Ox \ Thoth Basic Principles of Medicinal Chemistry Lab PHR 143P oe SUMMARY EXAM #2 November 30, 2001 120 Total Points aa . af name Pay Lebsex A feels, BT vastassn > _ Fill in your answers to the questions below ON THIS SHEET. Keep your answers brief. ONLY ANSWERS WITHIN THE BOXED AREAS WILL BE GRADED. 1. @ points) Arrange the following classes of compounds in order of decreasing Rr values in a TLC experiment using silica gel as the stationary phase and 1% methanol (CH3OH) in chloroform (CHCI;) as the mobile phase. > TR Saturated hydrocarbons Polen Acids Ethers piel Hydvoterhont P Ether F Acicts @ 2. (points) Arrange the following compounds in order of increasing retention time ona reverse phase (C18 stationary phase) HPLC experiment with a mobile phase of 77% Methanol/23% Water. Ky XD dere xO AN = Acetophenone Uracil Urol, Anisole, Agpispheowna, foliant aa ee oR nee to Lor (asset 0.65 (fo te Ale tome chunfincle. csom3. (4 points) A certain barbiturate is 50% ionized in a 51:49 mixture of methanol/phosphate buffer (pH 7.2). What is the pKa of this barbiturate? (4 points) The intrinsic partition coefficient (Log P.) for Butabarbital is 1.63 and its pKa is 7.9. What is the apparent partition coefficient (Log Papp) for Butabarbital at pH 748 fog Ka = hGS eho fe = (ue?) (0.2403) ps fd. 732 5. (4 points) Phenobarbital has a pKa of 7.41 and Secobarbital has a pKa of 8.00. Which is more extensively ionized at normal physiological pH? phe pt Ht ps tal far ie Petar hats pile fy el huts beste.6 — (4points) Which amino acid is this? 7. (4 points) Which amino acid is this? g [ate wie. a aue