/120 /200. Last 4 digits of Banner No. Score. I. Multiple Choice ( /40) II /40 III /10 IV /10 V /20. Total score. Chem 2320 Final Exam.

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1 hem 2320 Final Exam April 30, 2007 Name: (First) (Last) (Please print) Last 4 digits of Banner No. Score I. Multiple hoice ( /40) /120 II /40 III /10 IV /10 V /20 Total score /200 1

2 I. Multiple choice questions. (3 points each). Please put your answers on Scantron sheet. Your score will be graded based only on your answers from Scantron sheet. 1. What is not the name for the following compound? 3 acetone dimethyl ketone 2-oxoketone propanone 2. What is the name for the following compound? benzylcarbonyl benzaldehyde phenylaldehyde phenylketone 3. What is the name for the following compound? 2,6-dimethylphenol 1,5-dimethylphenol 2,6-dimethylanisole 1,5-dimethylanisole 4. What is the name for the following compound? N 2 p-aminotoluene p-nitrotoluene p-nitrostyrene 3-aminostyrene 5. What is the name for the following compound? benzyl phenoate phenyl benzoate benzyl benzoate phenyl phenoate 2

3 6. What is the name for the following compound? (R)-3-hydroxybutanal (S)-3-hydroxybutanal (R)-3-hydroxybutanol (S)-3-hydroxybutanol 7. What is the name for the following compound? hexanediol hexanedial hexyldiol hexyldial 8. What is the name for the following compound? N (R)-2-cyanocyclopentanone (S)-2-cyanocyclopentanone (R)-2-nitrilecyclopentanone (S)-2-nitrilecyclopentanone 9. What is the name for the following compound? Br heptylol bromide heptaneacyl bromide heptanoyl bromide heptane bromide 10. Which of the following compounds undergo S N 1 reaction most rapidly? Br Br Br I II III I II III II and III have the same rate of reaction. 3

4 11. What could be the product for the following reaction? Br NaN 2 liquid N 3 N 2 N What is the expected product for the following reaction? l 2 (1 equiv.) Fel 3 l l l l l 13. What is the correct order of decreasing reactivity (fastest to slowest) toward the electrophilic aromatic substitution for the following compounds? 2 I II III IV 14. What could be the major product for the following reaction? III>II>IV>I II>I>IV>III I>II>III>IV IV>III>II>I Me l Zn (g) l, heating Major? All 3 Me Me Me Me 4

5 15. What could be the product for the following reaction? Mg, Et 2 D 2? Br D MgBr 16. What could be the product for the following reaction? N l, 2 heat? N N 2 N What could be the product for the following reaction? 2 2 P 2 5?

6 18. What could be the product for the following reaction? 1. MgBr (2 equiv.) 2. +, 2 product? 19. What could be the product for the following reaction? 1) Sl 2 2) 2 N 2 pyridine? N N 2 2 l none of the above 20. What could be the product for the following reaction? 1) P 2) 2, + removal of water none of the above 6

7 21. What could be the product for the following reaction? 1) Na 2 r 2 7, +, heat 2) 2, + removal of water none of the above 22. What could be the product for the following reaction? 1) Mn 2 2) MgBr 3) + / 2 none of the above 23. What could be the product for the following reaction? 1) (l) 2, Me 2 S=; Et 3 N 2) Ph 3 P 2 l none of the above 7

8 24. What could be the product for the following reaction? 2 N N 2 + removal of water? N N 2 N 2 N 2 N 2 N N 25. What could be the major product for the following reaction? N + removal of water Major? N N N N 26. What could be the product for the following reaction? + removal of water? 8

9 27. What could be the product for the following reaction? 3 l 2 (excess) -, 2 + l 3 l l 28. What could be the product for the following reaction? 1) Br 2, +, 2 2) S - S S S none of the above 29. What could be the product for the following reaction? 1) Br 2, +, 2 S 2) t-bu - K + S 3) S - 3 S none of the above 30. What could be the product for the following reaction? 1) Br 2, PBr 3 2) 2 Br Br Br Br 9

10 31. What could be the product for the following reaction? 1) pyrrolidine removal of water 2) 2 = (1 equiv.) 3) +, 2 pyrrolidine: N What could be the product for the following reaction? LDA add slowly +, What could be the product for the following reaction? 2 1) base 2) +, What could be the best base to be used for the first reaction in Q. 33? pyridine 10

11 35. What could be the product for the following reaction? 1) Na, N 3 2) s 4 then What could be the product for the following reaction? 1) 2, Lindlar's catalyst 2) Ph 3 3) +, Which of the following synthesis cannot provide benzoic acid as the final product? K 2 r Br All +, heat Br 2 3 FeBr 3 Mg, Et 2 1) 2 2) 3 + Mn 2 Ph 3 1) 3, -78 o 2) Me 2 S 11

12 38. What could be the product for the following reaction? + 1) - 2) +, 2 heat product What could be the product for the following reaction? Me Me 1) NaMe 2) l, 2 heating product + 2 Me 40. What could be the product for the following reaction? 1) s 4 then 2 2) I 4 ontinue to the next page 12

13 II. Use the provided table and fill in compound structures and reagents for the following synthesis. Make sure your answer is correctly put in the designated box of the given table. No partial point will be given for the misplaced answer. (40 points) XIII S 2 2 S 2 2 Raney Ni XIV Br 2 hν D Br - B 1. B , - P F - IV V VI Sl 2 (excess) 2 N (excess) r 3, + - I II A heat, + removal of water X E Br 2, 2, + VIII tert-bu - NaN IX - XII Ph 3 P 1.LiAl , 2 1. NaB , 2 XI VII III heat, + ontinue to the next page 13

14 A: B: : D: E: F: I: II: III: IV: V: VI: VII: VIII: IX: X: XI: XII: XIII: XIV: ontinue to the next page 14

15 III. Propose an electron-pushing mechanism for the following reaction. (10 points) ontinue to the next page 15

16 IV. Propose an electron-pushing mechanism for the following reaction. (10 points) 2 - ontinue to the next page 16

17 V. Propose a synthesis for ketoprofen, an anti-inflammatory drug from the provided starting materials. You can use any reagents, acids, or bases you have learned but you can only use the provided starting materials. (10 points) From 2 Br 3 2 ketoprofen 2 Br NaN 17

1. What is the name for the following compound? (a) (b) (c) p-methylphenol m-methylphenol 3-methylanisole. None of the above

1. What is the name for the following compound? (a) (b) (c) p-methylphenol m-methylphenol 3-methylanisole. None of the above hem 220 Final Exam May 2, 2005 Name: (first) (last) (Please print) Last 4 digits of I.D. I. Multiple hoice ( /0) Score /90 II /20 III /10 IV /10 V /10 Bonus /10 Total score /140 1 I. Multiple choice questions.