chm138 past tests - Name: Student Number: Demo Group: I I ,...

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Unformatted text preview: Name: Student Number: Demo Group: I I , UNIVERSITY OF TORONTO FACULTY OF ARTS AND SCIENCE DECEMBER EXAMINATIONS 2007 CHM 138H1 F Duration: 3 Hours Aids allowed: unprogrammed calculators and molecular models. ' 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 3-7; These questions must be answered on the computer sheet ' that accompanies this exam. 0!! the computer sheet! ' 1. Write in your student number and bubble it in, as well as your last name and initials. 2. In the Subject box, write CHM 138 and your demonstrator group number. 3. Sign your name in the Signature box. V . . . 4. Do not write ANYTHING outside ofthe boxed areas. Ifany stray marks are made, the test form will not be graded. - Further instructions for filling in the computer sheet are found on page 2. Part B consists of 9 short answer questions, worth atotal of 80 marks, found on pages 8-11. These questions must be answered on the answer sheets which are attached to the back of the exam. ' ' Page 1 ofll 1 PART A: Multiple Choice Questions. 1. THERE ARE 15 QUESTIONS ON PAGES 3-7. CHECK THAT YOU HAVE THE RIGHT NUIVIBER OF QUESTIONS AND PAGES. 2. On the computd sheet, write in your student number'and bubble it in, as well as your last name and ' . ' ‘ (Hyphenated last names should bubbled in without spaces or dashes.) 3. In the Subject box, write CHM 138 and your demonstrator group number. 4. Sign your name in the Signature box. 5. ‘ Do not write ANYTHH‘IG outside of_ the boxed areas. 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 ONTHIS PAPER, BOTH OF WHICH MUST BE HANDED IN AT THE END OF THE TEST. ' ' . DURINGTHETEST: ‘ 1. Clearly circle 0n the‘ test paper the letter (a, b, c, d, or e) for the best answer you choose for each question. . r 2. 0n the computer sheet, blacken the oval which correspondsto thede you have chosen for each question. Make sure that only one answer is blackened. Fill the oval completely as indicated on the computer sheet. ‘ 3. ‘Use soft pencil only (No.2 or sofier). 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 becn collected. Page20fll Part A: Multiple Choice Questions (15 Questions, 2 Marks each) 1. A method for the stereoselective synthesis of chiral epoxides gave the product shown. below. To which faces of the doubly bonded carbons is oxygen added? HOCH; ' o )_\ _'_. HOCHZWH , C2 C3 (a) re - s: (b) re re (o) si - si (ti) si re (e) none of the above ‘ 2. Consider the molecule below. What is its degree of unsaturation? I . "Quill ‘ 2N ' ' o (3)5 ,(b)6__(°)7 (d),8 (6)9 3. Which of the nitrogen atoms in the mOIecule above are sp2 hybridized? (a) all ofthem, (b) 2, 3, 4 only ,, (c) 3, 4 only (d) 1, 2, 4 only (e) 1, 4 only 4. What is the major product of the reaction shown below? ‘ CH3 H CN NC H36 H H30 I cH2CH3 . a) i e) none of these Page3 ofll I \ 5. The following processes are applied'to cyclononatetraene: i) removal of H' ’ ii) removal of H' v iii) removal of H" Which of the above processes results in the formation of an aromatic compound? (a) i only (b) ii only (c)'iii only ((1) ii and only (6) all of these 6. Predict the major E2 product of the following maction: Ph/g/ Ph/‘\‘/H , \ H H , ' ¢ ‘ ‘ (b) * (c) ' V ‘ Ph ' ‘ H * Ph ' ‘ (a) (d) 7. What is the product of the following reaction? / . Page4ofll 8. Which of the following statements are correct about the hydration of an alkene as shown below? ‘ _ ' alkene alcohol 2. H202, OH— (i) The reaction proceeds with anti stereochemistry. (ii) Only the first step of the reaction is a reduction. _ (iii) The reaction proceeds through a carbocation _ (a) (i) only (b) (ii) only (c) (i) and (iii) only (d) (ii) (and (iii) only ‘ (e) None of the statements (i) —- (iii) are correct. - 9. Which term best describes the product (or product mixture) of the following reaction? ’ (a) achiral (b) racemic (c) meso (d) optically/active 10. Which of the following reagents and. conditions will reduce the compound below: ‘ (i) Hz/Pd onC (ii) H30: heat (iii) CrOs/HsO+, acetone (a) (i) only ('3) (ii) only , (c) (i) and (iii) only . ((1) (ii) and (iii) only . . (e) None of the reagents (i) — (iii) will reduce this compound. 