C201HS06T2 - 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 March 9, 2006 - PR EME D41 1.C Exam 2 D41 1.C OM Name (Please Print):_KEY_ OM - PR EME ANSWERS ON LAST PAGE - PR EME D41 1.C Test Form 1 You have: - PR EME D4 11. COM To receive proper credit, please remember to bubble in your correct test form number on your Scanton. - PR EME D4 11. COM 29 questions. 100 pts total. All questions worth an equal amount. 11. COM Test taking tip: Questions are in no particular order of difficulty. Scan the exam before you begin and work through problems you’re most comfortable with first. 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 ED4 The last page contains a peri odic table and scratch page. Feel free to tear it out!! 1 - PR EME D41 1.C OM P - PR EME D41 1.C OM - PR EME constitutional isomers enantiomers diastereomers different compounds that are not isomers identical compounds 1. 1.C OM (a) (b) (c) (d) (e) D41 1.C OM Questions 1-8. For each pair of structures shown, indicate their relationship from the answer choices below. Answers can be used more than once. HO COM - PR EME D41 OH - PR EME D4 H 2. CH2 C l 11. OH F F OH H - PR EME D4 11. COM CH 2 Cl OH COM OH ED4 11. COM - PR EM ED4 11. 3. ED4 11. COM - PR EM 4. - PR EM C H3 COM H 11. 5. H F ED4 H C H3 F ED4 11. COM - PR EM H PRE MED 411 .CO MPRE M ED4 11. COM - PR EM 6. OH 7. OH C H3 H H C H3 C H3 H H C H3 OH OH 2 constitutional isomers enantiomers diastereomers different compounds that are not isomers (e) identical compounds P - PR EME D41 1.C OM - PR EME D41 1.C OM (a) (b) (c) (d) OM NH 2 D41 1.C 8. HO N H2 - PR EME D41 1.C OM - PR EME OH - PR EME D4 11. COM 9. Discodermolide, shown below, has how many chiral carbons ? OH 11. O O NH 2 OH O 11. COM - PR EME D4 O COM HO - PR EM ED4 OH c. 11 d. 12 e. 13 or more - PR EM ED4 11. COM a. 9 or less b. 10 B CH3 B C H3 PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM 10. Assign R/S configurations to carbons A and B, respectively in the compound shown below. For your convenience, the molecule is shown twice so you can do your assignments separately. C H2 C H3 C H 2C H3 A A a. R, R b. R, S H OH H OH c. S, R d. S, S HO H HO H 3 - PR EME D41 1.C OM P - PR EME D41 1.C OM 15% (-) isomer / 85% (+) isomer 85% (-) isomer / 15% (+) isomer 40% (-) isomer / 60% (+) isomer 60% (-) isomer / 40% (+) isomer none of the above 1.C OM a. b. c. d. e. - PR EME D41 1.C OM 11. The observed specific rotation of a mixture (of unknown proportions) of a pair of pure enantiomers was determined to be -10°. If the known specific rotation of the pure dextrorotatory enantiomer is +50°, what is the relative composition of the mixture? - PR EME D41 12. Assign R/S configurations to carbons A and B, respectively, in Penicillin V, shown below. For your convenience, the molecule is shown twice so you can do your assignments separately. B O S C H3 C H3 11. H - PR EME D4 O 11. COM N H H - PR EME D4 H COM A O COM O OH ED4 B A H H 11. a. R, R b. R, S c. S, R d. S, S e. can not be determined from the information given O S - PR EM O C H3 11. COM N H C H3 H - PR EM ED4 O OH 11. COM O - PR EM ED4 13. COM H Br ED4 11. pero xid es b Br c d e Br Br OR Br PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM a ? 4 OM 1.C D41 - PR EME 1.C OM - PR EME D41 1.C OM - PR EME D41 1.C OM 14. NOT GRADED P COM - PR EME D41 15. Which of the following would serve as the best synthesis of 2-bromohexane? A) - PR EME D4 11. B) - PR EME D4 11. COM C) COM D) 11. COM - PR EM ED4 11. E) All of the above would be equally suitable. ED4 11. COM - PR EM I II III IV Both III and IV PRE MED 411 .CO MPRE M ED4 11. COM - PR EM A) B) C) D) E) ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 16. Treatment of 3-methylcyclopentene with Hg(OAc)2 in THF/H2O followed by NaBH4 produces this/these product(s): 5 OM 1.C D41 - PR EME P - PR EME D41 1.C OM - PR EME D41 1.C OM 17. Which would be the best method