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Organic Chemistry 4th Edition By Janice Smith – Test Bank 

 

 

 

Chapter 1: Structure and Bonding

 

1. What is the ground-state electronic configuration of a carbon atom?
A)  1s2, 2s2, 2p5    B)  1s2, 2s2, 2p2    C)  1s2, 2s2, 2p6    D)  1s2, 2s2, 2p4

 

2. What is the ground-state electronic configuration of a fluorine atom?
A)  1s2, 2s2, 2p2    B)  1s2, 2s2, 2p3    C)  1s2, 2s2, 2p4    D)  1s2, 2s2, 2p5

 

3. What is the ground-state electronic configuration of a magnesium cation (Mg2+)?
A) 1s2, 2s2, 2p6 C) 1s2, 2s2, 2p6, 3s2
B) 1s2, 2s2, 2p6, 3s1 D) 1s2, 2s2, 2p6, 3s2, 3p2

 

4. What is the ground-state electronic configuration of a chlorine anion (Cl)?
A) 1s2, 2s2, 2p6 C) 1s2, 2s2, 2p6, 3s2, 3p5
B) 1s2, 2s2, 2p6, 3s2, 3p6 D) 1s2, 2s2, 2p6, 3s2, 3p4

 

5. Which of the following statements about valence electrons is true?
A) They are the most tightly held electrons.
B) They do not participate in chemical reactions.
C) They are the outermost electrons.
D) They reveal the period number of a second-row element.

 

6. Which of the following statements about bonding is true?
A) Covalent bonds result from the transfer of electrons from one element to another.
B) Ionic bonds result from the transfer of electrons from a metal to a non-metal.
C) Ionic bonds result from the sharing of electrons between two non-metals.
D) Covalent bonds result from the sharing of electrons between two metals.

 

7. Which of the following would you expect to have ionic bonds?
A)  CO    B)  FBr    C)  NF3    D)  NaCl

 

 

 

8. Which of the following molecules has nonpolar covalent bonds?
A)  HCl    B)  N2    C)  CHCl3    D)  NO

 

9. Which of the following molecules contain both covalent and ionic bonds?

 

A)  I, II    B)  I, IV    C)  II, III    D)  II, IV

 

10. Arrange the following bonds in decreasing order of ionic character, putting the most ionic first.

 

A) I > II > III > IV C) IV > III > II > I
B) IV > II > I > III D) IV > II > III > I

 

11. Which of the following statements correctly describes the typical number of bonds for carbon, nitrogen, and oxygen in most neutral organic molecules?
A) Carbon forms 4 covalent bonds, nitrogen forms 2 covalent bonds and oxygen forms 3 covalent bonds.
B) Carbon forms 4 covalent bonds, nitrogen forms 3 covalent bonds and oxygen forms 2 covalent bonds.
C) Carbon forms 4 covalent bonds, nitrogen forms 5 covalent bonds and oxygen forms 2 covalent bonds.
D) Carbon forms 4 covalent bonds, nitrogen forms 5 covalent bonds and oxygen forms 4 covalent bonds.

 

12. Which is not an acceptable Lewis structure for the anion CH2NCO?

 

A)  I    B)  II    C)  III    D)  IV

 

13. Which of the following Lewis structures is correct?

 

A)  I    B)  II    C)  III    D)  IV

 

14. Which of the following Lewis structures is correct?

 

A)  I, II    B)  I, III    C)  II, III    D)  III, IV

 

15. Which is the correct Lewis structure for acetic acid (CH3CO2H)?

 

A)  I    B)  II    C)  III    D)  IV

 

16. In which of the following ions does carbon have a formal charge?

 

A)  I    B)  II    C)  III    D)  None of the above

 

17. In which of the following ions does carbon have a formal charge?

 

A)  I    B)  II    C)  III    D)  None of the above

 

18. What is the formal charge of carbon in carbon monoxide (CO) when drawn with a triple bond?
A)  0    B)  -2    C)  -1    D)  +1

 

19. Which of the following statements about constitutional isomers is true?
A) Constitutional isomers are different molecules having different molecular formula.
B) Constitutional isomers are different molecules having same molecular formula.
C) Constitutional isomers are same molecules having different molecular formula.
D) Constitutional isomers are same molecules having the same molecular formula.

