Organic Chemistry, 3rd Edition Test Bank

Klein, Organic Chemistry 3e Chapter 2 1. What is the molecular formula for the following compound? A. B. C. D. E. C2H6O C4H6O C4H10O C2H4O None of these Answer: C Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Easy 2. Which of the following compounds have a molecular formula of C2H6O? A. B. C. D. E. I II III IV Both I and III Answer: E Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Easy 3. Which of the following is the correct condensed structure for the following compound? A. B. C. D. E. CH3CHCH3CH2OH CH3CH2CH2OH (CH3)2CHCH2OH CH3CH2CH2OCH3 CH3CH3CHCH2OH Answer: C Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Easy 4. Which of the following is the correct condensed structure for the following compound? A. B. C. D. E. CH3CHOHCH2CHClCH3 CH3CHOH(CH2)2CHClCH3 (CH3)2CHOHCH2CH2Cl HOCH3CHCH2CH2CH3CHCl CH3C2H4CH3OHCl Answer: B Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Easy 5. Which of the following is the correct condensed structure for the following compound? A. B. C. D. E. CH2=CH(CH2)3C(CH3)3 CH(CH2)4C(CH3)3 (CH3)2CH(CH2) 4CH3 CH2CH(CH2)3C(CH3)3 (CH)3(CH2)3C(CH3)3 Answer: A Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Medium 6. Which of the following is the correct condensed structure for the following compound? A. B. C. D. E. CH3C2(CH2)3C(CH3)3 CH3CC(CH2)3C(CH3)2CH3 (CH3)3C2(CH2)3CH3 CH3C≡C(CH2)3C(CH3)3 CH3CC(CH2)3C(CH3)3 Answer: D Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Medium 7. Which of the following is the correct condensed structure for the following compound? A. B. C. D. E. CH3C(CH3)2(CH2)2(CH)BrC(CH3)2 CH3CH3CH3C(CH2)2C(CH3)2CHBr (CH3)3C(CH2)3BrCHCH3CH3 CH3CH3CH3C(CH2)2CHBrCHCH3CH3 (CH3)3C(CH2)2CHBrCH(CH3)2 Answer: E Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Medium 8. Provide the correct condensed structure for the following compound. Answer: (CH3)3C(CH2)2OCH(CH2CH3)2 Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Hard 9. Provide the correct condensed structure for the following compound. Answer: (CH3)2N(CH2)3CH(CH3)2 Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Hard 10. Which of the following is the correct molecular formula for (CH3CH2)4C? A. B. C. D. E. C8H20 C5H20 C9H20 C6H5 C3H20 Answer: C Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Easy 11. Which of the following is the correct Lewis structure for CH3(CH2)2NH2? A. B. C. D. E. I II III IV Both II and III Answer: C Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Easy 12. Which of the following is the correct Lewis structure for CH3(CH2)2OH? A. B. C. D. E. I II III IV Both II and III Answer: B Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Easy 13. Which of the following is the correct Lewis structure for (CH3)2CHCH2OH? A. B. C. D. E. I II III IV Both III and IV Answer: C Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Easy 14. Which of the following is the correct Lewis structure for (CH3)3C(CH2)2NHCH3? A. B. C. D. E. I II III IV V Answer: D Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Medium 15. Draw the Lewis structure for CH3C≡C(CH2)3C(CH3)3. Answer: Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Medium 16. Draw the Lewis structure for (CH3)3C(CH2)2OCH(CH2CH3)2. Answer: Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Hard 17. Identify the partially condensed structure for CH3CH2OCH2CH3. A. B. C. D. E. I II III IV V Answer: A Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Easy 18. Identify the partially condensed structure for CH3CH2CH2NH2. Answer: A Learning Objective: 2.1 Convert molecular representations from one drawing style to another, including Lewis structures, partially condensed structures, condensed structures, and molecular formulas Difficulty: Easy 19. Which of the following bond-line structures are of the same compound? A. B. C. D. E. I and II II and III III and IV II and IV None of these Answer: D Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy 20. Which of the following bond-line structures are of the same compound? A. B. C. D. E. I and III II and III III and IV II and IV None of these Answer: A Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy 21. How many hydrogen atoms are connected to the indicated carbon atom? A. B. C. D. E. one two three four none Answer: E Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy 22. How many hydrogen atoms are connected to the indicated carbon atom? A. B. one two C. D. E. three four none Answer: A Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy 23. How many hydrogen atoms are connected to the indicated carbon atom? A. B. C. D. E. one two three four none Answer: B Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy 24. How many hydrogen atoms are connected to the indicated carbon atom? A. B. C. D. E. one two three four none Answer: A Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy 25. How many hydrogen atoms are connected to the indicated carbon atom? A. B. C. D. E. one two three four none