chm138h-m08 - mun-fins rm Name Student Number Demo Group...

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Unformatted text preview: mun-fins; -- rm . . Name: Student Number: Demo Group: UNIVERSITY OF TORONTO FACULTY OF ARTS AND SCIENCE APRIL/MAY EXAMINATIONS 2008 CHM 138H1 S Duration: 3 Hours Aids allowed: molecular models and a non-programmed calculator. A periodic table is attached to the back of the exam. The examination consists of two parts, A and B. Part A consists of 15 multiple choice questions, worth 2 marks each (total = 30 marks), which are found on pages 3-6. These questions must be answered on the computer sheet that accompanies this . , exam. * ' ' Part B consists of 5 short answer questions; worth atotal of 70 marks, found on pages 6-8. These questions must be anSwered on the answer sheets thatare attached to the back of the exam. PART A: Multiple Choice Questions. 1. THERE ARE 15 QUESTIONS ON PAGES 3- 6. CHECK THAT YOU HAVE THE RIGHT NUMBER OF QUESTIONS AND PAGES.‘ 2. Write your last name and initials 'in the appropriate areas of the computer form and fill in the corresponding 'bubbles' beneath them. (Hyphenated last names should be bubbled in without spaces or dashes.) Similarly, provide your student number in the box on the left of the computer form. 3. In the Subject box, write CHM 138 and your demonstrator group number. 4. Sign your name in the Signaturevbox. 5. Do not to make *ANY". marks outside of the shaded area.» If any stray marks are made, the test form will not be graded. YOUR ANSWERS ARE TO BE RECORDED ON THE COMPUTER ANSWER SHEET AND ON THIS PAPER, BOTH OF WHICH MUST BE HANDED IN AT THE END OF THE TEST. NOTHING ELSE WRITTEN ON THE TEST PAPER WILL BE MARKED. - DURING THE TEST: 1. Clearly circle on the test paper the'letter (a, b, c, d or e) for the be_st ansWer you choose for each question. 2. On the computer sheet, blacken the circle (below a, b, c, d ore) which corresponds to the answer you have chosen for each question. Make sure that only one answer is blackened. Make heavy black marks that fill the circle completely 3. Use soft pencil only (No.2 or softer). Do not use ink or ball point pen. 4. Erase cleanly any answer you wish to change. 5. Make no stray marks on the answer sheet. 6. The computer sheet MUST be filled in DURING the time allotted} for the test. AT THE END OF THE TEST: Insert your computer answer sheet into your test paper. Remain seated until all test papers have been collected. / / 20f8 1. Which of the following compounds is least likely to react by either an SNl or 8N2 mechanism? _ (a) ' 1 (b) (C) ’ - (d) . (C) l >‘\ 0 All of (a)-(d) can react /\/CI GA Br —lj . O‘é—Q— well by both I , _ > Br ‘ 0 , mechanisms. COZH D (a) Carbon atom A (b) Carbon atom B (0) Carbon atom ‘c (d) Carbon atom D (6) Carbon atom E . ‘ 3.. Rank the carbocations below in order of decreasing stability: 4 @- G) M *Q N M -_ V 11-," III I . _IV (a) III>I>II>IV (b) II>IV>III>I ' (c)II>III>I>IV (d)II>I>III>IV (e)IV>II>'III>I ' » 4. Which of the following compounds cannot give a stable Grignard. reagent? to) ' _ (d) (e) . Br All of(a)-(d) giv (a) (b) . ’ Br I B a ' l - stable Grignard * . ' r Br . . reagents. /|\/ so/\/ I H O‘ . l 3of8 ’ 5. What is the maj or-product in the'reaction) of 2-bromo-3-methylbutane with KO‘Bu in ethanol? a) ; (b) . , ' (e) \I : \ O‘Bu (C)\I_— \/ \I :002H5 6. . Determine which of the following compounds is npjlaromatic: (b) , (c) (d) ' . (e) V6 G 1 I . VG C 7. An unknown Organic compound reacts under ozonolysis conditions to give only one product. The same compound also consumes 2 equivalents of H2 1n the presence of Pd catalyst. Which of the following compounds 18 the unknown compound? be“? mm 8. Which reaction conditions would give the following transformation? (a) KMO4, 1130* (b') 1. 