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

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1 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

2 I. Multiple choice questions. ( 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 the name for the following compound? p-methylphenol m-methylphenol o-methylanisole -methylanisole 2. What is the name for the following compound? N 2 2 p-aminotoluene m-nitrotoluene m-nitrostyrene -aminostyrene. What could be the product for the following reaction? 1) P 2) 2, + removal of water What could be the product for the following reaction? 1) Na 2 r 2 7, +, heat 2) 2, + removal of water

3 5. What could be the product for the following reaction? 2 N 1) l, All 2) LiAl 4 ) + / 2 2 N 2 N 2 N 6. What could be the product for the following reaction? 1) Br, Na 2) l, All What could be the product for the following reaction? 1) EtMgBr (1 equivalents) 2) l, 2 product 8. What could be the product for the following reaction? 1) Mn 2 2) MgBr ) + / 2

4 9. What could be the product for the following reaction? 1) l 2, All 2) Mg, Et 2 ) then 2 4) K 2 r 2 7, + room temp 10. What could be the product for the following reaction? 2 1) NBS, heat 2) tert-bu ), then Me 2 S 4) 2 N 2, NaB N N 2 Br N 2 Answer Q.11 to Q.1 according to the following synthetic scheme: 1) l, All 2) 2 I A N + II 11. What could be the structure of compound I? 2 4

5 12. What could be the structure of compound II? 2 N 2 N 1. What could be the structure of reagent A? KMn 4, heat then 2 2 s 4, KI 4 Ph 14. What could be the product for the following reaction? 1) 2, Pt/ 2) Na 2 r 2 7, heat ) Sl 2 4) 2 N, Et N 2 N N 15. What could be the product for the following reaction? 1) Br 2, PBr 2) 2 Br Br Br Br 5

6 16. What could be the product for the following reaction? + 1) - 2) +, 2 product 17. What could be the product for the following reaction? + 1) - 2) +, Which of the following compounds are aromatic? N N N N N N I II III IV V N N N VI VII VIII IX X I, II, III, IV, V, VI, VIII, IX, X I, II, IV, V, VI, VII, IX I, II, III, IV, V, VI, VII, X I, II, IV, V, VI, VII, VIII 19. Which one of the reagents could be used for the following transformation? 2 reagent then NaB 4 s 4 then I 4 then 2 2 KMn 4, heating 6

7 20. What could be the product for the following reaction? 1) 2, Lindlar's catalyst 2) s 4 then What could be the product for the following reaction? 1) Na, N 2) Ph ) +, What is the correct order of decreasing acidity (strongest to weakest) for the protons indicated by arrow in the following compounds? I II III IV l V VI V>IV>III>II>I>VI V>II>III>IV>I>VI V>IV>I>III>II>VI V>III>I>IV>II>VI 7

8 2. What could be the major product for the following reaction? F N 2 S 4 Fe, l then Na F F F F 2 N 2 N N 2 N 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 I>II>III>IV II>I>IV>III III>II>IV>I IV>III>II>I 25. What could be the product for the following reaction? K 2 r S 4 heat What is the name for the following compound? benzaldehyde benzylcarbonyl phenylaldehyde phenylketone 8

9 27. What's the name for the following compound? N 2 Toluene Styrene Aniline Anisole Answer Q.28 to Q.0 according to the following synthetic scheme: A + removal of water 1. B 2. +, What could be reagent A? What could be reagent B? 2, Pt/ LiAl 4 then +, 2 MgBr (2 equivalents) R 0. What could be reagent? Ph P 2 s 4, KI 4 then Zn S 2 2 S then Raney Nickel 9

10 II. Use the provided table (next page) 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. (20 points) V B ( ) 2 S A I II PBr (excess) (excess) N 2 (excess) - III IV heat, + 2 D E 10

11 A: B: : D: E: I: II: III: IV: V: ontinue to the next page 11

12 III. Propose an electron-pushing mechanism for each of the following reactions. Briefly explain why the hydrolysis of ester in acidic condition is reversible (reaction a) while in basic condition (reaction b) is irreversible. (10 points) ontinue to the next page 12

13 IV. Propose an electron pushing mechanism for reaction 1 only. For the following two laisen condensations, briefly explain why the yield for reaction 1 could be much better than that of reaction 2 (10 points) 2 - (reaction 1) 2 - (reaction 2) ontinue to the next page 1

14 V. Propose a synthesis for the following compound (Isoamyl methoxycinnamate) 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 Isoamyl methoxycinnamate (new sunscreen waiting for FDA approval) Br 2 2 ontinue to the next page 14

15 VI. Bonus Points: propose a correct structure based on the following spectroscopic information (next two pages). Put all your analysis and answer on this page (page 15). The grading will base only on your analysis and answer of this page. (10 points) 15