A. IV > III > II > I B. IV > II > III > I C. III > IV > II > I D. III > IV > I > II
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1 Practice Final Exam, Chemistry 2220, Organic Chemistry II 1. Rank the designated protons by 1 H NMR chemical shift ( ), highest first. A. IV > III > II > I B. IV > II > III > I C. III > IV > II > I D. III > IV > I > II 2. What are the products, if any, expected from the following reaction? 3. What is the IUPAC name for the following compound? A. cis-1,2-cyclopentanediol B. meso-1,2-cyclopentanediol C. (1R,2R)-1,2-cyclopentanediol D. (1R,2S)-1,2-cyclopentanediol 4. Which statement explains why cyclohexanol has a pk a of 18 and phenol has a pk a of 10? A. Phenolate is a stronger base than the conjugate base of cyclohexanol. B. The conjugate base of cyclohexanol is resonance stabilized. C. The conjugate base of phenol is resonance stabilized. D. Phenol is a weaker acid than cyclohexanol. 5. Which one of the following compounds is NOT a product of the reaction between 1,3- butadiene and HBr? A. (S)-3-bromo-1-butene B. (R)-3-bromo-1-butene C. (Z)-2-bromo-2-butene D. (E)-1-bromo-2-butene 345
2 6. Predict the product of the following reaction. 7. Choose the reagents necessary to carry out the following conversion. A. 1. HBr; 2. NaOH/heat; 3. H 3 O + ; 4. PCC B. 1. Br 2 /light; 2. EtONa; 3. BH 3 -THF; 4. H 2 O 2 /NaOH; 5. PCC C. 1. Br 2 /FeBr 3 ; 2. NaOH; 3. BH 3 -THF; 4. H 2 O 2 /NaOH; 5. CrO 3 /H 2 SO 4 D. 1. NBS/light; 2. (CH 3 ) 3 CONa; 3. H 3 O + /heat; 4. PCC 8. Which one of the following compounds is aromatic? 9. Predict the product for the following reaction. A. ethyl-3-methylbutanoate B. ethyl-2-methylpropanoate C. isobutylethanoate D. 5-methyl-3-hexanone 346
3 10. Predict the product for the following reaction. 11. Rank the following carboxylic acid derivatives in decreasing order (most to least) of reactivity towards nucleophilic acyl substitution. A. I > IV> III > II B. II > III > I > IV C. IV > I > III > II D. III > I > II > IV 12. Predict the product for the following reaction sequence: 13. Amino acids are connected to each other by. A. an ether linkage B. an acetal linkage C. an ester linkage D. an amide linkage 347
4 14. Predict the product for the following reaction. 15. Rank the following compounds in decreasing order of basicity, strongest to weakest. A. III > IV> I > II B. I > II > IV > III C. IV > III > I > II D. IV > I > II > III 16. Predict the product for the following reaction sequence. 348
5 17. Predict the product for the following reaction sequence. 18. Which of the following D-aldoses will produce an optically inactive product when treated with NaBH 4 /H 2 O? 19. What is the pi of the following amino acid? A B C D Which one of the following is the correct structure for polyisobutylene? 349
6 21. Please choose an appropriate oxidizing reagent for the following reaction. A. LiAlH 4 B. H 2 /Pt C. PCC D. H 2 CrO Which of these compounds best fits these data? It is soluble in water, and turns red litmus blue. It has only one major IR band, at 2950 cm -1, and has the following 1 H NMR spectrum: 2.7 ppm, 2H; 2.2 ppm, 6H; 1.0 ppm, 3H. A. N,N-dimethylethanamine B. propanoic acid C. 2-propanol D. 2-methylpropane 23. What is the major product for the following reaction? A. B. C. D. 24. Which position is most likely to undergo an EAS reaction? A. B. C. D. 350
