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Exam_Three_2 - WEDNESDAY 11:30 1:20 PM NAME LAST NAME GIVEN...

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1 W EDNESDAY , J ULY 23, 2008 N AME ___________________________________ 11:30 - 1:20 PM L AST N AME G IVEN N AME ID N UMBER ______________________________ SC CHEM 2020 6.0 Organic Chemistry Third Examination, Professor Michael G. Organ The exam consists of 7 questions on 11 pages. Please make sure that your copy is complete before you begin. The points for each question are given at the beginning of the question in parentheses. Only the answers written in the space indicated will be considered for marks. If you write beyond the space allocated, you will be deducted at least 1 to 2 marks from the total for your answer. An extra piece of paper has been included for you to use to rough out your answers. Questions requesting explanations MUST be done in full proper sentence form. Answers filled out in pencil will NOT be considered for re-grading. DO NOT pull exam pages apart; if pages go missing you will receive zero for those missing pages. Dy Tb Lu Yb Tm Er Ho Gd Eu Sm Pm Nd Pr Ce Rn At Po Bi Pb Tl Hg Au Pt Ir Os Uns Re Unh W Unp Ta Unq Hf Ac La Ra Ba Fr Cs Xe I Te Sb Sn In Cd Ag Pd Rh Ru Tc Mo Nb Zr Y Sr Rb Kr Br Se As Ge Ga Zn Cu Ni Co Fe Mn Cr V Ti Sc Ca K 32.06 24.305 Ar Cl S P Si Al Mg Na 18 17 16 15 14 13 12 11 12.011 10.81 Ne F O N C B He 10 9 8 7 6 5 4 3 2 H 1 Li 6.941 Be 1 H 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 IIIA IVA VA VIA VIIA 0 IA IIA IIIB IVB VB VIB VIIB VIII IB IIB PERIODIC TABLE OF THE ELEMENTS Note: Atomic masses shown here are 1977 IUPAC values. 87 88 89 104 105 106 107 109 127.60 58 59 60 61 62 63 64 65 66 67 68 69 70 71 Lr No Md Fm Es Cf Bk Cm Am Pu Np U Pa Th (244) (243) 90 91 92 93 94 95 96 97 98 99 100 101 102 103 Actinide Series * Lanthanide Series * 1.008 9.012 22.99 (223) 226.03 (261) (262) (263) 227.03 26.98 28.086 14.01 30.97 137.33 178.49 183.85 190.2 192.22 195.09 200.6 204.37 207.2 (209) (210) (222) 132.91 138.9 180.95 186.2 196.97 208.98 40.08 47.90 51.996 58.70 63.546 65.38 69.72 72.59 78.96 83.80 39.10 44.96 50.942 54.938 55.85 58.93 74.92 79.90 35.45 39.95 16.00 19.00 20.18 1.008 4.003 232.04 140.12 144.24 (145) 150.4 151.96 157.25 162.50 167.26 173.04 175.0 168.93 164.93 158.9 140.9 231.04 238.03 237.05 (247) (252) (257) (251) (258) (259) (260) (247) 87.62 91.22 95.94 (98) 101.07 106.4 112.41 114.82 118.69 121.75 131.30 85.47 92.9 102.9 107.9 126.90 88.91 Q Points Maximum 1 12 2 9 3 24 4 20 5 10 6 10 7 15 Total 100
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2 1. (a) (8 points) Are the following compounds, in whole or in part, aromatic, anti-aromatic, or non-aromatic. Place your answer on the space provided below the structure. 1 N 2 N H H 3 P 4 (+) Cl (-) P Sn (-) Na(+) H (b) (4 points) Consider reactions (1) and (2) below where sodium hydride (base) is being used to deprotonate acids 5 and 7 : (-) NaH Na (+) + H 2 NaH (-) Na (+) + H 2 (1) (2) 5 7 6 8 N H N N N H i. Which reaction (i.e., 1 or 2) occurs more spontaneously?
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