Organic Chemistry II Lecture Fall 2017 - Final Exam

1 Professor: Dr. George X. Thyvelikakath Your Name__________________________ Please Print ORGANIC CHEMISTRY II LECTURE FALL 2017 - FINAL EXAM Total Points: 200 __ Your Score: ________ “As a student of ORU, I hereby pledge my full and hearty support to the Honor Code. I agree not only to be honest to myself but to report all cases of dishonesty that are observed by me.” I, (sign your name here), agree to be honest in every way before, during, and after this exam. 1. How many 13CNMR signals does the following compound exhibit? A) B) C) D) 2. What is the correct assignment of the number of signals in the 13C NMR spectra of the following disubstituted benzene derivatives? A) B) C) D) 3. 4 5 6 8 I = 3 signals; II = 3 signals; III = 2 signals. I = 3 signals; II = 4 signals; III = 2 signals. I = 6 signals; II = 6 signals; III = 6 signals. I = 3 signals; II = 4 signals; III = 3 signals. Which of the following is not one of the Hückel's criteria for aromaticity? A) The molecule must be cyclic. B) The molecule must be planar. C) The molecule must be completely conjugated. D) The molecule must have 4n pi electrons. 2 4. Which of the following ions is aromatic? A) B) C) D) 5. Which of the following molecules has the most acidic hydrogen atoms? A) B) C) D) 6. I II III IV Rank the following compounds in order of decreasing acidity, starting with the most acidic. A) B) C) D) 7. I II III IV I > II > III III > II > I III > I > II I > III > II Which of the following ions is aromatic? A) B) C) D) Only I and II Only II and III Only III and IV Only II and IV 3 8. What is the name of the following compound? A) B) C) D) 9. What is the name of the following compound? A) B) C) D) 10. meta-bromophenol para-hydroxybenzene 3-bromoanisole 6-methoxy-2-bromobenzene What is the correct structure for aniline? A) B) C) D) 11. 2,6-dimethylbenzene 5-methyltoluene anisole 1,3-dimethylbenzene I II III IV What is the major organic product obtained from the following reaction? A) I B) II C) III D) IV 4 12. What is the major organic product obtained from the following reaction? A) I 13. C) III D) IV What is the major organic product obtained from the following reaction? A) I 14. B) II B) II C) III D) IV What is the major organic product obtained from the following reaction? A) I B) II C) III D) IV 5 15. What is (are) the product(s) of the following reaction? A) Only I 16. C) Only III D) Only I and III What is (are) the product(s) of the following reaction? A) Only I 17. B) Only II B) Only II C) Only III D) Only I and II Rank the following compounds in order of increasing reactivity in electrophilic aromatic substitution. A) I < II < III < IV C) B) D) II < I < III < IV II < I < IV < III III < IV < I < II 6 18. 19. 20. Rank the following compounds in order of decreasing reactivity in electrophilic aromatic substitution. A) II > IV > I > III C) B) D) IV > I > II > III II > III > IV > I IV > II > I > III Rank the following activating groups in order of decreasing strength of activation, listing the most activating first. A) IV > II > III > I C) B) D) II > IV > III > I II > III > IV > I III > IV > II > I Rank the following deactivating groups in order of increasing deactivating strength, listing the least deactivating first. A) I < II < III < IV C) B) D) IV < III < I < II II < III < IV < I II < I < III < IV 7 21. What are the product(s) of the following reaction? A) Only I 22. B) Only II D) Only III What are the product(s) of the following reaction? A) Only I and II 23. C) Only I and II B) Only I and III C) Only II and III What is the major product of the following reaction? A) I B) II C) III D) IV D) Only IV 8 24. What are the two distinct pathways for nucleophilic aromatic substitution? A) Addition-substitution and substitution-addition B) Addition-elimination and elimination-addition C) Addition-addition and elimination-elimination D) Elimination-substitution and substitution-elimination 25. What is the reactive intermediate formed in the addition-elimination mechanism of nucleophilic aromatic substitution? A) Carbocation B) Radical C) Benzyne D) Carbanion 26. What is the reactive intermediate formed in the elimination-addition mechanism of nucleophilic aromatic substitution? A) Carbocation B) Radical C) Benzyne D) Carbanion 27. Rank the following compounds in order of increasing reactivity in nucleophilic aromatic substitution. A) III < II < I 28. B) I < II < III C) III < I < II D) I < III < II What is the major product of the following reaction? A) I B) II C) III D) IV 9 29. Which aryl fluoride reacts the fastest with NaOH? A) I 30. 