03; 2. Zn/CH3CO2H . (c) 1. Hg(OAc)2/H2Q; 2. NaBH4 '(d) 1. BH3/THF; 2. 011711202 - (e) None ofthese. 4of8 9. Find the combination of conditions that are the _b___est for an SNZ reaction: /\ (a) The substrate is a primary alkyliodide, solvent is aprotic and polar, and the nucleophile is a strong base. (b) The substrate is a primary alkylfluoride, solvent is protic, polar and the nucleophile is a strong base. (c) The substrate 1s a primary alkyliodide, solvent 1s non-polar and the nucleophile 1s a weak base. (d) The substrate is a tertiary alkylfluoride, solvent 15 non-polar and the nucleophile IS a strong base. (e) The substrate 18 a tertiary alkyliodide, the solvent 18 aprotic and polar, and the nucleophile 1s a . strong base. 10. Which of the following substituted cyclohexanes'will 1g); undergo E2 reaction? (a) (b) ’ (C) (d) - (C) H H _ ' H H They all can WW“ Cl _ ‘C. H C! undergo E2 Magi. % reaction ' H H H H C, H ' H CH20H3 Questions 11-15 pertain to the structure of amoxicillin (C16H19N3058), a synthetic antibiotic similar to penicillin: COOH A""> NH2 11. What can be said about the hybridization of N atoms marked A and B in the structure above? (a) atom A Is sp3 Zhybridized and atom B Is Sp :hybridized (b) they both are sp3 hybridized (c) atom A Is Sp) hybridized and atom B IS sp3 hybridized ((1) they both are spz hybridized . (e) none of the above » . 12. How many chirality centres does amoxicillin have? @2 (wi' cm.' @5, (e6 13. How many prochiral Sp3 hybridized carbon atoms does amoxicillin have? @0' (m1 en @3 (e4 50f8 14. What is the degree of unsaturation of amoxicillin? (a) 5 ' (b) 7 ‘ (c) 9 (d) 11 (e) 13 l ’15. Which of the following absorptions would you expect to see in an IR spectrum of amoxicillin? (a) ~ 3500 and ~1710 cm" I (b) ~3500 and no ~1710 cm" (c) ~1710 and no ~3500 cm" ; (d) neither ~3500 nor ~1710 cm" PART B: Short Answer Questions . l (8 marks). (a) On the templates provided on the answer sheet, draw the two' major products of the reaction of cis-l-phenyl-l-butene with Brz. ' (b). Mark the absolute configuration (R or S) of any chirality centres in your products. , 2 (16 marks). On the answer sheet, draw the struCtures of the reactant, reagents and/or the majbr product (A — F as well as Nu- and Y") of reactions (a) —— (c). Where necessary, be sure to include appropriate regiochemistry and/or stereochemistry. 1 BH /THF 2 B " 4 \q 44—» A —)" c (an alcohol) Ph H H2804 . . -————>_ D H CzH5 I H20 H , (C) - ,E+:Nu' —“'—> Nu' = nucleophile, Y' 5 leaving group . 6of8 3 (20 marks). (a) Draw a complete mechanism that accounts for the formation of the product shown below. Use appropriate arrows to indicate the direction of electron flow and show the structure of all intermediates (the structures of transition states are NOT required.) OH H30-+ __.—_.