Download Chemistry Exam II - October 2, 2007 - Prof. Thomas J. Barton and more Exams Organic Chemistry in PDF only on Docsity! 1 Last Name___________________ Seat No. _______________ First Name________________________ (Please print your name) Circle your recitation number and time: (1) Fri. 12:10 PM, (2) Fri. 2:10 PM, (3) Fri. 3:10 PM, (4) Mon. 12:10 PM, (5) Mon. 1:10 PM (6) Mon. 4:10 PM (7) Tues. 9:00 AM (8) Tues. 12:10 PM (9) Tues. 1:10 PM (10) Fri. 9:00 AM (11) Fri. 11:00 AM (12) Mon. 11:00 AM (13) Mon. 2:10 PM (14) Tues. 10:00 AM There are 6 pages to this exam. Check to make sure you have a complete exam. CHEMISTRY 331 EXAM II Tuesday, October 2, 2007 I. (30 points) II. (26 points) III. (18 points) IV. (14 points) V. (12 points) TOTAL (100 points) Ia. Give the proper name for each including sterochemical designation when required. (18 pts) H H b. Write the structure for each of the following. (12pts) 3-methyl-1-pentene 3,4-dibromo-1-butene (Z)-3-methyl-2-octene cis-1,4-divinylcyclohexane 8A 18 7A 17 6A 16 5A 15 4A 14 3A 13 109 Une (266) 108 Uno (265) 107 Uns (262) 106 Unh (263) 105 Ha (262) 104 Rf (261) 89 Ac 227 88 Ra 226 87 Fr (223) 83 Bi 209 82 Pb 207 81 Tl 204 80 Hg 201 79 Au 197 78 Pt 195 77 Ir 192 76 Os 190 75 Re 186 74 W 184 73 Ta 181 72 Hf 178 57 La 139 56 Ba 137 55 Cs 133 51 Sb 122 50 Sn 119 49 In 115 48 Cd 112 47 Ag 108 46 Pd 106 45 Rh 103 44 Ru 101 43 Tc (98) 42 Mo 95.9 41 Nb 92.9 40 Zr 91.2 39 Y 88.9 38 Sr 87.6 37 Rb 85.5 86 Rn (222) 85 At (210) 84 Po (209) 52 Te 128 53 I 127 54 Xe 131 36 Kr 83.8 35 Br 79.9 34 Se 79.0 33 As 74.9 32 Ge 72.6 31 Ga 69.7 30 Zn 65.4 29 Cu 63.5 28 Ni 58.7 27 Co 58.9 26 Fe 55.8 25 Mn 54.9 24 Cr 52.0 23 V 50.9 22 Ti 47.9 21 Sc 45.0 20 Ca 40.1 19 K 39.1 18 Ar 39.9 17 Cl 35.4 16 S 32.1 15 P 31.0 14 Si 28.1 13 Al 27.0 2 He 4.00 10 Ne 20.2 9 F 19.0 8 O 16.0 7 N 14.0 6 C 12.0 5 B 10.8 8B 2B 12 1B 111098 7B 7 6B 6 5B 5 4B 4 3B 3 12 Mg 24.3 11 Na 23.0 4 Be 9.01 3 Li 6.94 2A 2 1A 1 1 H 1.01 2 IVa. Circle the alkene which should give two constitutionally isomeric products when allowed to react with HBr? (3pts) b. The addition of HCl to 1-isopropylcyclohexene yields a rearranged product. Propose a mechanism, showing the structures of the intermediates and using curved arrows to indicate electron flow in each step. (8pts) ClHCl c. Circle the appropriate reaction energy diagram for the above reaction. (3pts). Reaction Progress E ne rg y Reaction Progress E ne rg y E ne rg y Reaction Progress 5 V. Write the product(s) for any 4 of the following 8 reactions. Mark an X in the box of any omitted questions. Show the stereochemistry where required. If you answer all questions only the first 4 will be graded. (12 pts) Br2 H+, H2O HBr CH3 1) BH3, THF 2) H2O2, -OH 1) Hg(OAc)2, H2O,THF 2) NaBH4 Br2/ H2O HCl OH H2SO4, H2O heat 6
