A. B. C. D. 2. Which compound does not give a stable Grignard reagent when reacting with Mg metal?

Transcription

1 Practice Test, Chemistry 2220 Final Exam 1. Which structure has the MST signals for its proton NMR? 2. Which compound does not give a stable Grignard reagent when reacting with Mg metal? 3. Which of these reaction sequences gives m-nitropropylbenzene from benzene? A. B. C. D.

2 4. Which compound has the following π orbital energy level diagram? 5. Which of the following compounds is insoluble in water and (aq), and soluble in Na(aq) and NaC 3 (aq)? 6. Which of the following structures is not involved in the aldol condensation of benzaldehyde and acetaldehyde with base catalyst? A. B. C. D.

3 7. Which mechanistic step is involved in a Grignard reaction? A. B. C. D. 8. Which of the following compounds has two singlets, 1.30 ppm (6 ) and 4.00 ppm (4 ) in its proton NMR spectrum, and three peaks in its 13 C NMR spectrum? C 3 C 3

4 9. Which structure is not a steroisomer of this sugar (ribulose) shown here? 10. What is the product of the following reaction sequence? 11. Which of the following is an intermediate involved in the reaction shown? C 6 5 C C 2 + A. C 6 5 CC 2 B. C 6 5 CC 2 C. C 6 5 CC 3 D. C 6 5 C 2 C 2

5 12. Which one is the major organic product expected from the following reaction? 13. What is the structure of the major organic product expected from the following reaction? N N C 3 + A. N N C 3 B. N N C 3 C. N N C 3 D. N N C 3

6 14. Which of the following pathways is the best for the synthesis of CC 3 from C 2 C 2 Br A. KMn LiCu(C 3 ) 2 Mg C 3 + B. -, heat 2 ether 2 K Br 2 2 NaN 2 gs 4 C. D. heat C 4 heat 2 S 4 2 Cr 4 C 3 MgBr ether 15. Which of the following is an intermediate in this reaction? 2 N 2 N A. 2 N Na reflux 2 N 2 N B. C. D. 16. What are the products of this reaction?

7 17. From the following information given for tyrosine, which of the following forms will be predominant in solution at a p 12? pka pka conj. acid 2 N C 2 C C pka N C 2 C C C 2 3 N C C 3 N C 2 C C 2 N C 2 C C 18. What is the product of the following reaction?

8 19. Which of the Following is a Zwitterion? C C N 3 3 N C 2 C C 1 3 N C 2 C C 2 3 N (C 2 ) 4 C C 3 2 N R C C 3 N R C C 4 5 A. 1 and 3 B. 4 only C. 5 only D. 2 only 20. Rank the following bases in order of decreasing strength (strongest base first) A. IV, III, II, I B. III, IV, I, II C. III, I, IV, II D. IV, II, III, I 21. What is the main organic product from the reaction of C 3 C= + Ph 3 P=C(C 3 ) 2? A. (C 3 ) 2 C B. C 3 C=C(C 3 ) 2 C. C 3 C=CC 3 D. C 3 C=CPh 22. A compound with the molecular formula C reacts with excess hydrogen and a catalyst to yield a compound with the formula C The compound could have: A. 2 rings and 2 double bonds B. 1 ring and 3 double bonds C. 3 rings and 1 double bond D. 0 rings and 4 double bonds

9 23. What is the major product of the following reaction 24. What would be a simple chemical test to distinguish between benzene and cyclohexene? A. Na in water B. Br 2 in C 4 C. AgN 3 in C 2 5 D. NaS 3 in water 25. Rank the reactivity order of the following dienes with maleic anhydride, starting with the slowest I II III IV A. IV<I<II<III B. III<IV<II<I C. III<II<I<IV D. IV<III<II<I 26. What is the IUPAC name for A. 4-bromo-1-phenyl-2-pentanone B. 2-bromo-5-phenyl-4-pentanone C. 4-bromo-1-benzyl-2-pentanone D. 2-bromo-5-benzyl-2-pentanone