0H PageSofll l 12. Which of the following molecules has peaks in its infra red spectrum in the regions of 1700 cm“ and 3500 cm"? /" 'O o o . OH , . - 4 . OCH; 0 l ‘ OH ‘ > o N Br _ , CN‘ 0H (a) (by (c) _(d) , ,(e) 13. Which of the following compounds is NOT aromatic? (a) (b) () ' I c . (d) I (e) Page60f11 14. Which of the following compounds is a product of the following reaction in its most stable conformation? ' * » Ci, H20 L I , /l (3) Wm 0’) . \ . . . HO . fl _ , c1. («9 . W01 (d) OH on t - (e) ' won 15. Which of the following reagents would be the best choice for carrying out the following reaction? (a) PCC/CHzClz (d) NaBHdethanol END OF MULTIPLE CHOICE QUESTONS Page7ofll. Part B: Short Answer Questions. (80 total mar-b) QUESTIONS MUST BE ANSWERED ON THE ANSWER SHEET FOUND AT THE END OF THE EXAM. Clear and concise answers are essential for full marks. 1. (7 marks) 1,4ecyclohexadiene reacts with bromine atoms to form the radical X' as shown below. Draw the structure of the product X'. Draw its two other important resonance forms. Use arrows to show the electron flow connecting any two of these resonance structures. ' ' . ’ .Br- , G X-»+H\Br 2. (11 marks) a) On the answer sheet, complete the chair conformers of the molecule shown below. Please note that Cl and C2 are labeled. ' ' ..-I "II" I 7/ b) In the box on the answer sheet, draw all of the possible products of the E2 reaction of the above molecule with sodium hydroxide in HZO/THF. Circle the product(s) that is (are) formed in greatest amount. * . c) Draw the product(s) that would be formed in the competing substitution reaction. 3. (6 marks) On the answer sheet, label the chiral centres R and S and draw a Newman projection of molecule A. Draw the alkene that can beused to prepare A (and its ' enantiomer) in one step? ' Page8ofll- _ (6 marks) Draw the first two propagation steps in the free radical polymerization of ‘acrylamide to polyacrylamide, initiated by hydroxide radical. Use arrows to show electron flow. - - ' r . V I V HzN _ 5. (4 marks) WhiCh reagents would you need to carryout the following transformation? I More than one step may be needed. ' . (Br \ 6. (12 marks) Draw a complete detailed 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.) ' 4 4 ‘ Page 9ofll - 7. (12 marks) a) Draw the Stereoisomeric products of thefollowing reaction. Place each stereoisomer in a box on the answer sheet. You may not need all of the boxes and wrong answers will be subtracted from right answers. 1. Hg(OAc)2, HZO/I'HF 2. NaBH4 b) Assign absolute configurations (R/S) to all of the-chirality centres in one of yo products. . . c) Once the reaction is finished, will thexresul‘ting solution rotate plane-polarized light? Provide an explanation for your answer. ' . . 8. (12 marks) Using cyclopentene as the only carbon-containing starting material, outline a synthesis for the compound shown below. You may use whatever reagents you need _ for the synthesis which occurs in several steps. Mechanisms for the individual steps in the synthesis are not required. ’ ' o I ' o Page 10 ofll 9. (10 marks) Presented below is a diagram representing the procedure that was followed in Laboratory Experiment 3 to separate a carboxylic'acid fi'om a neutral organic compound by extraction. For each of the questions a-i write your answers in the space , provided on the answer sheet. ‘ . a) What solvent was used to dissolve the solid mixture? 1 '-b)Whatwasaddedtotheresulting solution? ' aqueous organic c) What solute was contained h) What solute was contained in the aqueous layer? in the organic layer? d) What was added to the aqueous layer to recover one component of the mixture? \ e) What component of the i) By what process was this mixture was recovered?» component recovered? i) What technique was used to isolate this compound? g) What two tests or techniques were used to identify this compound? END OF THE EXAM IPagellofll 6'5 Periodic Table 'of the Elements fiwfiflflm nit-37* n“ sn- GES 52m Eun— Huua >512. 233 033 5a: 35. mus... >532. wran— mcao... a" can... a..." wagon. $ wanna? no :2 £18 5 920 was? 3: :8 r me. u. . .3. En o: . IHIIIII'IHHIIE a. mg: .5353: B Q Satay III? % N. A: 335V “ _. 8: ago; a. QM 3513.» S m» unease; P Q Q inlay 8 mcgaEzon “.820wa menu A a2 3% _ 02 :o n on... Ea N 3; "0332. :3: ENER— 233 238 co: :5 \ £5 coca—om 9.238 2? "acumaum 3% a a 3x5: Nx .h I 3&2 3 .v . 5 “5302.22 5.5302 Hahn—8 $15.5 .35 A33: ND .w A315: 3 .m .II. "$0 259 a. «soc-am 2—0 chA "t «auufim .85 :5: saw 1...... 52 2:0 :25 :2: saw is. 52 Emu ...
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This note was uploaded on 04/25/2010 for the course CHM CHM138H1 taught by Professor Browning during the Fall '08 term at University of Toronto- Toronto.

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chm138 past tests - Name: Student Number: Demo Group: I I ,...

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