C201HS06T3 - OM 1.C D41 - PR EME P OM CHM 201- Organic...

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Unformatted text preview: OM 1.C D41 - PR EME P OM CHM 201- Organic Chemistry I April 25, 2006 - PR EME D41 1.C Exam 3 D41 1.C OM Name (Please Print):____KEY____ OM - PR EME ANSWERS ON LAST PAGE. - PR EME D41 1.C You have: → Test Form 1 ← - PR EME D4 11. COM - PR EME D4 11. COM To be properly graded, you must bubble in your correct Test Form number on your Scantron! ED4 11. COM The last sheet is a scratch page and periodic table. You can rip it out after we tell you to begin! PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM 29 questions. 100 pts total. All questions worth an equal amount. 1 OM - PR EME D41 1.C OM P C) III D) IV 11. B) II E) None of the above - PR EME D4 A) I COM - PR EME D41 1.C OM - PR EME D41 1.C OM - PR EME D41 1.C 1. Which would be the major product of the following reaction? - PR EME D4 11. COM 2. Which alkyl halide would give the highest yield of the elimination product when treated with sodium ethoxide in ethanol? A) CH3CH2Br D) E) - PR EM ED4 11. COM B) CH3CH2CH2Br - PR EM ED4 11. COM C) CH3CH2CH2CH2Br A) I B) II C) III D) IV E) An equimolar mixture of I and II PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM 3. What would be the major product of the following reaction? 2 OM 1.C D41 - PR EME 1.C OM P OM - PR EME D41 1.C OM - PR EME D41 4. Which alkyl halide would you expect to undergo SN1 hydrolysis most rapidly? A) (CH3)3CI (1-iodo-1,1-dimethylethane) D) (CH3)3CF B) (CH3)3CBr E) They would all react at the same rate. C) (CH3)3CCl COM - PR EME D4 11. COM - PR EME D41 1.C 5. Which nucleophilic substitution reaction is not likely to occur? A) I- + CH3CH2–Br → CH3CH2–I + BrB) I- + CH3CH2–OH → CH3CH2–I + OHC) CH3O- + CH3CH2–Br → CH3CH2–OCH3 + BrD) OH- + CH3CH2–Cl → CH3CH2–OH + ClE) None of the above (in other words, all are likely to occur). - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EME D4 11. 6. What would be the major product of the following reaction? B) II C) III D) IV E) Equal amounts of I and III PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM A) I 3 - PR EME D41 1.C OM P E) D41 1.C OM - PR EME D41 1.C OM 7. Which alkyl chloride, though primary, is essentially unreactive in SN2 reactions? D) A) CH3CH2CH2CH2CH2CH2Cl 1.C OM - PR EME B) - PR EME D4 11. COM - PR EME D41 C) 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EME D4 11. COM 8. Which would be formed in the following reaction? B) II C) III D) IV E) All of the above would be formed to some extent PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 A) I 4 OM 1.C D41 - PR EME P B) II C) III D) IV E) None of these ED4 11. COM A) I - PR EME D4 11. COM - PR EME D4 11. COM - PR EME D41 1.C OM - PR EME D41 1.C OM - PR EME D41 1.C OM 9. What would you expect to be the chief organic product(s) when tert-butyl bromide reacts with sodium acetylide, i.e., COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM 10. What is the major product of the following reaction? B) II C) III D) IV E) V PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. A) I 5 OM 1.C D41 1.C OM - PR EME C) III D) Equal amounts of I and II COM B) II E) No E2 reaction will occur. COM - PR EME D4 11. A) I - PR EME D4 11. COM - PR EME D41 1.C OM - PR EME D41 1.C OM - PR EME D41 11. Predict the major elimination product. P - PR EM ED4 11. COM - PR EM ED4 11. 