10 27. What is the product of the following reaction? 28. The relative reactivity of acyl compounds towards nucleophilic substitution is A. Amide> ester> acid anhydride> acyl chloride B. Acyl chloride>ester> acid anhydride>amide C. Acyl chloride> acid anhydride>ester>amide D. Acid Anhydride>acyl chloride> ester> amide 29. What is the name of the following compound? A. Dimethylthioketone B. Dimethylsulfoxide C. Dimethylsulfone D. Dimethylsulfide S 30. The reaction that takes place here is called: N 2 1) NaC 3 (aq), heat N2 2) 3 + A. Electrophilic Aromatic Substitution B. Electrophilic Aromatic Addition C. Nucleophilic Aromatic Substitution D. Nucleophilic Phenolation

11 31. Arrange these dienes by stability, most stable first. A. I > II > III > IV B. II > I > III > IV C. IV > III > I > II D. IV > I > III > II 32. What is the major organic product of this reaction? 33. A pentapeptide has the following composition: Asp, Glu, is, Phe, Val. After partial hydrolysis, the fragments are: Val-Asp, Glu-is, Phe-Val, Asp-Glu. What is the sequence? A. is-glu-asp-val-phe B. Asp-Glu-is-Phe-Val C. Phe-Val-Asp-Glu-is D. Phe-Val-Glu-is-Asp 34. What class of sugars does the following molecule belong to? C C 2 A. L-Ketopentose B. D-Aldopentose C. L-Aldohexose D. D-Aldohexose

12 35. ow would you convert an unsaturated fatty acid into a saturated fatty acid? A. KMn 4, -, heat B. -, 2 heat; then 3 + C. 2, Ni, pressure D. 3 +, 2, heat 36. Which of the following pathways is the best for the synthesis of the following compound from benzene? Br A. Br 2 /FeBr 3, then K B. Br 2 /FeBr 3, then N 3 / 2 S 4, then NaN 2 /, then 2 /Pt then Cu 2 /Cu 2+ / 2 C. Br 2 /FeBr 3, then N 3 / 2 S 4, D. N 3 / 2 S 4, then N 3 / 2 S 4, then N 3 / 2 S 4, then 2 /Pt, then Br 2 /FeBr 3, then 2 /Pt, then NaN 2 /, then Cu 2 /Cu 2+ / 2 then NaN 2 /, then Cu 2 /Cu 2+ / Which compound reacts with 2 NC 3 and 2 /Pt to form C 3 C 2 C 2 C(C 3 )NC 3? A. C 3 C 2 C 2 C(C 3 ) B. C 3 C 2 C 2 CC 3 C. C 3 C 2 C 2 C 2 C 2 D. C 3 C 2 C 2 C 2 C 38. Which of these can be used to transform butanoic acid into 1-butanol? A. NaB 4 B. LiAl 4 C. PCC D. 2 Cr Which of these forms when 1,3-butadiene reacts with Br (no peroxides)? A. C 2 =C-C 2 -C 2 Br B. C 2 =C-CBr=C 2 C. C 3 -CBr=C-C 3 D. C 2 =C-CBr-C 3

13 40. Which is the major product of the following reaction? + A. B. C. D. 41. In the following derivative of guanine, what is the splitting pattern of the proton located at the position marked? A. singlet B. doublet C. triplet D. multiplet 42. Which of the following reagents would you use in order to synthesize 2-methyl-1- propanamine, using NaN 3 followed by reduction? A. tert-butyl bromide B. isobutyl bromide C. isopropyl bromide D. propyl bromide 43. Which functional group is not present in all peptides? A. Amine B. Aldehyde C. Carboxylic acid D. Amide 44. omit 45. omit

14 46. Which of these is an intermediate involved in the following reaction: Br 2 L i g ht B r Br A. B. C. D. 47. Which of the following is the strongest acid? A. Aniline B. Toluene C. Phenol D. Styrene 48. Which of these syntheses would yield butanoic acid from 1-propanol: A. Br Mg ether C B. PCC C. KMn 4 -, heat 3 + D. S 2 Mg ether 2 C What is the major product of the following reaction? Br NaCN LiAl 4 A. C B. N 2 C. N 2 D. CN 50. Which statement is correct for this sugar? A. This is a hemiacetal and a reducing sugar. B. This is an acetal and a reducing sugar. C. This is a hemiacetal and a non-reducing sugar D. This is an acetal and a non-reducing sugar