Answer: E Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy 26. For the following equation, how many hydrogen atoms are added or lost? A. B. C. D. E. added one added two lost one lost two no change Answer: D Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy 27. For the following equation, how many hydrogen atoms are added or lost? A. B. C. D. E. added one added two lost one lost two no change Answer: B Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy 28. For the following equation, how many hydrogen atoms are added or lost? A. B. C. D. E. added one added two lost one lost two no change Answer: E Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy 29. For the following equation, how many hydrogen atoms are added or lost? A. B. C. D. E. added one added two lost one lost two no change Answer: E Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy 30. For the following equation, how many hydrogen atoms are added or lost? A. B. C. D. E. added one added two lost one lost two no change Answer: D Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Medium 31. For the following equation, how many hydrogen atoms are added or lost? A. B. C. D. E. added one added two lost one lost two no change Answer: E Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Medium 32. Which of the following is the correct Lewis structure for the following compound? A. B. C. D. E. I II III IV none of these Answer: B Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy 33. Which of the following is the correct bond-line structure for (CH3)4C? A. B. C. D. E. I II III IV None of these Answer: C Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy 34. Which of the following is the correct bond-line structure for (CH3)2CHCH2CH3? A. B. C. D. E. I II III IV None of these Answer: A Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Easy 35. Which of the following (CH3)2CHCH2C(CH3)3? A. B. C. D. E. I II III IV None of these is the correct bond-line structure for Answer: B Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Medium 36. Which of the following CH3C≡C(CH2)2CH(CH3)2? A. B. C. D. E. I II III IV None of these is the correct bond-line structure for Answer: D Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Medium 37. Which of the following is CH3CHOH(CH2)2CH(CH2CH3) 2? A. B. C. D. E. I II III IV V the correct bond-line structure for Answer: B Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Medium 38. Draw a bond-line structure for CH3CH2O(CH2)2CH(CH3)2. Answer: Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Hard 39. Draw a bond-line structure for (CH3)2N(CH2)3CH(CH3)2. Answer: Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Hard 40. Draw a bond-line structure for CH3C≡C(CH2)3C(CH3)2CH2OCH3. Answer: Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Hard 41. Draw a bond-line structure for each constitutional isomer with a molecular formula of C2H4O. Answer: Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Hard 42. Draw a bond-line structure for each constitutional isomer with a molecular formula of C3H8O. Answer: Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Hard 43. Provide a condensed structure for the following compound. Answer: (CH3)3CCH2CH(CH2CH3)(CH2)2CH(CH3)CH2CH3 Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Hard 44. Provide a condensed structure for the following compound. Answer: (CH3)3C(CH2)2CH(NH2)CH=CHCH3 Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Hard 45. Draw a bond-line structure for each constitutional isomer with molecular formula C4H10O. Answer: Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Hard 46. Draw a bond-line structure for each constitutional isomer with molecular formula C4H11N. Answer: Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Medium 47. Naproxen, sold under the trade name Aleve, has the following structure. What is the molecular formula for naproxen? Answer: C14H14O3 Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Hard 48. AZT, used in the treatment of AIDS, has the following structure. What is the molecular formula for AZT? Answer: C10H13N5O4 Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Hard 49. Capsaicin, found in peppers, has the following structure. What is the molecular formula for capsaicin? Answer: C18H27NO3 Learning Objective: 2.2 Demonstrate how to read and draw bond-line structures through converting other styles of molecular representation into bond-line structures and vice versa Difficulty: Hard 50. Which of the following compounds contain an alcohol functional group? A. B. C. D. E. I II III IV None of these Answer: C Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 51. Which of the following compounds contain an alkene functional group? A. B. C. D. E. I II III IV None of these Answer: A Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 52. Which of the following compounds contain an amine functional group? A. B. C. D. E. I II III IV None of these Answer: D Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 53. Which of the following compounds contain a ketone functional group? A. B. C. D. E. I II III IV All of these Answer: A Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 54. Which of the following compounds contain an aromatic ring? A. B. C. D. E. I II III IV Both III and IV Answer: C Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 55. Which of the following compounds contain an ester functional group? A. B. C. D. E. I II III IV Both I and IV Answer: A Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 56. Which of the following compounds contain an amide functional group? A. B. C. D. E. I II III IV Both II and III Answer: B Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 57. Which of the following compounds contain an anhydride functional group? A. B. C. D. E. I II III IV none of the above Answer: C Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 58. Which of the following compounds contain an alkyne functional group? A. B. C. D. E. I II III IV none of the above Answer: A Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 59. Which of the following compounds contain a thiol functional group? A. B. C. D. E. I II III IV none of the above Answer: B Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 60. Which of the following compounds contain an alkyl halide functional group? A. B. C. D. E. I II III IV none of the above Answer: D Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Easy 61. What functional group(s) is (are) present in the following compound? A. B. C. D. E. ketone and alkene ketone and alkyne aldehyde and alkene aldehyde and alkyne ester and alkene Answer: C Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Medium 62. Which of the following compounds have both a ketone and an ester functional group? A. B. C. D. E. I II III IV V Answer: E Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Medium 63. Norethynodrel, a component of the first combined oral contraceptive, has the following structure. Identify the functional groups in Norethynodrel. Answer: Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Medium 64. Identify the functional groups in the following compound. Answer: Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Medium 65. Tamiflu®, the most effective antiviral drug used to treat avian influenza, has the following structure. Identify the functional groups in Tamiflu®. Answer: Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Hard 66. Aspartame, an artificial sweetener used in Equal® and diet beverages, has the following structure. Identify the functional groups in Aspartame. Answer: Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Hard 67. Draw all the constitutional isomers with a molecular formula of C3H6O and label the functional groups in each isomer. Answer: Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Hard 68. Amoxicillin, an antibiotic, has the following structure. Identify the functional groups in amoxicillin. Answer: Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Hard 69. Viracept, used in the treatment of HIV, has the following structure. Identify the functional groups in Viracept. Answer: Learning Objective: 2.3 Identify and draw the functional groups Difficulty: Hard 70. How many hydrogen atoms are connected to the indicated carbon atom? A. B. C. D. E. one two three four none Answer: B Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 71. How many hydrogen atoms are connected to the indicated carbon atom? A. B. C. D. E. one two three four none Answer: E Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 72. How many hydrogen atoms are connected to the indicated carbon atom? A. B. C. D. E. one two three four none Answer: A Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 73. How many hydrogen atoms are connected to the indicated carbon atom? A. B. C. D. E. one two three four none Answer: B Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 74. How many hydrogen atoms are connected to the indicated carbon atom? A. B. C. D. E. one two three four none Answer: E Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 75. How many hydrogen atoms are connected to the indicated carbon atom? A. B. C. D. E. one two three four none Answer: A Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 76. What is the formal charge on the indicated carbon atom? A. B. C. D. E. -2 -1 0 +1 +2 Answer: D Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 77. What is the formal charge on the indicated carbon atom? A. B. C. D. E. -2 -1 0 +1 +2 Answer: D Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 78. What is the formal charge on the indicated carbon atom? A. B. C. D. E. -2 -1 0 +1 +2 Answer: D Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 79. What is the formal charge on the indicated carbon atom? A. B. C. D. E. -2 -1 0 +1 +2 Answer: B Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 80. What is the formal charge on the indicated carbon atom? A. -2 