CHEM 241 (Davis) Organic Chemistry II Final Exam Friday December 14, NAME (Last, First) DISCUSSION SECTION #
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1 CEM 241 (Davis) rganic Chemistry II Final Exam Friday December 14, NAME (Last, First) DISCUSSIN SECTIN # Initial of last name Instructions Please fill in your name in the space above and on the next page Please put your discussion section number in the space provided. Please print the initial of your last name in the box above Please sign your name under the onor Code acknowledgment on next page
2 2 Name CEM 241 Final Exam 14 December, 2007 University onor Code Acknowledgment I have neither given nor received assistance during this exam. Your Signature Part 1 (100) Part 2 (40) Part 3 (60) Total Points (out of 200)
3 PART 1-Multiple choice with 20 questions at 5 points each (100 pts) Circle the best value for the pka of methanol (C3) Circle the best value for the pka of acetone (C3CC3) Circle the best value for the following equilibrium constant. _ Keq + + _ Circle the number of different types of hydrogen atoms in the following compound. 3 C C Circle the strongest base. _ N N N
4 6. Circle the compound that is the best Lewis acid. PAGE 2 4 C N C N B 7. Circle the best value for the strength of a hydrogen bond X-... Y (kcal/mol) 8. Circle the best value for the strength of a C-C single bond (kcal/mol) 9. Circle the compound that is reduced slowest by LiAl 4. S 10. Circle the most reactive carbocation. C 3 C 3 F 3 C C 3 C 3 F 3 C + CF 3 3 C + C 3 + C 3 3 C + C Circle the compound that reacts fastest with Br 2. N NMe 2 3 C C 3 3 C C 3 3 C C 3 3 C C 3
5 12. Circle the compound that reacts fastest with NaB C 3 C 3 C C 3 N Circle the compound that can form the most hydrogen bonds with water. 2 N 3 C C 3 C 3 C Circle the conformation that can react with base to give an epoxide. Br C 3 C 3 Br C 3 C 3 Br 3 C C 3 Br C 3 C Circle the name of the author of our rganic chemistry text. Breeze Bobwhite Bruice Biochem Baltic 16. Circle the most acidic in the following compound. 3 C C Circle the least electrophilic carbonyl in the compound below. 2 N
6 6 18. Circle the compound with the most acidic hydrogen 19. Circle the compound that has the highest enol content. 20. If exactly one equivalent of - is added to the cyclobutane 1, a mono-carboxylic acid is formed. Draw the structure of the expected hydrolysis product. Me N 2 - TF 1
7 7 Part 2-Short Answer 21. Reaction of ethanol with 2Cr4 in 2 gives acetic acid while reaction of ethanol with pyridinium chlorochromate (PCC) in C22 gives acetaldehyde. Both 2Cr4 and PCC are Cr (VI) oxidants. early explain why the product obtained upon oxidation of ethanol by Cr (VI) is so dependant on the solvent. (10 pts) 2 Cr 4 2 PCC C 2 2
8 8 22. As shown below, CN reacts with an α,β-unsaturated aldehyde to give primarily the 1,4- conjugate addition product, rather than the 1,2-addition product. + -C N NC + NC 1,4-addition major product 1,2-addition minor product Briefly explain, then, why reaction of CN and benzaldehyde gives only cyanohydrin (the 1,2-addition product) and none of the 1,4-addition product aldehyde (10 pts). + -C N + CN 1,2-addition nly product CN No 1,4-addition product observed
9 9 23.The acid-catalyzed hydrolysis of the following 2 acetals occurs at much different rates. Draw structures of reaction intermediates and provide a brief explanation to illustrate why these 2 acetals undergo hydrolysis at such different rates (10 pts). + 2 p-ts TF Reaction is complete in 1 hour at 20 o C + 2 p-ts TF Reaction is complete in 24 hours at 60 o C
10 Treatment of the 2 compounds with Ag + gives the respective benzyl cations. Circle the more stable benzyl cation. Use resonance forms to illustrate and justify your answer. (10 pts) + + Ag + Ag + Me Me Me + Ag + Ag + + Me
11 Part 3. Mechanism with 2 questions at 20 points each (60 pts) Provide a stepwise mechanism for the following reaction: + S + S 2 +
12 26. Provide a stepwise mechanism for the following reaction: 12 C 3 N + 3 C Al 3 + N C 3 C 3 C 3
13 27. Show a step-wise mechanism for the following base-catalyzed rearrangement: 13-2
14 BLANK PAGE FR SCRATC WRK 14
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