32. C) III D) IV In addition to the product shown, what other product is formed in the following reaction? A) I 31. B) II B) II C) III D) IV Rank the labeled protons (Ha-Hd) in order of increasing acidity, starting with the least acidic. A) Ha < Hb < Hc < Hd C) B) D) Hb < Hc < Hd < Ha Hb < Hc < Ha < Hd Hd < Ha < Hc < Hb Rank the following compounds in order of decreasing acidity, putting the most acidic first. A) IV > III > I > II C) II > I > IV > III 10 B) 33. 34. 35. IV > II > I > III D) II > I > III > IV Rank the following compounds in order of increasing acidity, putting the least acidic first. A) II < III < I < IV C) B) D) IV < I < II < III II < I < III < IV IV < III < I < II Rank the following compounds in order of increasing acidity, putting the least acidic first. A) III < II < IV < I C) B) D) I < II < III < IV III < IV < II < I I < IV < II < III Rank the following compounds in order of decreasing acidity, putting the most acidic first. A) IV > III > II > I C) B) D) IV > II > III > I IV > I > III > II I > II > III > IV 11 36. 37. 38. Rank the following compounds in order of increasing acidity, putting the least acidic first. A) I < II < III < IV C) B) D) I < IV < III < II III < II < I < IV IV < I < II < III Rank the following compounds in order of decreasing acidity, putting the most acidic first. A) III > IV > I > II C) B) D) IV > III > II > I IV > III > I > II I > II > III > IV What physical property and reaction type are used by extraction as useful techniques to separate and purify mixtures of compounds? A) Physical property = solubility differences; reaction type = acid-base reaction. B) Physical property = boiling point; reaction type = acid-base reaction. C) Physical property = solubility differences; reaction type = oxidation-reduction. D) Physical property = density; reaction type = oxidation-reduction. 39. What would happen if a mixture of benzoic acid (C6H5COOH) and NaCl is added to a separatory funnel containing H2O and CH2Cl2? A) The benzoic acid would dissolve in the water layer and the NaCl would dissolve in the organic layer. B) The benzoic acid would dissolve in the organic layer and the NaCl would dissolve in the water layer. C) Both benzoic acid and NaCl would dissolve in the organic layer. D) Both benzoic acid and NaCl would dissolve in the water layer. 12 40. 41. Rank the following compounds in order of increasing acidity, putting the least acidic compound first. A) III < I < II < IV C) B) D) II < IV < I < III What is the product of the following reaction? A) I 42. IV < I < II < III B) II C) III D) IV What is the product of the following reaction? A) I B) II C) III D) IV III < II < I < IV 13 43. What will be the product of the following reaction (before any aqueous work-up)? A) I 44. B) II C) III D) IV Why would the alcohol in the following compound need to be protected before reaction? A) If it isn't protected, the product will be a carboxylic acid. B) The Grignard reagent will react with the alcohol before the ketone. C) Magnesium is Lewis acidic and will coordinate with the alcohol. D) There is no need to protect the alcohol. 45. What is the purpose of a silyl ether? A) To protect esters from organometallic reagents and other reagents B) To protect ketones from organometallic reagents and other reagents C) To protect alcohols from organometallic reagents and other reagents D) To prevent the formation of carboxylic acids 14 46. What is the major organic product of the following reaction? A) I 47. B) II C) III D) IV Which of the following statements about organometallic reagents is not true? A) Organometallic reagents contain a carbon atom bonded to a metal. B) C) The more polar the carbon-metal bond, the more reactive the organometallic reagent. Organometallic reagents react as bases and nucleophiles. D) Organometallic reagents are strong acids that readily donate a proton to water. 48. What is the major organic product of the following reaction? A) Only I 49. B) Only II C) Only III D) Only I and II What carbonyl compound and Grignard reagent could be used to prepare 2-butanol? A) Only I B) Only II C) Only III D) Only I and II 15 50. What is the major organic product in the following sequence of reactions? A) I B) II C) III D) IV