Organic Chem II Spring 2008 Exam 2

Organic Chem II Spring 2008 Exam 2 - Practice Exam 2 Key....

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Unformatted text preview: Practice Exam 2 Key. Answers on last page. - PR EME CHM 202- Organic Chemistry II D41 1.C OM P d e - PR EME D41 c b a 1.C OM - PR EME D41 1.C OM 1. Which one of the following is aromatic? 2. Which one of the following annulenes is NOT aromatic? a. [6]b. [14]c. [16]d. [18]1.C OM e. [22]- - PR EME D41 3. Which of the following are aromatic? Assume all except for structure “3” are planar. N 1 - PR EME D4 11. COM a. 1, 2, 5 b. 1, 3 c. 1, 4, 5 d. 2, 5 e. 2, 4, 5 H 2 3 4 5 ED4 11. COM - PR EME D4 a. cyclopentane b. cyclopentadiene c. cyclopentadienyl cation d. cyclopentadienyl radical d. cyclopentadienyl anion 11. COM 4. The molecular orbital diagram shown depicts: - PR EM 5. Is the molecule represented in this molecular orbital diagram expected to be aromatic? COM b. no 11. a. y es ED4 Name the following compounds: 6. a. 3-sulfonlylbenzoic nitrate b. m-nitrilebenzenesulfonic acid c. m-nitrobenzenesulfonic acid d. m-sulfonylaniline e. 3-nitrobenzenesulfoxide 8. a. isopropyl methanoate b. 2-methylpropyl formate c. acetomalonic acid d. dimethylacetic anhydride e. methyl 2-methylpropanoate 7. 11. ED4 - PR EM SO3H COM 11. ED4 - PR EM COM 11. a. phenyl-orthophenylate b. o-phenylphenol c. 1,1'-dibenzanol d. o-phenoylbenzene e. phenyl benzyl alcohol O O Br a. b. c. d. e. - PR EM 3-bromonaphthalene 6-bromoanthracene 3-bromoazulene 9-bromophenanthrene 8-bromopyrene 11. ED4 MPRE M .CO 411 MED PRE OH 11. COM a. b. c. d. e. NH2 9. ED4 10. F a. 2-ethyl-6-fluoroaniline b. 6-fluoro-2-ethylaniline c. 1-ethyl-3-fluoroaniline d. 3-ethyl-1-fluoroaniline e. 1-ethyl-3-fluoro-2-nitrobenzene COM - PR EM NO2 1 N-methyl-4-bromopentanamide N- methyl-1-bromobutanamide Br N-methyl-1-bromopentanamide N- methyl-4-bromobutanamide 1- methyl-5-bromobutanamide O N H OM 1.C D41 c d Y Y H H H :B :B :B H Y :B e H Y :B D41 1.C OM - PR EME D41 Y 1.C b a OM - PR EME 12. The final mechanistic step in the electrophilic aromatic substitution reaction of benzene with electrophile, Y+, is: e d 1.C c b Br H Br 11. Br H Br - PR EME D4 H COM - PR EME D41 a OM - PR EME 13. Which of the following would be an especially stable r esonance contributor of the intermediate in the para-bromination of toluene? Br NO2 c NO2 d NO2 e NO2 Br - PR EM Br H Br H Br Br COM H ED4 11. COM b - PR EME D4 NO2 a 11. COM 14. Which of the following would be an especially unstable resonance contributor of the intermediate in the para-bromination of nitrobenzene? 11. 15. The structure shown represents the final mechanistic step in the conversion of: ED4 O O COM - PR EM a. an ether into an ester b. an ester into an acid anhydride c. a carboxylic acid into an ester d. an acid anhydride into an ester d. an ester into an acetal O - PR EM ED4 11. O COM - PR EM ED4 11. COM 16. The relative reactivity of acyl compounds toward nucleophilic substitution is: a. amide > ester > acid anhydride > acyl chloride b. acyl chloride > ester > acid anhydride > amide c. ester > acyl chloride > acid anhydride > amide d. acyl chloride > acid anhydride > ester > amide e. acid anhydride > acyl chloride > ester > amide 5 > 2 > 1 > 3> 4 2 > 5 > 3> 1 > 4 4 > 1 > 3> 5 > 2 3>2>1>4>5 4>5>2>1>3 O 1 O 2 4 411 MED PRE 5 NO2 .CO MPRE M ED4 11. COM a. b. c. d. e. - PR EM ED4 11. 17. Rank the following compounds in order of decreasing r eactivity in electrophilic substitution. In other words, from most reactive to least reactive. 