7 25. How would you convert an unsaturated fatty acid into a saturated fatty acid? A. KMnO 4, - OH, heat B. - OH, H 2 O, heat; then H 3 O + C. H 2, Ni, pressure D. H 3 O +, H 2 O, heat 26. What structure has the following proton NMR spectrum? 1 H NMR: doublet, 6.6 ppm, 2H doublet, 7.8 ppm, 2H broad singlet, 4.2 ppm, 2H singlet, 2.1 ppm, 3H A. B. C. D. 27. Which of the following is the correct synthesis of the compound shown? A. B. C. D. 351
8 28. Which is the correct intermediate for the major product of following reaction? A. B. C. D. 29. Which of the following molecules has the lowest boiling point? A. CH 3 CH 2 CH 2 NH 2 B. CH 3 CH 2 NHCH 3 C. (CH 3 ) 3 N D. (CH 3 ) 3 NHCl 30. Starting from benzene, what is the correct synthesis of the compound below? A. B. C. D. 31. What is the major product for the following reaction? A. B. C. D. 352
9 32. What is the IUPAC name for the following compound? A. 1-methyl-N-butyl-1-butanamine B. 4-methyl-5-octanamine C. 1-ethyl-N-propyl-1-pentanamine D. N-propyl-2-pentanamine 33. A pentapeptide has the molecular composition: Arg, Glu, Ile, Phe, Leu. After partial hydrolysis, the fragments are: Glu-Ile, Leu-Arg, Phe-Leu, Arg-Glu. What is the sequence? A. Phe-Leu-Arg-Glu-Ile B. Ile-Glu-Arg-Leu-Phe C. Arg-Glu-Ile-Phe-Leu D. Phe-Leu-Glu-Ile-Arg 34. Predict the product for the following reaction. 35. What is the product of the following reaction? 353
10 36. Which of the following compounds is able to undergo a self-aldol condensation? A. phenylethanal B. formaldehyde C. benzaldehyde D. 2,2-dimethylpropanal 37. The best synthesis of 1,4-dimethyl-2-nitrobenzene is: 38. Which of these is the most reliable way to make 3-heptene? A. CH 3 CH 2 CHBrCH 2 CH 2 CH 2 CH 3 + NaOCH 3, heat B. CH 3 CH 2 CH=O + Ph 3 P=CHCH 2 CH 2 CH 3 C. CH 3 CH 2 CHOHCH 2 CH 2 CH 2 CH 3 + H 2 SO 4, heat D. CH 3 CH 2 C CCH 2 CH 2 CH 3 + H 2 /Pt 39. Predict the major product for the following reaction. 354
11 40. Please indicate the # of signals in the 13 C NMR and 1 H NMR spectra for the following compound: A C NMR and 4 1 H NMR B C NMR and 7 1 H NMR C C NMR and 4 1 H NMR D C NMR and 5 1 H NMR 41. What is the major product of this reaction? 42. Predict the product of the following reaction. 355
12 43. What is the IUPAC name for: A. 5-hydroxy-2-phenyl-3-hexanone B. 2-hydroxy-5-phenyl-4-hexanone C. 2-hydroxypropyl-1-phenylethylketone D. 5-hydroxy-3-keto-2-phenylhexane 44. Which step is not part of the base-catalyzed aldol condensation mechanism? 356
13 45. Which is true for aromatic but not antiaromatic compounds? A. Are cyclic and planar B. Are monocyclic C. Have a conjugated system with p orbital at every vertex D. Satisfy Hückel s rule 46. What is the major product of this reaction? 47. A compound with the molecular formula C 8 H 14 O 4 shows an IR band at 1740 cm -1 but not cm -1. The proton NMR spectrum consists only of a triplet at 1.3 ppm, a triplet at 2.6 ppm and a singlet at 4.2 ppm. The most likely structure is: 357
14 48. Predict the product(s) for the following reaction. 49. Rank the reactivity of the following dienes with maleic anhydride, starting with the fastest. A. IV > I > II > III B. III > IV > II > I C. III > II > I > IV D. IV > III > II > I 50. How many pi electrons are there in the following aromatic compound? A. 14 B. 16 C. 12 D
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