______) HzO/THF (b) What would be the best region of the IR spectrum to use in order to monitor the progress of this reaction? ‘ . ‘ (c) Is the acid H30+ needed in a catalytic amount or stoichiometric amount inorder to carry out this transformation? ((1) Is this reaction stereospecific? From your reaction mechanism, provide a brief explanation for your answer. ' > 4 (11 marks). Consider the following reaction: . > . ' 0 Br ' ' CH3COONa ' —-—--———-——> CH3COOH/HZQ (a) Using the axes provided on the answer sheet, draw the free energy diagram for this reaction. (b) On your diagram, writevthe letter "R" to show the location of reactants. (c) On your diagram, write the letter "P" to show the location of products. (d) Write the letter "I" to show the location of all intermediates and the letters "TS" to show the location of all transition states. (e) Write "AGI" to indicate the activation energy barrier for the reaction’slrate determining step. (f) Write "AG". to indicate the overall energy change for the reaction. 7of8 5 (1 5 marks). In the boxes provided on the answer sheet, draw the structures of the organic reactants and/or products A -— F and, reagent G for the transformations below. ' C . H2/Pd sto4/Hzo' ' G A -——-————————-—>B—————————> D+E SOC12 NaOCH3, CH3OH 1) product D Cl Mg/ether 2) H30+ ——"‘_'>F——-——-—-—>’HO — END OF THE EXAM — 8of8 , Periodic T ableof Elements .18 2 4.002602 He 16' ©1998-2000 Reid-it Limited =mwwu5 2§2§.-§'2§§5§§ . , 8 14 6 12011 C Carbon 13 2698214 28006 SI Siioon . 32 72.61 Ge Gennanimn 50 118.7151 Sn Tin (Shnmm) 207 Pb Lead [285] mm 074.11qu 3 .3. 5 ,~s g 5 2295 2§88§=s§§=§ n E 2 S a: 1515‘ if Cd Cadmum no 20059 H9 WWW) [ 12 {2 uu mm ummium Ununblum s r- § 3 a 5: ‘:§ Etc); 8‘: N :3 ° <§gv<§§§ 3"; 2 e a S8m§ .812 55.35% 73 En: ESDE o9012377l19222 u .845 01.07 6Transition Elements 7998 W“ 8475 R18621 76 147 B[262.12]1OB E S? "tong "510% E 3 I 42M 5.94 Tuwm i -1106 $126312} $656019 Eff 6.6; “ >§ 25 PE 3 . a T 3.- E SE #- ghgmfi:35§ .—. go? . E-- §E~§ E 939% EET ng :083’4: e 214495622 5:10 88.906 57138.91 2 La“La 203 Adll‘llllm ”392078 3173 .33 S87 .62 4 :38 56mm“ 13.291 TOY 17.1 Noble Gases w [262.11] Lr Halogens T6833 me 68 E167.“ Ho l-lolmimn 99 [252.08] 00 [257.1 Es .u y [2511; off 66 162.50 57 164.93 I ‘-“-' m I 65 T‘lb58.93 157. 25 A7413“ 7.051 END mp"? um 61 (144.911 so 14424 Nd 59 P140. 91 91 P231.0492 Lanthanides (Rare Earths) 58 140.12 90 23204 A . (mass: longest lived Isotope] Kw Element Symbol Alkaline Earths Alkali Metals atomic no 62 150.36 63 151.-96 Eillil Sama'ium 94 [244.06] 95 Pu Plutonilm ) MM (name: historical or alternative name) CHM 138HIS Final Examination Answer Sheet Student #: 1 (8 marks). Two major products of the reaction of cis-l -phenyl-1-butene with Brz. Mark the absolute configuration (R or S) of any chirality centres in your products. PLEASE HAND IN 2 (16 marks). Draw the structures of A - F as well as Nu‘ and Y'. A C F Question Mark CHM 138HIS Final Examination Answer Sheet Student #: 3 (20 marks . (a) Complete mechanism that accounts for the formation of the product: (b) The best region of IR spectrum to monitor the progress of this reaction: (c) Is the acid H3O+ needed in a catalytic amount or stoichiometric amount? ((1) Is the reaction stereospecific? Explanation: CHM 138HIS Final Examination Answer Sheet Student #: Demo Gp.: 4 (11 marks). (a)-(f) Free energy Reaction coordinate 5 (15 marks). Structures of organic reactants and products A — F and reagent G. ...
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