12. Which reaction would be expected to take place most rapidly in polar aprotic solvent? Assume concentrations of the reactants and the temperature are the same in each instance, and that nucleophilicity in polar aprotic solvent follows the same trend as observed in the gas phase, in other words, parallels basicity. A) CH3S¯ + CH3–I → CH3SCH3 + I¯ 11. COM B) ED4 C) COM - PR EM CH3O¯ + CH3–I → CH3OCH3 + I¯ CH3S¯ + CH3–Cl → CH3SCH3 + Cl¯ PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM E) - PR EM ED4 11. D) 6 - PR EME D41 1.C OM P B) II C) III D) Only two of the above E) All of the above 11. COM A) I - PR EME D41 1.C OM - PR EME D41 1.C OM - PR EME D41 1.C OM 13. Which compound(s) would be produced by the following reaction? - PR EME D4 Questions 14-15. Consider the following reaction scheme. CH A - PR EME D4 11. COM 1 . 1 e q u iv . N a C 2 . H2 , L in d l ar c a t al y s t Na OH B COM 3 . B H3 /T HF Br ED4 11. 4 . H2 O 2, OH -, H2 O COM - PR EM 14. Indicate the structure of B in the scheme above. b. 11. a. d. O e. ON a O - PR EM ED4 O c. - PR EM ED4 11. COM OH 11. COM 15. Indicate the structure of A in the scheme above. ED4 a. COM - PR EM b. B r Br Br Br d. Br Br e. Br Br Br PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. Br c. 7 - PR EME D41 1.C OM P D41 1.C OM 16. Choose the best option for the following transformation. O D41 1.C OM - PR EME ? 1 . N aNH 2 2. CH 3(CH 2) 5Br 3 . H gS O4, H 2SO 4, H2O b. 1 . Hg SO 4, H2S O4, H 2O 2. N aN H2 3. C H3(C H2)5Br c. 1 . Na NH 2 2 . CH 3CH2B r 3 . N aNH 2 4 . CH 3(CH 2)3Br 5. H 2SO 4, H2O - PR EME D41 1.C OM - PR EME a. d . 1 . Na NH 2 2. CH 3( CH 2) 2B r 3 . N aN H2 4 . C H3(CH 2)2Br 5. H 2SO 4, H2O COM Non e o f th e a bo ve - PR EME D4 11. COM - PR EME D4 11. e. COM 17. The SN1 pathway for the following reaction produces the products shown. CH 3 CH 3 - PR EM ED4 11. CH 3 + ED4 SN 1 OC H3 A OC H3 B 11. COM - PR EM Br 11. COM C H3 O H - PR EM ED4 Which is a true statement? PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM a. A and B are formed in an equal amount b. A is formed in greater than 50% because bromine and methyl groups in the starting material prefer an equatorial orientation c. B is formed in greater than 50% because bromine and methyl groups in the starting material prefer an equatorial orientation d. A is formed in greater than 50% because dissociation of Br- partially blocks approach of the nucleophile e. B is formed in greater than 50% because dissociation of Br- partially blocks approach of the nucleophile 8 - PR EME D41 1.C OM P 1.C CH 3 OM 18. Predict the major product. - PR EME D41 H C H3OOM ? 1.C E2 c. OM b. - PR EME D4 11. COM e. d. - PR EME D41 1.C a. - PR EME D41 Br H 11. COM 19. Rank the following compounds from highest to lowest pKa. O - PR EME D4 OH COM + II III 11. I > II > III II > I > III III > II > I I > III > II II > III > I COM - PR EM ED4 I ED4 11. COM - PR EM ED4 a. b. c. d. e. _ 11. N O OH OH ED4 11. COM - PR EM 20. All of the following answer choices are valid resonance structures of the structure shown at top in brackets, except: - PR EM o th e r re s o n an c e co n tr ib u to r s ED4 11. COM + c. - PR EM a. + d. ED4 MPRE M b. 11. COM + + + PRE MED 411 .CO e. N o n e o f t h e a b o v e. A ll o f th e a n s we r ch o ic es ar e v a lid r e s o n an c e s t ru c tu r es f o r th e s tr u ctu r e at t o p . 9 - PR EME D41 1.C OM P H2 1.C OM 21. D41 ? OM c. 1.C b. d. C H3 C H2 CH 3 C H3 CH 2 C H 3 C H 2C H 3 C H 2C H 3 C H3 1.C OM CH3 - PR EME D41 a. - PR EME Pt / C COM - PR EME D41 e . M o r e th a n o n e o f t h e a b o v e . - PR EME D4 11. COM - PR EME D4 11. 