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Chapter 4
1. What is the parent chain for the following compound?
A. octane
B. hexane
C. heptane
D. decane
2. What is the parent chain for the following compound?
3. What is the parent chain for the following compound?
4. What is the IUPAC name for the following compound?
A. 3-isopropyl-5-ethylheptane
B. 2-methyl-3-ethyl-5-ethylheptane
C. 3,5-diethyl-2-methylheptane
D. 2-methyl-3,5-diethylheptane
5. What is the IUPAC name for the following compound?
A. 2,5-diethylhexane
B. 3,6-dimethyloctane
C. 2-ethyl-5-methylheptane
D. 2,5-dimethylheptane
6. What is the IUPAC name for the following compound?
A. 2,3,5-triethylhexane
B. 2,4,5-triethylhexane
C. 2,4-diethyl-5-methylheptane
D. 4-ethyl-3,6-dimethyloctane
7. What is the IUPAC name for the following compound?
A. 1-ethyl-2-methylcyclohexane
B. 2-ethyl-1-methylcyclohexane
C. 1-ethyl-2-methylhexane
D. cyclononane
8. What is the IUPAC name for the following compound?
9. What is the IUPAC name for the following compound?
10. What is the IUPAC name for the following compound?
11. What is the structure of an isopropyl group?
12. What is the common name of the following substituent?
A. isopropyl
B. tert-butyl
C. iso-butyl
D. sec-butyl
13. What is the structure of [2.2.2]bicyclooctane?
14. Which of the following is an isopropyl group?
A. B. C. D.
15. What is the structure of 3-ethyl-2,4,6-trimethyloctane?
16. What is the structure of 3-ethyl-2-methylpentane?
17. What is the structure of 1-cyclopropyl-3-methylcyclopentane?
18. What are the structure and IUPAC names of all of the constitutional isomers of
C6H14?
19. Which of the following compounds are constitutional isomers?
A. B. C. D.
20. Which of the following compounds are constitutional isomers?
A. B. C. D.
21. Which of the following compounds are constitutional isomers?
A. B. C. D.
22. What is the relationship between the following two compounds?
A. Constitutional Isomers
B. The same compound
C. Completely different and not constitutional isomers
23. What is the relationship between the following two compounds?
A. Constitutional Isomers
B. The same compound
C. Completely different and not constitutional isomers
24. What is the relationship between the following two compounds?
A. Constitutional Isomers
B. The same compound
C. Completely different and not constitutional isomers
25. What is the relationship between the following two compounds?
A. Constitutional Isomers
B. The same compound
C. Completely different and not constitutional isomers
26. What is the relationship between the following two compounds?
A. Constitutional Isomers
B. The same compound
C. Completely different and not constitutional isomers
27. What is the correct stoichiometry of oxygen for the balanced oxidation reaction?
+__ O25 CO2+6 H2O
28. What is the correct stoichiometry of oxygen for the balanced oxidation reaction?
+__ O26 CO2+7 H2O
29. Complete the following combustion reaction, assuming that only CO2 and H2O
are formed.
+__ O2__ CO2+__ H2O
30. Complete the following combustion reaction, assuming that only CO2 and H2O
are formed.
+__ O2__ CO2+__ H2O
31. Draw a Newman projection for the following compound as viewed down the
indicated bond.
Cl
Br
32. Draw a Newman projection for the following compound as viewed down the
indicated bond.
Br
33. Draw a Newman projection for the following compound as viewed down the
indicated bond.
Cl
34. Which of the following is a Newman projection for the following compound as
viewed down the indicated bond?
H Br
HCl H
Br
Cl
H
Cl H
HBr
Cl H
H
Br
Cl
Br
A. B. C. D.
35. Which of the following is a Newman projection for the following compound as
viewed down the indicated bond?
H
HCl H
Cl
Cl H
H
Cl
H
Cl A. B. C. D.
36. Which of the following is a Newman projection for the following compound as
viewed down the indicated bond?
H Et
Et
HH
Et
Et Et
H
Et
H
H
H
H
A. B. C. D.
37. Which of the following is a wedge and dash projection for the following Newman
projection?
H Br
HBr Br
Br
Br
Br
Br
Br
Br
Br
A. B. C. D.
38. Which of the following is a wedge and dash projection for the following Newman
projection?
H
Et
EtH
H
A. B. C. D.
39. Which of the following is a wedge and dash projection for the following Newman
projection?
A. B. C. D.
Et
H H
H
40. Draw a wedge and dash projection of the following Newman projection.
H Br
HBr
41. Draw a wedge and dash projection of the following Newman projection.
Et
H H
H
42. Draw a wedge and dash projection of the following Newman projection.
Et
H H
Cl
43. Draw the Newman projection for the eclipsed form of propane.
44. Which of the following is a Newman projection of an eclipsed conformer?
H H
HH
A. B. C. D.
H
H
H
H
H
H H
H
HH
H
H
H
H
45. Which of the following is a Newman projection of a staggered conformer?
H H
HH
A. B. C. D.
H
H
H
H
H
H
H
H
H
H
H
H
46. Draw an energy diagram for propane.
47. What is the eclipsing cost of Br and H if the energy difference between the
staggered and eclipsed conformations of bromoethane is 13 kJ/mol?
48. What is the energy difference between the staggered and eclipsed conformations
of 2,2,-dimethylpropane if the eclipsing cost of Me and H is 6 kJ/mol?
49. Which of the following is a gauche conformer?
H H
HH
A. B. C. D.
H
H
H
H
H
H
H
H
H
H
H
H
50. Which of the following is an anti conformer?
H H
HH
A. B. C. D.
H
H
H
H
H
H
H
H
H
H
H
H
51. Draw the Newman projection of the anti conformer of the following compound.
Cl
52. Draw the gauche conformer of the following compound.
Cl
53. Draw the lowest energy conformer of the following compound.
54. Draw the lowest energy conformer of the following compound.
Br
Br
55. Draw the lowest energy conformer of the following compound.
56. Draw an energy diagram for rotation around the indicated bond of the following
compound.
Br