for converting A into B? OM A) H3O+, heat - PR EME D41 1.C B) BH3/THF; then H2O2, H2O, OH- COM C) concd. H2SO4; then H2O, heat - PR EME D4 11. D) Hg(OAc)2/THF/H2O; then NaBH4 - PR EME D4 11. COM E) HBr; then NaOH/H2O 11. COM - PR EM ED4 11. COM 18. Treatment of 2-methyl-2-butene with Hg(OAc)2, in a THF-ethanol mixture, followed by NaBH4 produces which of the following as a major product? A) 11. COM - PR EM ED4 B) 11. COM - PR EM ED4 C) PRE MED ED4 411 .CO MPRE M ED4 11. COM - PR EM E) 11. COM - PR EM ED4 D) 6 - PR EME D41 1.C OM P 1 . Hg (O Ac) 2/ TH F/H 2O 1 -bu ten e 1.C OM 2. Na BH 4 D41 C) - PR EME D41 2 . Na OH , H 2O 2, H 2O OM 1 . BH 3/TH F 1 -bu ten e 1.C B) - PR EME D41 1.C OM 19. Which of the following would be a reasonable synthesis of CH3CH2CH2CH2OH? A) 1 . H3 O + , 1 -bu ten e 11. COM - PR EME D) More than one of these E) None of these - PR EME D4 20. How many different mono-alkenes (compounds containing one double bond) would yield methylcyclopentane when treated with H2/Pt ? c. 3 d. 4 e. none of the above COM b. 2 COM - PR EME D4 11. a. 1 ED4 11. 21. Which of the following has the smallest heat of hydrogenation (i.e., least negative COM - PR EM enthalpy of hydrogenation)? b. c. d. 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. a. 7 - PR EME D41 1.C OM P - PR EME OM 1.C D41 H20, H2SO4, heat 1. BH3/THF 2. NaOH, H2O2, HO1. Hg(OAc)2, H2O/THF; 2. NaBH4 HBr, CH3OH OM - PR EME (a) (b) (c) (d) D41 1.C OM For each of the following reactions, the major product is shown. Indicate the preferred reagent(s)/condition(s). Answer choices can be used more than once. OH - PR EME D41 1.C 22. COM OH OH COM - PR EME D4 11. 23. ED4 11. COM - PR EM ED4 11. COM - PR EME D4 11. 24. COM - PR EM 25. The compound, cis-1,2-diethylcyclopropane contains ___________ carbons, but overall is a(n) _____________ molecule. chiral, chiral chiral, achiral no chiral, chiral no chiral, achiral PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. a. b. c. d. 8 - PR EME D41 1.C OM P OM - PR EME D41 1.C OM 26. For the reaction of 2-methylpropene with HBr in the presence of peroxides, which of the following is a correct depiction of a propagation step of the major reaction pathway? D41 1.C a. H + Br Br OM Br + Br - PR EME H COM - PR EME D41 1.C b. - PR EME D4 11. c. Br - PR EME D4 11. COM Br Br Br 11. COM d. ED4 11. COM - PR EM ED4 27. For the reaction of 2-methylpropene with HBr in solvent methanol, which of the following is a correct depiction of a step in the major reaction pathway? H Br H + Br B r- - PR EM ED4 11. COM - PR EM a. c. + B r- H O C H3OH d. C H3OH H O PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM b. 9 - PR EME D41 1.C OM P - PR EME D41 1.C OM 28. For the reaction of 2-methylpropene with Br2 in solvent H2O, which of the following is a correct depiction of a step in the major reaction pathway? D41 - PR EME Br OM Br H OH - PR EME D41 1.C O H2 OH 2 COM Br H OH Br COM - PR EME D4 11. c. Br 11. Br - PR EME D4 d. B r- + Br 1.C Br b. Br OM a. H OH 11. COM OH 2 COM - PR EM ED4 29. For the reaction of 2-methylpropene with Br2 in solvent CH2Cl2, which of the following is a correct depiction of a step in the major reaction pathway? 11. Br ED4 a. Br + B r- + Br- + Br- 11. COM - PR EM Br ED4 Br - PR EM b. Br ED4 11. COM Br Br - PR EM c. Br Br d. Br Br Br Br + B r- PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM Br 10 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 ED4 11. COM - PR EM ED4 11. COM - PR EME D4 11. COM - PR EME D4 11. COM - PR EME D41 1.C OM - PR EME D41 1.C OM - PR EME P 1. e 2. b 3. b 4. a 5. b 6. c 7. e 8. c 9. e 10. d 11. d 12. b 13. a 14. NOT GRADED 15. b 16. e 17. d 18. b 19. b 20. d 21. c 22. c 23. b 24. a 25. b 26. c 27. d 28. c 29. a 11 D41 1. ...
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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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