Exam 1 F'08

Exam 1 F'08 - CHEM 312—Van Draanen Midterm Exam October...

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Unformatted text preview: CHEM 312—Van Draanen Midterm Exam October 22, 2008 NAME Questions Points 1-10 /30 11-15 /30 16 /30 17-21 /30 22 /8 23 /7 24 /5 25 /10 TOTAL /150 Questions 1-10: Multiple Choice. 3 points each, 30 points total. Select your answer(s) from the given choices: 1. Which of the following are isomers of C8H10O (circle all that apply) O OH O O O O 2. How many units of unsaturation are there in pyridine? N a. 3 b. 3.5 c. 4 d. 5 3. Circle which of the following you would expect to be the MOST water soluble? OH NH OH OH OH 4. Circle which of the following you would expect to have the highest boiling point? OH NH OH OH OH 5. Which of the following is an anionic detergent? O SO O N OH O O 6. Which of the following would you expect to be colored (circle all that apply) O O OH O OH OH HO Questions 7-10 refer to the molecule below: O 8 6 9 7 4 5 2 3 1 7. What is the geometry of carbon #2? a. trigonal planar b. bent c. tetrahedral d. linear 8. What is the bond angle around carbon #7? a. 109.5˚ b. 120˚ c. 180˚ d. can’t tell 9. What is the functional group at carbon#4? a. ketone b. aldehyde c. ether d. alcohol 10. Could this compound be used as an oxygenate in gasoline? YES NO Questions 11-15. Nomenclature. 6 points each, 30 total. Provide the IUPAC name or the structure for the following: Cl 11. O NH2 12. OH 13. p-chlorotoluene 14. 4-chloro-N-ethyl-N-methylhex-4-en-3-amine 15. 4-hydroxy-3,3-dimethyloctanal 16. Reactions. 30 points total. Give the major organic product from each of the following reactions. polymerization H+/H2O Cl2 1. BH3 2. NaOH/H2O2 epoxidation 1 . H+ 2. H+/H2O 1. BH3 2. NaOH/H2O2 (6 points) In the lab, how would you make a gasoline with an octane number of 68.5? How well would it work in a car? 17. (3 points) If a compound absorbs orange light, what color will the compound be? 18. (6 points) Which is absorbing light of a higher wavelength: a purple compound or a green compound? Explain your answer. 19. (7 points) The dehydrogenation of ethylbenzene to form styrene is an endothermic reaction. How can the reaction be run successfully? Pd + H --H 20. (8 points) Which of the following carbocations is more stable? Explain your answer using words and pictures. O Cl 21. Energy diagram. 8 points. Fill in the energy diagram based on the mechanism drawn below and the following information: H O Cl - O + Reactants Cl OH H Cl A a. this reaction is spontaneous b. the first step of the reaction is the slow step Label your energy diagram, being sure to include the following parts: a. axes b. reactants, products, intermediate(s) c. Ea, ∆ Erxn Product 22. Enthalpy calculation. 7 points. For the reaction in Question 23, calculate the DH˚ for the reaction. Some of the following bond dissociation energies should be helpful: C—O, 347; H—H, 435; O—H, 435; H—Cl, 431; C—Cl, 335 kJ/mol. Show your work and box your answer clearly. H O Cl - O + Reactants Cl OH H Cl A Product 23. The first “Explain.” 5 points. The reaction above (the opening of the epoxide) works very well and is definitely spontaneous. Explain, using your answer to Question 24 in your explanation. 24. The big “Explain” question. 10 points. In the reaction of ammonia with ethylene oxide, shown below, it’s hard to stop the reaction at the formation of ethanolamine. OH O + NH3 HO NH2 ethanolamine O HO H N O OH diethanolamine N HO OH triethanolamine O OH HO quaternary ammonium salt N OH O- It’s even hard to stop it at the formation of diethanolamine. The reaction will spontaneously continue until triethanolamine is formed, regardless of the stoichiometry of the starting reagents. That is, even if one mole of ammonia is reacted with one mole of ethylene oxide, a significant amount of triethanolamine will be isolated. Explain this result. Include in your explanation some discussion of the reactivity of the nitrogen and the relative rates of the various steps. Also explain why the reaction stops at triethanolamine and doesn’t continue until the quaternary ammonium salt is formed. 2 18 VIIIA 10 He4.0 1 36 9 F 35 17 34 16 7 33 15 6 52 51 69 14 32 50 Er B 31 81 13 49 10.8 Al27.0 Ga69.7 In 114.8 Tl 204.4 30 12 IIB 48 80 Zn65.4 Cd 112.4 29 11 IB 47 28 9 27 7 VIIB PERIODIC CHART OF THE ELEMENTS 26 106.4 77 44 76 25 43 75 23 22 42 74 107 106 73 40 72 105 Cm (247) 95 Eu152.0 Am (243) 94 Pu(242) Sm 150.4 195.0 ¤ Cr52.0 Mo 95.9 W 183.9 (263) 41 96 Gd 157.3 62 108 Bk (247) 158.9 61 93 Pm (147) 60 Np (237) 92 U Nd 144.2 59 Pa 140.9 (231) 90 58 Th Ce140.1 57 238.0 91 Pr Mn 54.9 Tc (99) Re 186.2 Ns 24 97 63 109 Cf(249) Tb 64 Pt Es(254) 98 65 Fe 55.8 Ru Os 190.2 Hs 101.0 VIB 5 VB 45 78 99 162.5 Co58.9 Rh102.9 Ir 192.2 Mt VIII 8 46 Ni 58.7 Pd Fm (253) Dy Cu63.5 Ag107.9 Au197.0 10 100 Ho164.9 Hg200.6 79 Md (256) 167.3 12.0 Si 28.1 Ge72.6 Sn 118.7 Pb 207.2 5 101 66 82 No (253) Tm 168.9 67 83 102 173.0 68 84 C 13 IIIA 232.0 89 Lanthanides Actinides(227) V 50.9 Nb La138.9 Ac (262) 92.9 Ta 180.9 Ha * ** 104 Ti 47.9 Zr 91.2 Hf 178.5 Rf(261) IVB 21 4 2 IIA 12 3 H 1.0 71 103 11 Li 6.9 20 38 56 88 Mg 24.3 Ca40.1 Sr 87.6 Ba137.3 Ra (226) Be9.0 1 39 Sc 45.0 Y 88.9 Lu 175.0 Lr(257) ** * IIIB 1 IA 85 Yb N 14.0 P 31.0 As 74.9 Sb Bi 209.0 121.8 14 IVA 3 53 70 Rn (222) O 16.0 S 32.1 Se 79.0 Te 127.6 Po(210) 15 VA 4 86 I At(210) 19.0 Cl 35.5 Br 79.9 126.9 8 16 VIA 6 54 131.3 H 1.0 17 VIIA 18 Ne20.2 Ar39.9 Kr83.8 Xe 19 37 55 87 K 39.1 Rb85.5 Cs Fr Na 23.0 132.9 (223) Revised 1993 ...
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This note was uploaded on 10/24/2011 for the course CHEM 312 taught by Professor Bailey during the Spring '03 term at Cal Poly.

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