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Chapter 8
1. How substituted is the following alkene?
2. How substituted is the following alkene?
3. How substituted is the following alkene?
4. Provide an IUPAC name for the following compound.
5. Provide an IUPAC name for the following compound.
6. Provide an IUPAC name for the following compound.
7. Which of the following is the correct IUPAC name for the following compound?
A. 1-methyl-2-cyclohexene
B. 2-methylcyclohexene
C. 3-methylcyclohexene
D. 1-methyl-5-cyclohexene
8. Which of the following is the correct IUPAC name for the following compound?
A. 2-ethyl-1,1,3-trimethylbutene
B. 3-ethyl-2,4-dimethyl-2-pentene
C. 2,4-dimethylhexene
D. 4-ethyl-1,3-dimethyl-3-pentene
9. Which of the following is the correct structure of 4-methylcyclopentene.
A. B. C. D.
10. Which of the following is the correct structure of 2-methyl-1-butene?
A. B. C. D.
11. Draw the structure of 3-methylcyclopentene.
12. Draw the structure of 2,3-dimethyl-1-pentene.
13. Provide an IUPAC name for the following compound.
14. Is the following alkene E, Z, or neither?
15. Is the following alkene E, Z, or neither?
HO OH
16. Is the following alkene E, Z, or neither?
Cl
OH
17. Is the following alkene E, Z, or neither?
O
HO
18. Draw the E isomer of 2-methyl-3-heptene.
19. Draw the E isomer of 3,4-dimethyl-3-hexene.
20. Draw the Z isomer of 3,4-dimethyl-3-hexene.
21. Rank the following from most to least stable.
A. B. C. D.
22. Rank the following from most to least stable.
A. B. C.
A. A, B, C
B. C, B, A
C. B, C, A
D. B, A, C
23. Which of the following alkenes is more stable?
A. B.
24. Given the following alkane, draw the least stable alkene isomer with the same
basic skeleton.
25. Rank the following from most to least stable.
OH OH OH
A. B. C.
26. Show the mechanism for the following elimination, assuming that it is a concerted
reaction.
Br OMe
27. Show the mechanism for the following elimination, assuming that it is a concerted
reaction.
Cl
OMe
Ans:
28. Show the mechanism for the following elimination, assuming that it is a concerted
reaction.
I
OMe
29. Show the mechanism for the following elimination, assuming that it is a stepwise
reaction.
Cl
OMe
30. Show the mechanism for the following elimination, assuming that it is a stepwise
reaction.
Br OMe
31. Which of the following shows a mechanism for a concerted elimination.
A.
B.
C. D.
Br OMe
H
H
OMe
H
OMe
Br
H
OMe OMe
32. Which of the following shows the first step for a stepwise elimination.
A.
B.
C. D.
Br OMe
H
H
OMe
H
OMe
Br
H
OMe OMe
33. Which of the following is the most reactive in an E2 reaction?
Br Br Br
C.B.
A.
34. Which of the following is the most reactive in an E2 reaction?
Br
Br
Br
A. B. C.
35. Which of the following is the major product of the following reaction?
Cl
OMe
A. B. C.
36. Which of the following is the major product of the following reaction?
Cl
O
A. B. C.
37. Draw the major product of the following reaction.
Cl
O
38. What would be the best base for performing the following elimination?
Br
39. Which of the following would be the best base for performing the following
elimination?
A. B. C. D.
Br
NaOH NaOMe KOtBu H2O
40. What is the product of the following elimination?
41. What is the product of the following elimination?
Ph
OMe
Cl
42. What is the product of the following elimination?
Br
OMe
43. Which of the following alkyl halides would afford the indicated product upon
reaction with sodium ethoxide?
Ph
Ph
Cl
Ph
Cl
Ph
Cl
Ph
Cl
A. B. C. D.
44. Which of the following alkyl halides would afford the indicated product upon
reaction with sodium ethoxide?
Cl Cl Cl
Cl
A. B. C. D.
45. Which of the following alkyl halides would be more reactive in an E2
elimination?
Cl Cl
A. B.
46. Draw the isomer of 2-bromo-1,1,3-trimethylcyclohexane that would be more
reactive in an E2 elimination.
47. Draw the major product of the following reaction.
Br
OMe
48. Draw the major product of the following reaction.
Br O
49. Draw the major product of the following reaction.
Cl
OMe
50. Draw the major product of the following reaction.
Cl
OMe
51. Draw the major product of the following elimination.
Br
NaOEt
52. Draw the major product of the following reaction.
Br
OMe
53. Draw the major product of the following reaction.
Br O
54. Draw the major product of the following reaction.
Br
OMe
55. Draw the major product of the following reaction.
Br
O
56. Draw the major product of the following reaction.
OMe
57. Draw the major product of the following reaction.
I
O
58. Which of the following is most reactive in an E1 reaction?
Br Br Br
C.B.
A.
59. Which of the following is most reactive in an E1 reaction?
Br
Br
Br
A. B. C.
