The following examination contains 31 questions valued at 3.5 points/question. Please use a ½ sheet green Scantron for questions 1-23.
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1 Chemistry 106 Exam 1 Practice Spring 2018 The following examination contains 31 questions valued at 3.5 points/question. Please use a ½ sheet green Scantron for questions Name 1. Which of the following would have the largest therapeutic index value a. A cancer drug that caused nausea and vomiting, and bone marrow depression any time it was used Warfarin, a blood thinner that has been used as a commercial rat poison Heroin, which suppresses breathing at high doses Caffeine, the principal drug found in coffee 2. Which subatomic particle has the smallest mass? a. Proton Photon Neutron Electron e. Tinytron 3. Which of the following is correct concerning the charge (c) and mass (m) of the 3 subatomic particles? a. Proton c = +1, m = 1; neutron c = -1, m 0; electron c = 0, m = 1 Proton c = 0, m = 1; neutron c = +1, m = 1; electron c = -1, m 0 Proton c = +1, m = 1; neutron c = 0, m 0; electron c = -1, m 0 Proton c = -1, m = 1; neutron c = 0, m = 1; electron c = +1, m 0 e. Proton c = +1, m = 1; neutron c = 0, m = 1; electron c = -1, m 0 4. What holds atoms together in an ionic bond? a. pposite charges Like charges Shared electrons Shared protons e. Fear
2 5. Which of the following compounds is ionic? a. CCl4 CaCl2 NCl3 S3 e. All of the above 6. Which of the following is not an acid? a. H2C3 H2S4 HN3 HCl e. N/A; all of the above are acids 7. Which of the following is not a salt? a. Na2C3 CaS4 KN3 NaCl e. N/A; all of the above are salts 8. Which of the following molecules is the most polar? a. CH3CH2H CH3CH2Cl CH3CH2SH CH3CH2CH3 e. All have about the same polarity 9. Which of the following molecules has the lowest boiling point? a. CH3CH2H CH3CH2Cl CH3CH2SH CH3CH2CH3 e. All have about the same boiling point
3 10. Which of the following molecules is the most water soluble? a. CH3CH2H CH3CH2Cl CH3CH2SH CH3CH2CH3 e. All have about the same water solubility 11. Which of the following intermolecular forces accounts for the fact sodium chloride is a solid under normal conditions? a. London or van der Waal s Forces Dipole interactions Hydrogen bonding Ion-dipole interactions e. Ion-ion interactions 12. Which of the following compounds would have the greatest water solubility? a. NH 2 H e. All have about the same water solubility
4 13. Which of the following compounds would have the greatest water solubility? a. NH + Cl - 3 H e. All have about the same water solubility 14. Which of the following compounds has the greatest water solubility? a. CH 3H H H H H H H e. All have the same water solubility
5 15. Which of the following compounds is a carboxylic acid? a. H e. 16. Which of the following compounds is an alcohol? a. H e.
6 17. Which 2 organic functional groups allow drugs that possess them to be ionized depending on the ph environment they are in? a. Amine and amide Amine and alcohol Alcohol and amide Amide and carboxylic acid e. Amine and carboxylic acid 18. What is the definition of an acid? a. A proton (H + ) donor A proton (H + ) acceptor Any compound possessing an H Any compound possessing an H e. (a) & (c) 19. Which of the following is true concerning a solution of ph = 1 compared to a solution of ph = 7? a. The ph = 1 solution is 1,000,000 times more acidic The ph = 1 solution is 1,000,000 times more basic The ph = 1 solution is 60 times more acidic The ph = 1 solution is 60 times more basic e. The ph = 1 solution is 6 times more acidic 20. Which of the following is true when a buffer containing 1 M acetic acid (CH3C2H, pka = 4.8) and 1 M sodium acetate (CH3C2Na) is compares to a buffer containing 0.01 M acetic acid and 0.01 M sodium acetate? (Note: you really don t have to solve the Henderson-Hasselbalch equation shown, it is just there for you to inspect) [A - ph pka ]/[AH] = 10 a. The ph of the solution will be the same in each case The ph of the 1 M solution will be lower The ph of the 1 M solution will be higher The ph of the 0.01 M solution will be lower e. The ph of the 0.01 solution will be higher
7 21. Immediately above is the bond-line formula for the stripped down opioid meperidine (Demerol ). At what ph do you expect meperidine to be most ionized? a. ph = 2 ph = 4 ph = 6 ph = 8 e. ph = How many covalent bonds does chlorine form when neutral? a e How many covalent bonds does chlorine form when it bears a -1 charge? a e. 4
8 24. Please draw the Lewis structure for the acutely toxic, highly carcinogenic, former dry cleaning agent carbon tetrachloride, CCl4, including non-bonded pairs of electrons 25. Please draw a legitimate Lewis structure for the organic solvent pentane, C5H12. Every additional isomer drawn will earn 1.75 extra credit points 26. Please draw a legitimate Lewis structure for the common drug formulation additive glycerol, C3H83, including non-bonding pairs of electrons. Every additional isomer drawn will earn 1.75 extra credit points (limit 4 additional isomers). Bonus (1.75 EC): Is glycerol soluble in water? Why or why not?
9 27. Please redraw the bond-line structure for the analgesic agent meperidine (Demerol ) as the complete Lewis structure N 28. In the acid-base reaction below, indicate the conjugate base of the acid and the conjugate acid of the base by drawing a line between them and labeling. Label both members of each pair. Mg(H)2 + 2HC2H 2H2 + Mg(HC2)2 29. Please complete the following acid-base reaction H2C3 + 2NaH 30. Please complete the following acid-base reaction H2CC2H + 2NaH 31. Please complete the following acid-base reaction between amphetamine and sulfuric acid to generate the principal component of Adderall. Feel free to use R to represent the portion of the amphetamine molecule not participating in the reaction (R as in remainder, or like what-ever) so you don t have to redraw the whole structure 2 + H2S4
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