Exam 2 Chem 109a Fall 2004
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1 Exam 2 Chem 109a Fall 2004 Please put your name and perm number on both the exam and the scantron sheet. Next, answer the following 34 multiple-choice questions on the scantron sheet. Then choose one A-type mechanism question and one B-type mechanism and give your two mechanism on the space provided below the question. We will only grade one of each. 1. What would be the major organic product of the following reaction? Page 1
2 2. What would be the major organic product of the following reaction? Page 2
3 3. What would be the expected product of the following reaction? 4. What reagent(s) would accomplish the following reaction? Br 2 NBS Br 2 + light Br 2 + FeBr 3 HBr Page 3
4 5. Which reagents would you expect to accomplish the following transformation? BH 3 then H 2 O 2, - OH Hg(O 2 CCH 3 ) 2, H 2 O then NaBH 4 H 2 O, H + KMnO 4, H 2 O, cold cat. OsO 4, H 2 O 2 6. Predict the product of the following reaction: Equal amounts of A and B Page 4
5 7. What would be the name of the following compound? 2,3-dimethylcyclopentene 1,5-dimethylcyclopentene cis-2,3-dimethylcyclopentene cis-1,5-dimethylcyclopentene trans-2,3-dimethylcyclopentene 8. Under special reaction conditions, α-pinene and β-pinene can be in equilibrium (caused to interconvert reversably). Using your knowledge of alkene stability, which of the following would be true at equilibrium? The α-isomer will predominate. The β-isomer will predominate. The isomers would be equally favored. A third isomer would predominate. None of these is true. Page 5
6 9. Predict the product of the following reaction: 10. What reagent would give the highest yield of the product shown below? K +- OtBu NaCN CH 3 S - Na + NaOH CH 3 O - Na + Page 6
7 11. Based on what you know about carbon-carbon double bonds, which of the following would be true of the allene shown? The two rings would be in the same plane. The two rings would be in perpendicular planes. There is no way to tell what geometric relationship the rings would have. The three carbons shown would not be co-linear. Allenes cannot exist. 12. What product would you expect from the reaction shown below? Page 7
8 13. What would be the MAJOR organic product of the following reaction? 14. How many chiral centers are present in β-cadinene? none What would be the complete name of the following? A. (2R,4S)-2-bromopentane (R)-2-bromo-4-methylpentane (S)-4-bromo-2-methylpentane (2R,4R)-2-bromo-4-methylpentane (S)-2-bromo-4-methylpentane Page 8
9 16. Which of the following statements is not true? Enantiomers have identical properties except in chiral environments or with plane-polarized light. Reactions involving only achiral or racemic materials must produce achiral or racemic products. Diastereomers have identical properties in all environments. Enantiomers exhibit equal and opposite optical rotations. All of the above are true. 17. The relationship between the following two compounds is: same molecule enantiomers diastereomers mesos conformers 18. A particular reaction produces the following two alcohols in a ratio of 95 : 5. The enantiomeric excess (% ee) is: none of these Page 9
10 19. Which of the following molecules is not chiral? Page 10
11 20. What is the correct structure for (R)- 4-methyl-2-heptanone? 21. Which of the following is NOT TRUE for a meso compound: It is achiral It will rotate plane polarized light It may be cyclic or acyclic It is a stereoisomer It has a mirror plane Page 11
12 22. The structure of (-)-geosmin is shown below. Which structure would be that of its enantiomer, (+)-geosmin? None of these. 23. What technique(s) can be used to obtain non-racemic compounds from racemic material? Resolution Distillation Extraction Column chromatography Both B and C Page 12
13 24. What would be the major product of the following reaction? Page 13
14 25. What reactants are required to achieve the following transformation? 26. To which side (if any) would the following equilibrium lie? to the left to the right equally to the right and left there is no way to tell only S N 2, S N 1 and E2 reactions are possible 27. Which of the following reagents would best accomplish a typical S N 2 reaction? CH 3 OH H 2 O HCN KCN KO t Bu Page 14
15 28. Which of the following is the best leaving group? Page 15
16 29. Predict the major product of the following reaction: No reaction will occur. Page 16
17 30. What would be the major organic product of the following reaction? 31. Which would be true of the following reactions? cis would react faster trans would react faster cis and trans would react at the same rates no reaction is expected under these conditions the product shown would not be formed Page 17
18 32. What would be the major product of the following reaction? Page 18
19 33. Predict the MAJOR product of the following S N 1 reaction: 34. What is the major product of the following reaction: Page 19
20 Answer Key - Ferret:Users:thomaspe:Documents:classes:chem109a:Test2. ef 1. C 2. B 3. B 4. A 5. B 6. E 7. A 8. A 9. D 10. A 11. B 12. C 13. B 14. D 15. B 16. C 17. C 18. C 19. D 20. E 21. B 22. C 23. A 24. C 25. E 26. A 27. D 28. A 29. D 30. D 31. A 32. A 33. E 34. E Page 20
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