B. C. D. E. -1 0 +1 +2 Answer: B Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 81. What is the formal charge on the indicated carbon atom? A. B. C. D. E. -2 -1 0 +1 +2 Answer: B Learning Objective: 2.4 Identify formal charges on carbon Difficulty: Easy 82. What is the formal charge on the oxygen atom in the following compound? A. B. C. D. E. +1 +2 -1 -2 0 Answer: A Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 83. What is the formal charge on the nitrogen atom in the following compound? A. B. C. D. E. -1 -2 +1 +2 0 Answer: C Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 84. What is the formal charge on the nitrogen atom in the following compound? A. B. C. D. E. +1 +2 -1 -2 0 Answer: A Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 85. What is the formal charge on the indicated oxygen atom in the following compound? A. B. C. D. E. +1 +2 -1 -2 0 Answer: E Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 86. What is the formal charge on the nitrogen atom in the following compound? A. B. C. D. E. +1 +2 -1 -2 0 Answer: E Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 87. Which of the following compounds have +1 as a formal charge on an oxygen atom? A. B. I II C. D. E. III IV Both I and IV Answer: B Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Medium 88. Which of the following compounds have +1 as a formal charge on the nitrogen atom? A. B. C. D. E. I II III IV Both I and II Answer: D Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Medium 89. Determine the formal charges on each atom except hydrogen. Answer: Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Medium 90. Diazomethane has the molecular formula CH2N2. Draw the preferred Lewis structure for diazomethane and assign formal charges to all atoms except hydrogen. Answer: Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Hard 91. Draw Lewis structure for the following compound. Answer: Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Medium 92. How many lone pairs of electrons are on the oxygen atom? A. B. C. D. E. one two three four none Answer: C Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 93. How many lone pairs of electrons are on the nitrogen atom? A. B. C. D. E. one two three four none Answer: B Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 94. How many lone pairs of electrons are on the oxygen atom? A. B. C. D. E. one two three four none Answer: B Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 95. How many lone pairs of electrons are on the nitrogen atom? A. B. C. D. E. one two three four none Answer: A Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 96. How many lone pairs of electrons are on the nitrogen atom? A. B. C. D. E. one two three four none Answer: E Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 97. How many lone pairs of electrons are on the indicated oxygen atom? A. B. C. D. E. one two three four none Answer: B Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 98. How many lone pairs of electrons are on the indicated oxygen atom? A. B. C. D. E. one two three four none Answer: A Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Medium 99. How many total lone pairs of electrons are in the following compound? A. B. C. D. E. one two three four none Answer: C Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Easy 100. Draw all lone pairs of electrons for the following compound. Answer: Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Medium 101. Draw all lone pairs of electrons for the following compound. Answer: Learning Objective: 2.5 Describe the relationship between the number of bonds, the number of lone pairs, and formal charge for oxygen and nitrogen atoms Difficulty: Medium 102. The indicated bond in the following compound is_____ of the paper. A. B. C. D. in the plane out of the plane behind the plane None of these Answer: B Learning Objective: 2.6 Describe how wedges and dashes are used to indicate threedimensional molecular structure Difficulty: Easy 103. The indicated bond in the following compound is_____ of the paper. A. B. C. D. in the plane out of the plane behind the plane None of these Answer: C Learning Objective: 2.6 Describe how wedges and dashes are used to indicate threedimensional molecular structure Difficulty: Easy 104. The indicated bond in the following compound is_____ of the paper. A. B. C. D. in the plane out of the plane behind the plane None of these Answer: C Learning Objective: 2.6 Describe how wedges and dashes are used to indicate threedimensional molecular structure Difficulty: Easy 105. Which of the following is a Fischer projection? A. B. C. D. E. I II III IV Both III and IV Answer: B Learning Objective: 2.6 Describe how wedges and dashes are used to indicate threedimensional molecular structure Difficulty: Easy 106. Which of the following is a Haworth projection? A. B. C. D. E. I II III IV Both III and IV Answer: C Learning Objective: 2.6 Describe how wedges and dashes