 

20. How many constitutional isomers are there for a molecule having the molecular formula C2H6O?
A)  1    B)  2    C)  3    D)  4

 

21. How many constitutional isomers are there for a molecule having the molecular C3H8O?
A)  1    B)  2    C)  3    D)  4

 

22. How many constitutional isomers are there for a molecule having the molecular formula C3H6?
A)  1    B)  2    C)  3    D)  4

 

23. How many constitutional isomers are there for a molecule having the molecular formula C2H4Cl2?
A)  1    B)  2    C)  3    D)  4

 

24. How many different isomers are there for a compound having the molecular formula C3H6O?
A)  4    B)  5    C)  6    D)  7

 

25. Which of the following molecules are constitutional isomers?

 

A)  I, II, IV    B)  II, III, IV    C)  I, III, IV    D)  I, II, III

 

26. Which of the following compounds has an atom with an unfilled valence shell of electrons?
A)  H2O    B)  BCl3    C)  CH4    D)  CO2

 

27. Which of the following statements about resonance structures is true?
A) Resonance structures have the same placement of electrons but different arrangement of atoms.
B) Resonance structures have the same placement of atoms but different arrangement of electrons.
C) Resonance structures have the same placement of atoms and the same arrangement of electrons.
D) Resonance structures have different placement of atoms and different arrangement of electrons.

 

28. Which of the following statements about resonance structures is not true?
A) There is no movement of electrons from one form to another.
B) Resonance structures are not isomers.
C) Resonance structures differ only in the arrangement of electrons.
D) Resonance structures are in equilibrium with each other.

 

29. Which of the following pair does not represent resonance structures?

 

A)  I    B)  II    C)  III    D)  IV

 

30. What 2 things will change between two resonance structures?
A) The position of multiple bonds and non-bonded electrons.
B) The position of multiple bonds and single bonds.
C) The placement of atoms and single bonds.
D) The placement of atoms and non-bonded electrons.

 

31. Which of the following is a resonance structure of the compound below?

 

A)  I    B)  II    C)  III    D)  IV

 

32. Which of the following resonance structures is the least important contributor to the resonance hybrid of the formate anion, HCOO?

 

A)  I    B)  II    C)  III    D)  IV

 

33. Rank the following in order of decreasing importance as contributing structures to the resonance hybrid of formaldehyde, H2CO.

 

A)  I > II > III    B)  I > III > II    C)  II > I > III    D)  III > II > I

 

34. Follow the curved arrows to draw the second resonance structure for the ion below.

 

A)  I    B)  II    C)  III    D)  IV

 

35. Which is more important in each pair of contributing resonance structures?

 

A)  II, IV, V    B)  II, III, V    C)  II, III, VI    D)  I, IV, V

 

36. What is the approximate value of the H-C-H bond angle in methane, CH4?
A)  90°    B)  109.5°    C)  120°    D)  180°

 

37. What is the approximate C-C-C bond angle in propene, CH3CH=CH2?
A)  90°    B)  109.5°    C)  120°    D)  180°

 

38. What is the approximate H-C-O bond angle in formaldehyde, H2CO?
A)  90°    B)  109.5°    C)  120°    D)  180°

 

39. Determine the electron geometry around the indicated atom in each species.

 

A) I = Linear; II = tetrahedral; III = trigonal planar; IV = tetrahedral
B) I = Linear; II = tetrahedral; III = trigonal planar; IV = linear
C) I = Trigonal planar; II = linear; III = tetrahedral; IV = trigonal planar
D) I = Tetrahedral; II = trigonal planar; III = linear; IV = tetrahedral

 

40. What is the approximate bond angle for the C-C-N bond in acetonitrile, CH3CN?
A)  90°    B)  109.5°    C)  120°    D)  180°

 

41. Which of the following is the appropriate conversion of the condensed structure, CH3COCH3, to a Lewis structure?

 

A)  I    B)  II    C)  III    D)  IV

 

42. Which of the following is the appropriate conversion of (CH3)2CHCH2CHClCH3 to a skeletal structure?

 

A)  I    B)  II    C)  III    D)  IV

 

43. Which of the following is the appropriate conversion of (CH3)4C to a skeletal structure?

 

A)  I    B)  II    C)  III    D)  IV

 

44. What is the condensed formula of the compound below?

 

A)  I    B)  II    C)  III    D)  IV

 

45. Which of the following is the appropriate conversion of (CH3)2CHOCH2CH2CH2OH to a skeletal structure?

 

A)  I    B)  II    C)  III    D)  IV

 

46. Convert the following skeletal structure to a condensed structure.

 

A)  I    B)  II    C)  III    D)  IV

 

47. Avobenzone is an active ingredient in some common sunscreens.  Which of the following is the correct molecular formula for avobenzone?

