8 Basic Principles of Medicinal Chemistry Lab PHR 143P SUMMARY EXAM #1 October 2, 2002 ARROW PUSHING AND HPLC LABS NAME Gregory Mester _ 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. (3 points) Draw the Lewis dot structure and any reasonable resonance forms for methylazide (CHN,).+16 points) Show the electron flow (push arrows) for the following reaction: Ca ao, Hao W Scr, qe <2 he hy 4. (8 points) Show the electron flow (push arrows) for the following reaction: 0. Y Nu: S. ° * | Feb“ mT + A ee nH 5. © points) Identify on the structure bel would could as ELECTOPHILIC sites low ALL of the CARBON ATOMS that of attack by a nucleophile. SS partial pisthve charge, é oO Gy, CHa ha ri ts al eS zy RB E {| Gy = a 16-8. (12 points) For each of the three chemical steps shown below , sw the flow of electrons by “pushing arrows”. ‘Base HlBase* “Base 7 Me, \ — Zs) eet Nso J ie Son Se. wor, 9. (5 points) Arrange the-Yollowing three compounds in order of decreasing R, values in a TLC experiment using silica gel as the stationary phase and 1% methanol (CH,OH) in chloroform (CHCI,) as the mobile phase. ‘pan’ HN-CR ven olor nonpslar i OGG > te > ego TRe a .