C201H S10 T2 Key

C201H S10 T2 Key - CHM 201 Organic Chemistry I Answers on...

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Unformatted text preview: CHM 201- Organic Chemistry I Answers on last page. Exam 2 Key Questions 1-8. For each pair of structures shown, indicate their relationship from the answer choices below. Answers can be used more than once. (a) (b) (c) (d) constitutional isomers enantiomers diastereomers different compounds that are not isomers (e) identical compounds 1. 2. HO OH P OH H CH2 C l F F CH 2 Cl OH H OH 3. 4. C H3 H F 5. H 6. H C H3 H F OH 7. OH OH C H3 H H C H3 C H3 H H C H3 OH NH 2 8. OH OH HO N H2 9. D iscodermolide, shown below , has how many chiral carbons? HO O O OH O NH 2 OH O OH a. 9 or less b. 10 c. 11 d. 12 e. 13 or more 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. a. R, R b. R, S c. S, R d. S, S C H 2C H3 A H B H OH HO OH HO H CH3 C H2 C H3 A B H C H3 1 11. The observed specific rotation of a mixtur e (of unknown proportions) of a pair of pure enantiomers was determined to be -10°. If the known specific rotation of the pure dex trorotatory enantiomer is +50°, what is the relative composition of the mixtur e? a. b. c. d. e. 15% (-) isomer / 85% (+) isomer 85% (-) isomer / 15% (+) isomer 40% (-) isomer / 60% ( +) isomer 60% (-) isomer / 40% (+) isomer none of the above 12. Assign R /S configur ations to carbons A and B, respectively , in Penic illin V, shown below. For your convenience, the molecule is show n twice so you can do your assignments separately . O O B A H H C H3 N H C H3 H O H H S O S O B A C H3 N H C H3 H O O OH O OH a. R , R b. R , S c. S, R d. S , S e. can not be determined from the information given 16. Treatment of 3- methy lcyclopentene with H g(OAc)2 in THF/H2O followed by N aBH4 produces this/these produc t(s): A) B) C) D) E) I II III IV Both III and IV 2 17. Which w ould be the best method for conver ting A into B? A) B) C) D) E) + H3O , heat BH3/THF; then H2O2, H2O, OH concd. H2SO4; then H2O, heat Hg(OAc)2/TH F/H2O; then NaBH4 HBr; then NaOH /H2O 18. Treatmen t of 2-methy l-2-butene w ith Hg(OA c)2, in a TH F-ethano l mix ture, follow ed by N aBH4 produces which of the fo llow ing as a major product? a. b. c. d. e. 19. Which of the following would be a reasonable synthesis of CH3CH2C H2CH2OH? A) 1 . H O +, ∆ 1 -bu ten e B) 1 -bu ten e C) 1 -bu ten e 3 1 . BH 3/TH F 2 . Na OH , H 2O 2, H 2O 1 . Hg (O Ac) 2/ TH F/H 2O 2. Na BH 4 D) More than one of these E) None of these 20. Ignoring stereoisomers, how many different mono-alkenes (compounds containing one double bond) would yield methylcyclopentane w hen treated with H2/Pt? a. 1 b. 2 c. 3 d. 4 e. none of the above 21. Which of the following has the smallest heat of hydr ogenation (i.e., leas t negative enthalpy of hydrogenation)? a. b. c. d. 3 For each of the follow ing r eactions, the major produc t is shown. Indicate the preferred reagent(s)/condition(s). Answer choices can be used more than once. ( a) ( b) (c ) ( d) H20, H2SO4, heat 1. BH3/TH F 2. NaOH, H2O2, H2O 1. H g(OAc)2, H2O/TH F; 2. NaBH4 HBr, CH3OH OH 22. OH 23. OH 24. 25. The compound, cis-1,2-diethy lcyclopropane contains ___________ carbons , but overall is a(n) _____________ molecule. a. b. c. d. chiral, chiral chiral, achiral no chiral, chiral no chiral, achiral 27. For the reac tion of 2- methylpropene w ith H Br in solvent methanol, which of the follow ing is a correct depiction of a s tep in the major reaction pathway? a. H H + Br Br B r- b. c. d. + H O C H3OH C H3OH B r- H O 4 28. For the reac tion of 2- methylpropene w ith Br2 in solvent H2O, which of the following is a correct depiction of a s tep in the major reac tion pathway? Br a. Br + Br Br B r- Br b. H OH O H2 Br OH 2 c. H OH Br Br Br d. H OH OH 2 29. For the reac tion of 2- methylpropene w ith Br2 in solvent CH2Cl2, w hich of the following is a correct depiction of a s tep in the major reaction pathway? Br a. Br Br Br b. Br Br Br c. Br Br Br d. + B r- + Br- + Br- Br Br Br 1. e 2. b 3. b 4. a 5. b 6. c 7. e 8. c 9. e 13, 14 & 15 deleted 16. e 17. d 18. b 19. b 20. d 24. a 25. b 26. deleted 27. d 28. c 29. a Br + B r- 10. d 11. d 12. b 21. c 22. c 23. b 5 ...
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