/60 /100. Last 4 digits of Banner No. Score. I. Multiple Choice ( /20) II /20 III /10 IV /10. Total score. Chem 2320 Exam 3. March 26, 2007.

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1 hem 2320 Exam 3 March 26, 2007 ame: (first) (last) (Please print) Last 4 digits of Banner o. Score I. Multiple hoice ( /20) /60 II /20 III /10 IV /10 Total score /100 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 the name for the following compound? l cyclopentylcarbonyl chloride cyclopentanecarbonyl chloride cyclopentylacyl chloride cyclopentaneacyl chloride one of the above 2. What is the name for the following compound? benzyl chloride benzoyl chloride l benzene chloride phenyl chloride one of the above 3. What is the name for the following compound? Br 3 methyl 3-bromobutanoate methyl 4-bromobutanoate 4-bromopentanoate 5-bromopentanoate one of the above 4. What is the name for the following compound? anti-2-methylcyclohexanecarbaldehyde trans-2-methylcyclohexylcarbaldehyde trans-2- methylcyclohexylcarbonyl aldehyde trans-2-methylcyclohexanecarbaldehyde one of the above 2

3 5. What is the name for the following compound? l 2 3 ethyl (2S,5S)-2-chloro-5-formylhexanoate ethyl (2,5S)-2-chloro-5-carbonylhexanoate ethyl (2R,5S)-2-chloro-5-oxolhexanoate ethyl (2R,5S)-2-chloro-5-formylhexanoate one of the above 6. What is the name for the following compound? 2 3 ethyl 5-oxopentanoate ethyl 6-oxopentanoate ethyl 5-oxohexanoate ethyl 6-oxohexanoate one of the above 7. What is the name for the following compound? -ethyl--methylacetamide -isoproplacetamide -ethyl--methylpropanmide -ethyl--methylethylamide one of the above 8. What is the structure of 2,4-hexanedione? none of the above 3

4 9. What could be the product for the following reaction? 1. 3 MgBr 2. +, 2 product? one of the above 10. What is the order of increasing boiling points (from the lowest to highest) for the following compounds? I 2 II l III I, II, III II, III, I I, III, II III, I, II one of the above 11. What could be the reagent and reaction condition for the following transformation? 3? ethanol, a ethanol, + methanol, a methanol, + one of the above 4

5 12. What should be the product from the following reaction? 1) ab 4 2) +, removal of water product none of the above 13. What could be the product for the following transformation? 3 1) 3 2 MgBr (2 equivalents) 2) l, 2 product? none of the above 14. What should be the product from the following reaction? 3 1) a 2) +, 2, heat Product none of the above 5

6 15. What could be the product for the following reaction? 1) PBr 3 2) 3 2 Product none of the above 16. What could be the products for the following reaction? , removal of water Products I II III IV I, II I, II, IV III, IV II, III one of the above 17. What could be the product for the following reaction? 6

7 Br 1) 2) +, 2, heat product? 3 I II III IV V I II III IV V 18. What could be the product for the following reaction? , removal of water Product? I II III IV I II III IV one of the above 7

8 19. What could be the reagent for the following reaction? 1) reagent 3 MgBr 2) +, 2 Ph 3 P 2 ( 3 ) 2 uli 3 Br 3 none of the above Ph = What could be the reagent for the following reaction? 3 Et Et P 3 Product none of the above 3 ontinue to the ext page 8

9 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. o partial point will be given for the misplaced answer. (20 points) I 2 Raney i II + removal of water S A 3 S + removal of water III 1. LiAl , 2 ( 6 5 ) 3 P 2 IV 3 2 B l 3 2 V (2 equiv.) VII VI l 9

10 I: II: III: IV: V: VI: VII: A: B: : ontinue to the ext page 10

11 III. Show how ibuprofen can be prepared from benzene. You can use any reactants with four or less carbons. (10 points) multiple steps ibuprofen 3 ontinue to the ext page 11

12 IV. 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)