 

A)  C22O22O3    B)  C20H22O3    C)  C21H23O3    D)  C20H24O3

 

48. In which structure is the hybridization incorrect?

 

A)  I    B)  II    C)  III    D)  IV

 

49. What is the hybridization for each of the indicated atoms in the following compound?

 

A) I = sp2; II = sp2; III = sp2. C) I = sp; II = sp2; III = sp3.
B) I = sp2; II = sp3; III = sp3. D) I = sp2; II = sp2; III = sp3.

 

50. What is the hybridization of the carbon atom in the methyl cation, (CH3+)?
A)  sp3    B)  sp2    C)  sp    D)  p

 

51. What is the hybridization of the nitrogen atom in the ammonium cation, NH4+?
A)  sp3    B)  sp2    C)  sp    D)  p

 

52. Which atomic orbitals overlap to form the C-H s bonding molecular orbitals of ethane, CH3CH3?
A)  Csp2 + H1s    B)  Csp3 + H1s    C)  C2p + H1s    D)  Csp + H1s

 

53. Which atomic orbitals overlap to form the C-H s bonding molecular orbitals of ethylene, H2C=CH2?
A)  C2p + H1s    B)  Csp + H1s    C)  Csp3 + H1s    D)  Csp2 + H1s

 

54. Which atomic orbitals overlap to form the carbon-carbon s and p bonding molecular orbitals of ethylene, H2C=CH2?
A) Csp3 + Csp3, and C2p + C2p C) Csp2 + Csp2, and C2p + C2p
B) Csp3 + Csp3, and Csp2 + Csp2 D) Csp2 + Csp2, and Csp2 + Csp2

 

55. Which atomic orbitals overlap to form the C-H s bonding molecular orbitals of acetylene, C2H2?
A)  Csp + H1s    B)  C2p +H1s    C)  Csp3 + H1s    D)  Csp2 + H1s

 

56. Which atomic orbitals overlap to form the carbon-carbon s bonding molecular orbital of acetylene, C2H2?
A)  Csp2 + Csp2    B)  Csp + Csp    C)  Csp3 + Csp3    D)  C2p + C2p

 

57. When forming molecular orbitals from atomic orbitals, what is the order of increasing C-H bond strength for the following.

 

A)  II < I < III    B)  III < I < II    C)  III < II < I    D)  I < II < III

 

58. What is the order of decreasing bond length for a C-C bond comprised of the following molecular orbitals?

 

A)  I > III > II    B)  I > II > III    C)  III > II > I    D)  II > III > I

 

59. Which of the following statements about electronegativity and the periodic table is true?
A) Electronegativity decreases across a row of the periodic table.
B) Electronegativity increases down a column of the periodic table.
C) Electronegativity increases across a row of the periodic table.
D) Electronegativity does not change down a column of the periodic table.

 

60. Rank the following atoms in order of increasing electronegativity, putting the least electronegative first.

 

A) I < II < III < IV C) III < II < IV < I
B) I < IV < II < III D) I < II < IV < III

 

61. Rank the following atoms in order of decreasing electronegativity, putting the most electronegative first.

 

A) I > IV > II > III C) III > IV > II > I
B) II > III > IV > I D) III > II > IV > I

 

62. Which molecule has the greatest difference in electronegativity (DE) between the two different elements?
A)  CO2    B)  H2S    C)  NH3    D)  H2O

 

63. Which compound contains the most polar bond?

 

A)  I    B)  II    C)  III    D)  IV

 

64. Which of the following compounds are non-polar?

 

A)  I, IV    B)  I, II    C)  II, III    D)  II, IV

 

65. Which of the following molecules has non-polar covalent bonds?
A)  CO2    B)  N2    C)  CCl4    D)  HF

 

66. Which of the following molecules has polar covalent bonds?
A)  MgO    B)  NH3    C)  Cl2    D)  NaBr

 

67. Which of the following covalent bonds has the largest dipole moment?
A)  C-H    B)  C-C    C)  C-O    D)  H-F

 

68. Which of the following molecules has the smallest dipole moment?
A)  CO2    B)  HCl    C)  H2O    D)  NH3

 

69. Which of the following molecules does not have a net dipole moment of zero?
A)  CCl4    B)  BF3    C)  CO2    D)  NH3

 

70. Which of the following molecules has a net dipole moment of zero?

 

A)  I    B)  II    C)  III    D)  IV

 

Chapter 2: Acids and Bases

 

1. Which of the following statements is a correct definition for a Brønsted-Lowry acid?
A) Proton acceptor C) Electron pair acceptor
B) Electron pair donor D) Proton donor

 

2. Which of the following statements about a Brønsted-Lowry base is true?
A) The net charge may be zero, positive, or negative.
B) All Brønsted-Lowry bases contain a lone pair of electrons or a p bond.
C) All Brønsted-Lowry bases contain a proton.
D) The net charge may be zero or positive.

