/12 /20 /16 /16 /12 /12 /16 /16 /10 /5 /5 /10 /150

Transcription

1 ``hem Final Exam May 3, 2002 Name: (first) (last) (Please Print) Page Total score Score /12 /20 /16 /16 /12 /12 /16 /16 /10 /5 /5 /10 /150 1

2 I. Multiple choice questions (30 questions, 4 points each). Write down your answer in the provided space in front of every question. There is no partial point if your marked (circled) answer is different from what you write down. Answer Q.1 and Q.2 according to the following reaction I II III IV V VI ( ) 1. Which product(s) can be obtained from S N 2 reaction? I, III II, III I II ( ) 2. Which product(s) can be obtained from E1 reaction? IV, V, VI IV, V V, VI I, II, III ( ) 3. What is the order of decreasing rate in an E2 elimination for the following compounds? I: II: III: I>II>III II>I>III I>III>II III>I>II 2

3 ( ) 4. What is the name for the following compound? 3 p-methylphenol m-dimethylphenol o-methylanisole 3-methylanisole ( ) 5. What is the name for the following compound? N 2 2 p-aminotoluene m-nitrotoluene m-nitrostyrene 3-aminostyrene ( ) 6. What is the name for the following compound? acetic benzoic anhydride acetic phenoic anhydride acetic benzoic ester acetic phenoic ester ( ) 7. What is the name for the following compound? 2 5 N trans-n-ethyl-3-pentenamide trans-1-ethyl-3-pentenamide trans-n-ethyl-4-pentenamide trans-1-ethyl-4-pentenamide ( ) 8. What is the name for the following compound? 3 2 N 2 2 (R)-3-methylhexaneamine (S)-3-methylhexaneamine (R)-3-methylhexanenitrile (S)-3-methylhexanenitrile 3

4 Select the correct product for the following reactions from Q.9 to Q.30 ( ) 9. 1) P 2) 2, ( ) 10. 1) Na 2 r 2 7, +, heat 2) 2, ( ) ) l, All 3 2) NaB ( ) 12. 1), Fel 3 2) Na 2 r 2 7, heat 2 2 4

5 ( ) 13. 1) Mg, Et 2 2) D 2 2 D D D ( ) 14. 1) Pl 3 2) l ( ) ) heat, removal of 2 2) excess N 3, 25 o N 2 N 2 N 2 N 2 N ( ) 16. 1) Mn 2 2) ( ) 2 uli 5

6 ( ) 17. 1) NaN 2) +, 2, hea t 2 N N 2 N 2 ( ) 18. 1) (l) 2, Me 2 S; E t 3 N 2) Ph 3 P 2 l ( ) 19. 1) 2, Lindlar's catalyst 2) 3, then

7 ( ) ) Et Et P 2) (i-bu) 2 Al (DIBAL), -78 o, then ( ) ) 3, then 2 2 2) P 3 3) 2 N, pyridine 4) LiAl 4 N N ( ) 22. 1) 2, Fel 3 2) ( 2 =) 2 uli 3) s 4 7

8 ( ) 23. 1) 2, Fel 3 2) ( 2 =) 2 uli 3) R 3 3 ( ) 24. 1) l 2, All 3 2) Mg, Et 2 3) the n 2 4) Pl 3, pyridine 2 l ( ) 25. 1) l 2, All 3 2) Mg, Et 2 3) then 2 4) Sl 2, pyridine l ( ) ) NBS, heat 2) tert-bu 3) 3, then Me 2 S 4) Et 2 N, NaB 3 N NEt 2 NEt 2 8

9 ( ) 27. 1) 2, Lindlar's catalyst 2) s 4, I 4 3) Zn (g), l, heat 2 ( ) 28. 1) 3, then NaB 4 2) S 2 l (Msl), pyridine 2 3) Na, heat ( ) ) 3, then NaB 4 2) Pl 3 3) NaN, heat 4) +, 2, heat N N 2 ( ) 30. 1) 2, Pt/ 2) Na 2 r 2 7, heat 3) Sl 2 4) 2 N 2 N N 9

10 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. (10 points) N S 4 Pd/ S 3 2 S 4 N A I II III IV Pl 3 (2 equivalences) K 2 3 S 3 1) +, 2, heat 2) - N 3 VII N 2 B VI V VIII S 3 N 2 1) +, 2, heat 2) - (azo compound) S N 2 Fill in your answers for part II in the following table. A: B: I: II: III: IV: V: VI: VII: VIII: 10

11 III. Propose an electron pushing mechanism for each of the following reactions. (5 points each) NN 2 K, 2 heat 3 2 ontinue to the next page 11

12 2. 3 cat. 2 S 4 ontinue to the next page 12

13 IV. Propose a synthesis for novocain using the provided starting material and any reagents you know: (10 points) starting material 2 2 N from 2 2 N 2 Novocain N 2 13