2 3 Br OM 1.C D41 1 OM D41 1.C 1 2 3 equal amounts of 1 and 2 equal amounts of 1 and 3 Cl SO3H SO3 Cl - PR EME Cl 2 HO3S H2SO4 Cl Cl Cl SO3H OM Cl 3 Cl D41 1.C a. b. c. d. e. - PR EME 18. The major product(s), of the following reaction, would be: - PR EME 19. Starting from benzene, the best way to make p-nitrobenzoic acid is: 11. COM - PR EME D41 1.C OM a. HNO3/H2SO4; then CH3Cl/AlCl3; then separation of isomers; then KMnO4/ OH/heat, followed by H3O+. b. CH3Cl/AlCl3; then HNO3/H2SO4; then separation of isomers; then KMnO4/ OH/heat, followed by H3O+. c. CH3 Cl/AlCl3; then KMnO4 /-OH/heat, followed by H3O+; then HNO3/H2SO4. d. HNO3/H2SO4; then KMnO4/-OH/heat, followed by H3O+; then CH3 Cl/AlCl3. e. HNO3/H2SO4; then CO2, followed by H3O+. - PR EME D4 20. Indicate the major product. Br Br a O 11. COM b Br2 FeBr3 O c COM O - PR EME D4 O O O d O O O - PR EM ED4 11. Br O O Br COM O 11. 21. Identify the final product C in the following synthetic scheme. ED4 O Br - PR EM e COM 1. KMnO4, OH-, ∆ + SOCl2 A COM - PR EM ED4 11. 2. H3O Ph CO2Na b O O c Ph O COM - PR EM ED4 Na+ CO2e 11. d ED4 O a O O C O + (xs) H2O / H b O OH O MPRE M ED4 11. COM - PR EM 22. PhCO2-Na+ B Ph CO2Na Cl 11. a PRE MED 411 .CO c OH O OH d OH O OH OH O HO OH 3 e O OH Br OM 1.C D41 - PR EME Cl 23. Identify the final product, C, in the following synthetic scheme. 1) Fe/HCl (xs) Br2 FeBr3 2) H3PO2 C D41 Cl - PR EME NO2 Cl b c Cl d 1.C Br D41 Br Br - PR EME Br e Br PO2H NO2 - PR EME D4 11. COM a. 1 b. 2 b. 3 c. 4 O O - PR EME O 1 2 O O H O 3 OH OH 4 COM O - PR EME D4 11. 25. The hydrolysis products of the acetal in the prior question would be: b. acetic acid and methanol e. propanal and methanol c. acetone and methanol COM a. ethanal and ethanol d. acetone and ethanol b ED4 11. 26. Which compound would react most rapidly w ith NaOH? c Br COM Br d Br - PR EM a Br e Br O2N NO2 NO2 - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. NO2 NO2 PRE MED 411 .CO MPRE M ED4 11. COM 27. Indicate the reaction product. 4 PO2H NO 1.C D41 24. Which of the following is an acetal? Cl Br OM OH Cl Br OM a 1) NaNO2/HCl, O C B 1.C 2) NaOH OM A NO2 PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 O - PR EM 1) xs PhMgBr COM O 11. ED4 11. COM - PR EM ED4 11. COM - PR EME D4 11. COM - PR EME D4 11. COM - PR EME D41 HO 2) H3O+ D41 1.C OH 1) 2 equiv. NaBH4 + c a O d 1.C H H D41 a - PR EME O O OM 2) H3O - PR EME H OM HO 1.C OM O - PR EME O OH b Ph O d e O O O Ph 5 O H HO O e O Ph Ph b OH O BH2 OH HO H O HO O 28. Indicate the reaction product. c O O Ph Ph D41 1.C OM OM 1.C D41 - PR EME OM 1.C D41 - PR EME OM 1.C b. 1 c. 2 d. 3 e. 4 OM 0 1.C a. - PR EME D41 29. Treatment of m-bromotoluene with sodium amide in liquid ammonia gives rise to how many organic products? COM - PR EME D41 30. Compound A reacts with methylmagnesium bromide followed by acidification to form product B, C10H14O, with the following 1H NMR spectral data. # hydrogens splitting triplet singlet quartet singlet multiplet COM - PR EME D4 11. COM - PR EME D4 11. Compound B NMR δ Approximate integration (mm) 0.8 10 1.4 10 1.8 6 1.9 3 7.2-7.4 16 a. - PR EM ED4 11. Identify compound A. c. b. Ph d. ED4 O e. Ph Ph 11. Ph H COM H O Ph O ED4 11. COM - PR EM ED4 11. COM - PR EM O O 2. c 13. c 14. c 25. e 26. d 3. e 4. d 5. b 6. c 7. a 8. e 9. b 10. d 11. d 12. d 15. d 16. d 17. b 18. b 19. b 20. e 21. c 22. c 23. b 24. b 27. b 28. a 29. d. 30. d PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM 1. e 6 ...
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This note was uploaded on 10/09/2011 for the course CHM 202H/F taught by Professor Heller during the Fall '11 term at FIU.

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