PRACTICE PROBLEMS, CHAPTERS 1 - 3

(Covered from Ch. 3: Alkane and Alkyl Halide nomenclature only) 1. The atomic number of boron is 5. The correct electronic configuration of boron is: A. 1s22s3 B. 1s22p3 C. 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 __________.
H3C C H N H H

8. Which of the following are correct Lewis structures for nitric acid, HNO3?
O H N O A O H O B O N O H O C O N O

9. The formal charge on oxygen in dimethyl ether, CH3OCH3, is ________. 10. Which of the following choices represent(s) a pair of resonance forms?
H H B H CH3 C O CH3
and

H H3C C H

O C H
and

O H3C C H A C

H CH3 C O CH3

H C H C C N
and

H C H C N

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

H H CH 3 CH3

H OH H H

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.

H P C H

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

H H B H
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?

CN

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?

Cl Cl

H Br

Cl Br

H Cl

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

CH 3 CH 3

H H

CH 3 H

CH3 H

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

CH3

CH2 H

H CH3

CH 3 H

CH 2 CH 3 H

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

O OH H
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?

CN

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?

O C H

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.

CH(CH 3)2
CH3 (CH2 )5CHCH2 CH2CH3 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.

CH 3 CH 2CH 3
61. Provide an acceptable name for the compound shown below.

CH 3 CH 3 Br
62. Provide an acceptable IUPAC name for CH3CH2CH2C(CH3)2I. 63. Provide an acceptable IUPAC name for the compound shown below.

Cl Cl

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

ANSWERS
1. C 4. 2. Three: 2px, 2py, 2pz 3. Six

H O B H O O H

5.

CH3 CH3 C CH3 O H

6.

H H C H
7. +1 11. 8. B 9. Zero 10. B and C only. Atoms have been moved in A, which is not allowed.

or

CH3

OH
or

OH CH 3 CH 3

12. A 14.

13. TRUE

H P C H

15.
H H B H C N

16. False 18.

17. B

NH2
19. D 20. B 21. Molecular orbitals 27. 120 degrees 22. Sigma 23. Pi 24. B 25. 180 degrees 30. C 34. B

26. 109.5 degrees 31. sp2 32. sp

28. sp2/120

29. sp3/tetrahedral

33. Six. The triple bond contains two of them.

35. The alcohol, CH3CH2CH2OH, has the higher boiling point, since it is capable of intermolecular hydrogen bonding. The ether is not. 36. CH3CH2CH2NH2 has the higher boiling point, since it is capable of intermolecular hydrogen bonding. 37. The alcohol, CH3CH2OH, is more soluble in water since it can form a hydrogen bond to water and accept a hydrogen bond from water. The ether, CH3OCH3, can only accept a hydrogen bond from water. 38. The amine, (CH3)2NH, is more soluble in water since it can hydrogen bond with water. Alkanes are not capable of hydrogen bonding with water. 39. Structural isomers: same molecular formulas, but different atom connectivities. 40. Structural isomers 41. Geometric (cis-trans) isomers: They owe their existence to hindered rotation around the pi-bond. 42. Structural isomers 43. Structural isomers

44. Geometric (cis-trans) isomers:

H H H
Represents a carbon atom attached to the C=C bond

Cis relationship 45. B 46. E

Trans relationship 47. E

48. Carboxilic acid:

O OH

49. 14 sigma bonds and 3 pi bonds. You must count every C-C and C-H bond. The CN bond is a triple bond, which alone accounts for two pi and one sigma bond.

50. 6 sigma bonds and 3 pi bonds. 52.

51. E. There is no sp oxygen in the molecule.

pentane, or n-pentane 53. 2,5-dimethylheptane

isopentane
7 6 5 3 4 2 1

neopentane

54. 2,2-dimethyl-5-(1-methylpropyl)nonane
8 7 6 4 3 (3) (2) 2 1

5 (1)

55. 4-(1-methylethyl)decane
9 10 8 7 6 5 4 3 1 2

CH(CH 3)2
CH3 (CH2 )5CHCH2 CH2 CH3

(1)

(2)

56. 3-ethyl-7-methyl-5-propylnonane

57.

58.

59.

60. trans-1-ethyl-2-methylcyclopentane 61. 1-bromo-4,4-dimethylcyclohexane 62. 2-iodo-2-methylpentane 63. cis-1, 2-dichlorocyclopentane 64.

(CH3)2CH-I

65. CH3CH2CH2CH(CH3)CH2CH2Br 66. B (Isoproyl chloride). Chlorine is attached to a secondary carbon.

Cl
67. E (Isobutyl chloride). Chlorine is attached to a primary carbon:

Cl