 

3. Which of the following compounds is both a Brønsted-Lowry acid and base?

 

A)  I, II    B)  I, III    C)  II, IV    D)  I, IV

 

4. Which of the following species cannot act as both a Brønsted-Lowry acid and base?
A)  HCO3    B)  HSO4    C)  HO    D)  H2PO4

 

5. Which of the following species is not a Brønsted-Lowry base?
A)  BF3    B)  NH3    C)  H2O    D)  PO43-

 

6. Which of the following statements about Brønsted-Lowry acids and bases is true?
A) Loss of a proton from a base forms its conjugate acid.
B) Loss of a proton from an acid forms its conjugate base.
C) Gain of a proton by an acid forms its conjugate base.
D) Brønsted-Lowry acid-base reactions always result in the transfer of a proton from a base to an acid.

 

7. Which of the following species is the conjugate base of methanol, CH3OH?
A)  CH3OH2+    B)  CH3O    C)  CH3    D)  CH4

 

8. Which of the following species is the conjugate base of the hydronium ion, H3O+?
A)  H3O    B)  H2O    C)  H2O    D)  HO

 

9. Which of the following species is the conjugate acid of ammonia, NH3?
A)  H4N    B)  H3N+    C)  H2N    D)  H4N+

 

10. Which is the conjugate acid in the following reaction?

 

A)  I    B)  II    C)  III    D)  IV

 

11. Which is the conjugate base in the following reaction?

 

A)  I    B)  II    C)  III    D)  IV

 

12. Which is the conjugate acid in the following reaction?

 

A)  I    B)  II    C)  III    D)  IV

 

13. Which is the conjugate base in the following reaction?

 

A)  I    B)  II    C)  III    D)  IV

 

14. Which of the following statements about acid strength is true?
A) The stronger the acid, the further the equilibrium lies to the left.
B) The stronger the acid, the smaller the Ka.
C) The stronger the acid, the larger the pKa.
D) The stronger the acid, the smaller the pKa.

 

15. Which of the following compounds is the strongest acid?

 

A)  I    B)  II    C)  III    D)  IV

 

16. Which of the following compounds is the strongest acid?
A)  CH3OH    B)  BrCH2OH    C)  CH3NH2    D)  CH3Cl

 

17. Which of the following compounds is the weakest acid?
A)  HF    B)  HCl    C)  HBr    D)  HI

 

18. Which of the following compounds is the weakest acid?
A)  H2S    B)  PH3    C)  HCl    D)  SiH4

 

19. Which of the following species is the strongest base?
A)  HO    B)  H2N    C)  CH3COO    D)  Cl

 

20. Which of the following ranks the compounds in order of increasing basicity, putting the least basic first?
A) CH3NH2 < CH3OH < CH4 C) CH4 < CH3NH2 < CH3OH
B) CH3OH < CH3NH2 < CH4 D) CH4 < CH3OH < CH3NH2

 

21. Consider the following molecule with protons labeled, I-III.  Rank these protons in order of decreasing acidity, putting the most acidic first.

 

A)  I > II > III    B)  I > III > II    C)  III > II > I    D)  III > I > II

 

22. Rank the following compounds in order of increasing acidity, putting the least acidic first.

 

A) III < I < IV < II C) II < I < IV < III
B) III < IV < I < II D) III < I < II < IV

 

23. Rank the following compounds in order of increasing acidity, putting the least acidic first.

 

A) I < IV < III < II C) II < III < IV < I
B) I < III < IV < II D) II < IV < III < I

 

24. Rank the following compounds in order of decreasing acidity, putting the most acidic first.

 

A) IV > II > III > I C) I > II > IV > III
B) III > II > IV > I D) III > IV > II > I

 

25. Rank the following compounds in order of decreasing acidity, putting the most acidic first.

 

A) IV > II > III > I C) III > IV > II > I
B) IV > III > II > I D) III > IV > I > II

 

26. Rank the following conjugate bases in order of increasing basicity, putting the least basic first.

 

A)  II < I < III    B)  II < III < I    C)  I < II < III    D)  I < III < II

 

