous phase over the concentration of the drug in the organic phase. The negative log of the ratio of the water solubility of the drug over the organic phase solubility of the drug, None of the above are correct. moo3. ___ Based upon the structures of the two barbiturates below, predict their relative artition co-efficients and water solubilities “ 0; a ~O, mee NH NH 8 nn = Barbiturate A Barbiturate B Barbiturate C O88 ‘A. Barbiturate A is more water soluble and has a higher LogP than barbiturate B. Barbiturate A is less water soluble and has a higher LogP than barbiturate C. Barbiturate A is more water soluble and has a lower LogP than barbiturate C. Barbiturate B is less water soluble and has a lower LogP than barbiturate C. Barbiturate B is more water soluble and has a lower LogP than barbiturate C. 4. The two isomers of THC that we discussed in class exist due to: THC P=0.55 ® The variation in the position of the carbon-carbon double bond indicated by the dotted arrow. B. The variation in the stereochemistry of the position indicated by the solid arrow. CC. The variation in the numbering system used to name this compound. D. The variation in the electronegativity of the sp? and sp* carbons in this compound.Has to he x OF ee oO O Br 6 D: Cj E. II four molecules above are aromatic (follow Huckel's rule). 6. Which of the following lists is in increasing order of size (smallest molecule to largest molecule): P=10 ‘A. chloromethane, bromomethane, iodoform (CHL), methanol, methane . methanol, methane, bromomethane, iodoform (CHI,), chloromethane ‘methane, methanol, chloromethane, bromomethane, iodoform (CHI,) . iodoform (CHI), chloromethane, methane, methanol, bromomethane E, methanol. methane, iodoform (CH,1), bromomethane, chloromethane. 7. Which of the following molecules is most lipophilic (e.g., has the largest LogP)? P=0.78 x ON 0 . re) ke o, ~ a RE) qh CAH MoM gueat iees MULE sot pple (te Pd