22. For your convenience, the answers are shown in Newman, sawhorse, and perspective projections. So, within any given box, you are looking at three projections of the exact same molecule. Focus on whatever projection(s) is/are easiest for you to see. H2 ? 11. COM Pd/ C ED4 I - PR EM II Et COM Et Me Et Me Pr Me Me Me Et Pr Pr H H Me H H Pr COM 11. Pr Me ED4 11. Et - PR EM Et Me Pr Pr Et Me Me Me Pr Et H H H Me Pr Me H Me Et H H H Me H H Me H Me Et Pr Me H H H Me H 11. COM H Pr Et ED4 COM H H Me - PR EM H Me H Me Et Me H - PR EM Me ED4 11. Pr IV III PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 a. I and II b. III and IV c. I and IV d. II and III e. II and IV 10 - PR EME D41 1.C OM P 1.C OM 23. D41 C l2 - PR EME ? 1.C OM C H2C l2 - PR EME D41 I OM Cl Et II I Cl Et Cl Me Me Me Me Et Me - PR EME Et D41 1.C Me II Cl Me COM Me Et Cl Me Cl Et Cl Cl Me Me Et Me Et Cl Me Et Me Et Me Et Cl Cl Et Cl 11. COM Me - PR EME D4 Et 11. Me Cl Me Cl - PR EME D4 Cl Et Cl Et 11. Cl Et Cl COM Et Et - PR EM ED4 11. COM - PR EM ED4 a. I b. II c. III d. I and II e. II and III 11. COM 24. Indicate the best method to prepare 3-hexyne, starting from (Z)-3-hexene. H2, Pd/C Na / liquid NH3 1. Br2 / CH2Cl2; 2. 1 equiv. NaNH2 1. Br2 / CH2Cl2; 2. excess NaNH2 1. BH3, 2. H2O2, OH-, H2O; 3. acetylene, NaNH2 - PR EM ED4 11. COM - PR EM ED4 a. b. c. d. e. 11. COM 25. The π-molecular orbital of 1,3-butadiene s hown at right is: non-bonding / HOMO bonding / HOMO bonding / LUMO anti-bonding / HOMO anti-bonding / LUMO PRE MED 411 .CO MPRE M ED4 11. COM a. b. c. d. e. - PR EM ED4 _____________, and would be considered the _____________ of the ground-state configuration of the molecule. 11 - PR EME D41 1.C OM P OM - PR EME D41 1.C OM 26. Indicate the total number of resonance structures for the structure shown, including the structure shown. In other words, if there are no more resonance structures, your answer would be 1, if one more, your answer would be 2, and so on. 1.C d. 4 e. 5 - PR EME c. 3 OM b. 2 - PR EME D41 1.C a. 1 ? D41 + COM 27. Which is a correct IUPAC name? 4-heptyne 2-ethyl-3-hexyne 2,3-dimethyl-5-octyne 2,5-dimethyl-3-hexyne None of the above (in other words, all are correct IUPAC names) - PR EME D4 11. COM - PR EME D4 11. a. b. c. d. e. 2. H H OH CH3 - PR EM 1. ED4 11. COM 28. What products would be obtained from the hydroboration-oxidation of 1methylcylohexene? 5. H OH H OH H H OH OH CH 3 H H C H3 CH 3 H - PR EM COM CH 3 COM - PR EM ED4 11. 1, 2 1, 3 2, 3 3, 4 4, 5 11. a. b. c. d. e. ED4 11. COM H 4. 3. C H3 a. b. c. d. e. 1, 1 >1, 1 1, >1 >1, >1 None of the above C H3 Cl PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 29. When the following stereoisomer of 2-chloro-1,3-dimethylcyclohexane reacts with methoxide ion in a solvent that encourages E2/SN2 reactions ________ E2/SN2 product(s) is(are) formed. When the same compound reacts with methoxide ion in a solvent that encourages E1/SN1 reactions ________ E1/N1product(s) is(are) formed. 12 PRE MED 411 .CO MPRE ME D41 1.C OM - PR EME D41 1.C OM - PR EME D41 1.C OM - PR EME D41 1.C OM - PR EME D41 1.C OM - PR EME D41 1.C OM - PR EME D41 1.C OM - PR E MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO 1. c 2. e 3. b 4. a 5. b 6. c 7. e 8. e 9. b 10. d 11. b 12. c 13. e 14. b 15. e 16. d 17. e 18. a 19. e 20. d 21. e 22. a 23. e 24. d 25. e 26. a 27. d 28. e 29. c MPRE MED P 13 411 .CO M ...
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This note was uploaded on 11/05/2011 for the course CHM 201 taught by Professor Colonna during the Fall '08 term at University of Miami.

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