27. Rank the following conjugate bases in order of decreasing basicity, putting the most basic first.

 

A)  II > I > III    B)  I > II > III    C)  III > I > II    D)  III > II > I

 

28. Which of the following is the strongest base?
A)  CH3COCH3    B)  CH3COOH    C)  NH3    D)  H2O

 

29. What is the direction of equilibrium when acetylene (C2H2) reacts with H2N in an acid-base reaction?

 

A)  Left    B)  Right    C)  Neither    D)  Cannot be determined

 

30. What is the direction of equilibrium when acetylene (C2H2) reacts with ethoxide (CH3CH2O) in an acid-base reaction?

 

A)  Left    B)  Right    C)  Neither    D)  Cannot be determined

 

31. Which of the following statements explain why H2O is a stronger acid than CH4?
A) H2O can form hydrogen bonds while CH4 cannot.
B) H2O forms a less stable conjugate base, HO.
C) CH4 forms a more stable conjugate base, CH3.
D) H2O forms a more stable conjugate base, HO.

 

32. Which of the following statements explain why HBr is a stronger acid than HF?
A) Br is more stable than F because Br is larger than F.
B) Br is less stable than F because Br is larger than F.
C) Br is more stable than F because Br is less electronegative than F.
D) Br is less stable than F because Br is less electronegative than F.

 

33. Which of the following compounds has the lowest pKa?
A)  H2O    B)  H2S    C)  NH3    D)  CH4

 

34. Which of the following concepts can be used to explain the difference in acidity between acetic acid (CH3COOH) and ethanol (CH3CH2OH)?
A)  Hybridization    B)  Electronegativity    C)  Resonance    D)  Size

 

35. Which of the following concepts can be used to explain the difference in acidity between acetylene (C2H2) and ethylene (C2H4)?
A)  Size    B)  Resonance    C)  Inductive effect    D)  Hybridization

 

36. Which of the following concepts can be used to explain the difference in acidity between ethanol (CH3CH2OH) and 2-fluoroethanol (FCH2CH2OH)?
A)  Size    B)  Inductive effect    C)  Resonance    D)  Hybridization

 

37. Rank the following compounds in order of decreasing acidity, putting the most acidic first.

 

A)  I > II > III    B)  III > II > I    C)  II > III > I    D)  III > I > II

 

38. Which of the following statements about Lewis acids is true?
A) Lewis acids are proton donors.
B) Lewis acids are proton acceptors.
C) Lewis acids are electron pair donors.
D) Lewis acids are electron pair acceptors.

 

39. Which of the following statements about Lewis bases is true?
A) Lewis bases are electron pair acceptors.
B) Lewis bases are electron pair donors.
C) Lewis bases are proton donors.
D) Lewis bases are proton acceptors.

 

40. Which of the following is a Lewis acid but not a Brønsted-Lowry acid?
A)  CH3OH    B)  H2O    C)  CH3COOH    D)  BF3

 

41. Which of the following species can be both Lewis acid and Lewis base?

 

A)  I, III, IV    B)  I, II, IV    C)  II, III, IV    D)  I, II, III

 

42. What is the correct classification of the following compound?

 

CH3-O-CH3

A) Brønsted-Lowry acid and Lewis acid. C) Brønsted-Lowry base.
B) Brønsted-Lowry base and Lewis base. D) Lewis base.

 

43. Identify the Lewis acid in the following reaction.

 

A)  I    B)  II    C)  III    D)  IV

 

44. Identify the Lewis base in the following reaction.

 

A)  I    B)  II    C)  III    D)  IV

 

45. Which of the following compounds is not a Lewis acid?
A)  AlCl3    B)  HCl    C)  H2O    D)  CBr4

 

46. What is the role of methylchloride (CH3Cl) in the following reaction?

 

A) Lewis acid C) Brønsted-Lowry acid
B) Lewis base D) Brønsted-Lowry base

 

47. What is the electrophilic site in the following compounds?

 

A) I = Carbon; II = carbon; III = boron. C) I = Carbon; II = oxygen; III = boron.
B) I = Chlorine; II = carbon; III = boron. D) I = Carbon; II = carbon; III = fluorine.

 

48. What is the nucleophilic site in the following compounds?

 

A) I = Hydrogen; II = p electrons in bond; III = nitrogen.
B) I = Oxygen; II = carbon; III = nitrogen.
C) I = Hydrogen; II = carbon; III = carbon.
D) I = Oxygen; II = p electrons in bond; III = nitrogen.