Basic Principles of Medicinal Chemistry Lab PHR 143P SUMMARY EXAM #1 October 3, 2001 | [0 ARROW PUSHING AND REVIEW LABS, wane Ly honed fol Z season 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, Examine the aqueous equilibrium below. (A) points) Are there one or more reasonable resonance Structures for the conjugate base that appears in the box? If so, draw them in the space below. (B) (S points) Based upon your answer to part A above, predict the approximate pKa associated with the above equilibrium. HINT: would you predict the pKa is most similar to an alcohol (pKa ~15), a phenol (pKa ~ 10), or a carboxylic acid (pKa ~5). Explain how you made your prediction, The ple is eppormeted eat We ressnteu i2. (2 points) Draw the Lewis dot structure for formic acid (HCO,H). 3. @ points) Draw the Lewis dot structure and any reasonable resonance forms for methylazide (CH,N,). 4. (3 points) Draw the Lewis dot structure and any reasonable for dimethylsulfoxide (CH,SOCH,). 5. (2 points) Circle the atoms that bear a partial positive charge in the following ‘compound: 3 ~ : @6. @ points) Circle the atoms that bear a negative charge or a partial negative charge in the following compound: - 7. (8 points) Show the electron flow (push arrows) for the following reaction: Show the movement of electrons by curved arrow notation for the following transformation: bp C ‘ MN Hf CH TI 8. (10 points) Show the electron flow (push arrows) for the following reaction: r —— a = . wet A wo) et eee eg ye gel hon la? ‘ wr" y we my a . + (0 ae ao