Chapter 5
1. What is the relationship between the following two compounds?
A. Constitutional isomers
B. Stereoisomers
C. Identical
D. Not isomers, different compounds entirely.
2. What is the relationship between the following two compounds?
A. Constitutional isomers
B. Stereoisomers
C. Identical
D. Not isomers, different compounds entirely.
3. What is the relationship between the following two compounds?
OH OH
A. Constitutional isomers
B. Stereoisomers
C. Identical
D. Not isomers, different compounds entirely.
4. What is the relationship between the following two compounds?
A. Constitutional isomers
B. Stereoisomers
C. Identical
D. Not isomers, different compounds entirely.
5. What is the relationship between the following two compounds?
A. Constitutional isomers
B. Stereoisomers
C. Identical
D. Not isomers, different compounds entirely.
6. What is the relationship between the following two compounds?
OH
O
A. Constitutional isomers
B. Stereoisomers
C. Identical
D. Not isomers, different compounds entirely.
7. Is the following alkene cis, trans, or neither?
OMe
8. Is the following alkene cis, trans, or neither?
F
F
9. Is the following alkene cis, trans, or neither?
10. Is the following alkene cis, trans, or neither?
11. Is the following alkene cis, trans, or neither?
O
O
12. Is the following internal alkene cis, trans, or neither?
HO
13. Draw all the isomers of a hydrocarbon with molecular formula C4H8.
14. Draw all the isomers of a hydrocarbon with molecular formula C4H6.
15. Locate the chiral centers in the following compound.
O
OH
O
16. Locate the chiral centers in the following compound.
N
17. Locate the chiral centers in the following compound.
OH
O
O
HO
18. Locate the chiral centers in the following compound.
O
HO
HO
OH
OH
OH
19. Locate the chiral centers in the following compound.
OH
NH2
20. Identify the relationship between the following two structures.
OH
OH
A. Enantiomers
B. Identical
C. Neither
21. Identify the relationship between the following two structures.
OH OH
A. Enantiomers
B. Identical
C. Neither
22. Identify the relationship between the following two structures.
OH OH
A. Enantiomers
B. Identical
C. Neither
23. Identify the relationship between the following two structures.
OH OH
A. Enantiomers
B. Identical
C. Neither
24. Identify the relationship between the following two structures.
OH OH
A. Enantiomers
B. Identical
C. Neither
25. Draw the enantiomer of the following compound.
H
H
26. Draw the enantiomer of the following compound.
N
27. Draw the enantiomer of the following compound.
OH
NH2
28. Draw the enantiomer of the following compound.
O
HO
HO
OH
OH
OH
29. Draw the enantiomer of the following compound.
OH
O
O
HO
30. Assign the chiral center as R or S.
N
N
31. Assign the chiral center as R or S.
OH
O
O
HO
32. Assign the chiral center as R or S.
OH
33. Assign the chiral center as R or S.
OH
34. Assign the chiral center as R or S.
OH
35. Assign the chiral center as R or S.
OH
36. Provide an IUPAC name for the following compound.
OH
37. Provide an IUPAC name for the following compound.
OH
38. Which of the following is the correct structure for a compound with the IUPAC
name (R)-2-pentanol.
OH
OH OH OH
A. B. C. D.
39. Which of the following is the correct structure for a compound with the IUPAC
name (S)-3-methylheptane.
A. B. C. D.
40. Draw the structure for a compound with the IUPAC name (S)-3-methylheptane.
41. Draw the structure for a compound with the IUPAC name (R)-4-ethyloctane.
42. Which of the following is the correct IUPAC name for the following structure?
A. (S)-3-ethyl-2-methylhexane
B. (R)-3-ethyl-2-methylhexane
C. (S)-3-ethyl-2-methylpentane
D. (R)-3-ethyl-2-methylpentane
43. Which of the following is the correct IUPAC name for the following structure?
A. (S)-2-ethylhexane
B. (S)-3-methylheptane
C. (R)-2-ethylhexane
D. (R)-3-methylheptane
44. Rank the following from highest to lowest priority.
A. -F B. -H C. –OH D. –SH
45. Rank the following from highest to lowest priority.
A. –CH3 B. –CN C. –CH2OH D. –Br
46. Rank the following from highest to lowest priority.
A. –CH2CH3 B. -CHCH2 C. –CCH D. –CH3
47. What is the %ee of a sample of carvone that exhibits a specific rotation of 20
(given that the specific rotation of R-carvone is -61)?
48. What is the %ee of a sample of carvone that exhibits a specific rotation of -40
(given that the specific rotation of R-carvone is -61)?
49. If a sample of carvone gives a specific rotation of -60 and the specific rotation of
R-carvone is -61, is the unknown sample R or S?
50. If a sample of carvone gives a specific rotation of 0 and the specific rotation of
pure R-carvone is -61, which enantiomer is the unknown sample?
51. What is the specific rotation of pure carvone if a sample of carvone of 85%ee has
a specific rotation of -54?
52. What is the specific rotation of pure S-carvone if a sample of R-carvone of 85%ee
has a specific rotation of -54?
A. -61
B. 64
C. 0
D. 61
53. What is the specific rotation of a sample of carvone that is an equal mixture of the
R and S enantiomers (R- carvone has a specific rotation of -61)?
A. -61
B. 64
C. 0
D. 61
54. What is the % of the R enantiomer in a sample of carvone that has a specific
rotation of 30, given that the specific rotation of R-carvone is -61?
A. 25.5%
B. 51%
C. 49%
D. 74.5%
55. What is the % of the R enantiomer in a sample of carvone that has a specific
rotation of -30, given that the specific rotation of R-carvone is -61?
56. What is the % of the S enantiomer in a sample of carvone that has a specific
rotation of 30, given that the specific rotation of R-carvone is -61?
A. 25.5%
B. 51%
C. 49%
D. 74.5%
57. What is the % of the R enantiomer in a sample of carvone that has a specific
rotation of -20, given that the specific rotation of R-carvone is -61?
A. 33%
B. 66.5%
C. 33.5%
D. 67%