1.1: Chapter 1-3 Exercises

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1. The atomic number of boron is 5. The correct electronic configuration of boron is:

A. 1s²2s³ B. 1s²2p³C. 1s²2s²2p¹ D. 2s²2p³ E. 1s²2s²3s¹

2. How many distinct p orbitals exist in the second electron shell, where n = 2?

3. An oxygen atom has __________ valence electrons.

4. Draw a correct Lewis structure for boric acid, B(OH)₃.

5. Draw a correct Lewis structure for t-butanol, (CH₃)₃COH.

6. Draw a correct Lewis structure for acetonitrile, CH₃CN.

7. The formal charge on nitrogen in the compound below is __________.

8. Which of the following are correct Lewis structures for nitric acid, HNO₃?

9. The formal charge on oxygen in dimethyl ether, CH₃OCH₃, is ________.

10. Which of the following choices represent(s) a pair of resonance forms?

11. Draw an acceptable line-angle formula for the molecule shown

12. Orbitals which are equal in energy are referred to as __________.

A. degenerate B. polar C. nodes D. filled E. nonpolar

13. When filling two or more orbitals of the same energy with electrons, the electrons will go into different orbitals rather than pair up in the same orbital. ___True ___False

14. One or more of the atoms in the structure shown should have nonzero formal charges. Redraw the structure and indicate any such charges.

15. One or more of the atoms in the structure shown should have nonzero formal charges. Redraw the structure and indicate any such charges.

16. When a molecule can best be represented as a series of resonance forms, each of these forms always contributes to the same degree in the hybrid.

___True ___False

17. The __________ tells us that each orbital can hold a maximum of 2 electrons.

A. Aufbau principle

B. Pauli exclusion principle

C. Hund's rule principle

D. LeChatelier principle

E. Uncertainty principle

18. Draw a line-angle formula for (CH₃)₂CHCH₂CH₂NH₂

19. In the compound sodium methoxide (NaOCH₃), there is __________ bonding.

A. ionic

B. polar covalent

C. nonpolar covalent

D. a mixture of ionic and covalent

E. resonance stabilized

20. A carbon-hydrogen bond in ethane (CH₃CH₃) is best described as __________.

A. highly polar

B. essentially nonpolar

C. ionic

D. a multiple bond

E. resonance stabilized

21. What kind of orbitals result when orbitals of different atoms interact?

22. What kind of molecular orbital (sigma or pi) results when the two atomic orbitals shown below approach each other head to head as indicated?

23. What kind of molecular orbital (sigma or pi) results when the two atomic orbitals shown below approach each other sideways as indicated?

24. Which of the following statements about pi molecular orbitals is/are correct?

A. They are cylindrical.

B. Most of their electron density is centered above and below the internuclear axis.

C. When two atoms are connected by a double bond, both of those bonds are pi bonds.

D. Both B and C.

E. A, B, and C.

25. The HCN bond angle in hydrogen cyanide (HCN) is __________ degrees.

26. The HCH bond angle in propane is __________ degrees.

27. The CCO bond angle in acetone (CH₃COCH₃) is __________ degrees.

28. In boron trifluoride (BF₃) the boron atom is ____ hybridized and the FBF bond angle is ______ degrees.

29. In triethylamine [(CH₃CH₂)₃N] the N atom is ____ hybridized and the geometry of the N atom is ________.

30. Structures which differ only in rotations about a single bond are called __________.

A. Structural isomers B. Geometric isomers C. Conformers D. Resonance structures

31. What is the hybridization of the oxygen atom in CH₃CHO?

32. What is the hybridization of the ntrogen atom in (CH₃)₂CHCN?

33. How many pi bonds are present in the following molecule?

34. Which of the molecules below can be properly called an ether?

A. CH₃CH₂CH(CH₃)₂

B. CH₃OCH₂CH₂CH₃

C. CH₃COOH

D. CH₃COOCH₃

E. HCCCH₃

35. Which of the molecules below has the higher boiling point? Briefly explain your choice.

CH₃CH₂CH₂OH or CH₃CH₂OCH₃

36. Which of the molecules below has the higher boiling point? Briefly explain your choice.

(CH₃)₃N or CH₃CH₂CH₂NH₂

37. Which compound is more soluble in water? Briefly explain your choice.

CH₃OCH₃ or CH₃CH₂OH

38. Which compound is more soluble in water? Briefly explain your choice.

(CH₃)2NH or CH₃CH₂CH₃

39. Are the two compounds shown best described as geometric isomers, structural isomers, or not isomeric?

40. Are the two compounds shown best described as geometric isomers, structural isomers, or not isomeric?

41. Are the two compounds shown best described as geometric isomers, structural isomers, or not isomeric?

42. Are the two compounds shown best described as geometric isomers, structural isomers, or not isomeric?

43. Are the two compounds shown best described as geometric isomers, structural isomers, or not isomeric?

44. Are the two compounds shown best described as geometric isomers, structural isomers, or not isomeric?

45. Which one of the molecules shown below has no net molecular dipole moment?

A. CH₃Cl B. H₂C=CH₂ C. CH₂O D. CH₂Cl₂ E. CH₃OH

46. Choose the term below which best describes the geometry of acetylene (HCCH).

A. trigonal bipyramidal

B. trigonal

C. tetrahedral

D. square planar

E. linear

47. Which of the functional groups below contain a hydroxyl group as a part of their structure?

A. aldehyde B. alcohol C. carboxylic acid D. amine E. B and C

48. What is the name of the functional group found in the molecule CH₃CH₂COOH?

49. How many sigma bonds and how many pi bonds are present in the molecule shown?

50. How many sigma bonds and how many pi bonds are present in acrylonitrile, CH2=CHCN?

51. Which of the following statements concerning the cyclic molecule shown is not true?

A. It contains a pi molecular orbital formed by the overlap of a carbon p orbital with an oxygen p orbital.

B. It contains a sigma molecular orbital formed by the overlap of two carbon sp² orbitals.

C. It contains a sigma molecular orbital formed by the overlap of two carbon sp³ orbitals.

D. It contains a pi molecular orbital formed by the overlap of two carbon p orbitals.

E. It contains a sigma molecular orbital formed by the overlap of a carbon p orbital with an oxygen sp³ orbital.

52. Give structures for the 3 isomers with molecular formula C₅H₁₂ and provide the common name of each.

53. Provide an acceptable IUPAC name for the alkane shown below.

54. Provide an acceptable IUPAC name for the alkane shown below.

55. Provide an acceptable IUPAC name for the alkane shown below.

56. Provide an acceptable IUPAC name for the alkane shown below.

57. Draw an acceptable structure for 4-ethyl-6-(1,2-dimethylpropyl)decane.

58. Draw an acceptable structure for 3-ethyl-3-methylhexane.

59. Draw an acceptable structure for 6-ethyl-2,6,7-trimethyl-5-propylnonane.

60. Give the IUPAC name for the cycloalkane shown below.

61. Provide an acceptable name for the compound shown below.

62. Provide an acceptable IUPAC name for CH₃CH₂CH₂C(CH₃)₂I.

63. Provide an acceptable IUPAC name for the compound shown below.

64. Provide the structure of isopropyl iodide.

65. Provide the structure of 1-bromo-3-methylhexane.

66. Which of the following is a secondary alkyl halide?

A. methyl bromide

B. isopropyl chloride

C. t-butyl iodide

D. propyl bromide

E. isobutyl chloride

67. Which of the following is a primary alkyl halide?

A. methyl bromide

B. isopropyl bromide

C. t-butyl iodide

D. cyclohexyl bromide

E. isobutyl chloride