are used to indicate threedimensional molecular structure Difficulty: Easy 107. Label the bonds that are out of the plane and behind the plane of the paper. Answer: Learning Objective: 2.6 Describe how wedges and dashes are used to indicate threedimensional molecular structure Difficulty: Medium 108. Which of the following pairs are resonance structures of each other? A. B. C. D. E. I II III IV None of these Answer: D Learning Objective: 2.7 Define “resonance,” describing the relationship between resonance and molecular orbital theory Difficulty: Easy 109. Which of the following pairs are resonance structures of each other? A. B. C. D. E. I II III IV None of these Answer: C Learning Objective: 2.7 Define “resonance,” describing the relationship between resonance and molecular orbital theory Difficulty: Easy 110. The spreading of positive or negative charge over two or more atoms in a compound is called_______. A. B. C. D. E. isomerism delocalization stereoisomerism localization None of these Answer: B Learning Objective: 2.7 Define “resonance,” describing the relationship between resonance and molecular orbital theory Difficulty: Easy 111. Delocalization of charge over two or more atoms _______ a molecule. A. B. C. D. E. destabilizes delocalizes localizes stabilizes None of these Answer: D Learning Objective: 2.7 Define “resonance,” describing the relationship between resonance and molecular orbital theory Difficulty: Easy 112. Resonance structures have _______ connectivity of atoms and _______ distribution of electrons. A. B. C. D. E. different, same same, same different, different same, different None of these Answer: D Learning Objective: 2.7 Define “resonance,” describing the relationship between resonance and molecular orbital theory Difficulty: Medium 113. What is a resonance hybrid? Answer: A molecule that can be represented by drawing two or more resonance structures is viewed as a resonance hybrid. Learning Objective: 2.7 Define “resonance,” describing the relationship between resonance and molecular orbital theory Difficulty: Medium 114. Which of the following violates the rules for curved arrows? A. B. C. D. E. I II III IV none of these Answer: A Learning Objective: 2.8 Demonstrate the used of curved arrows in drawing resonance structures, stating the two rules to be applied when drawing curved arrows Difficulty: Easy 115. Which of the following violates the rules for curved arrows? A. B. C. D. E. I II and IV I and III III and IV None of these Answer: C Learning Objective: 2.8 Demonstrate the used of curved arrows in drawing resonance structures, stating the two rules to be applied when drawing curved arrows Difficulty: Easy 116. Which of the following violates the rules for curved arrows? A. B. C. D. E. I and II III and IV I, and III II, III and IV all of these Answer: C Learning Objective: 2.8 Demonstrate the used of curved arrows in drawing resonance structures, stating the two rules to be applied when drawing curved arrows Difficulty: Easy 117. Provide the curved arrow(s) to draw a resonance structure for the following compound. Answer: Learning Objective: 2.8 Demonstrate the used of curved arrows in drawing resonance structures, stating the two rules to be applied when drawing curved arrows Difficulty: Medium 118. Provide the curved arrow(s) to draw a resonance structure for the following compound. Answer: Learning Objective: 2.8 Demonstrate the used of curved arrows in drawing resonance structures, stating the two rules to be applied when drawing curved arrows Difficulty: Medium 119. Provide the curved arrow(s) to draw a resonance structure for the following compound. Answer: Learning Objective: 2.8 Demonstrate the used of curved arrows in drawing resonance structures, stating the two rules to be applied when drawing curved arrows Difficulty: Hard 120. Explain using words as well as structural drawings, if the single curved arrow shown is sufficient to draw the resonance structure. Answer: The single arrow shown will violate the octet rule. Drawing another curved arrow will remove the violation. Learning Objective: 2.8 Demonstrate the used of curved arrows in drawing resonance structures, stating the two rules to be applied when drawing curved arrows Difficulty: Hard 121. Draw the resonance structure indicated by the curved arrows. Answer: Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in resonance structures Difficulty: Medium 122. Draw the resonance structure indicated by the curved arrows. Answer: Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in resonance structures Difficulty: Medium 123. Draw the resonance structure indicated by the curved arrows. Answer: Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in resonance structures Difficulty: Medium 124. Draw the resonance structure indicated by the curved arrows. Answer: Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in resonance structures Difficulty: Medium 125. Draw the curved arrow(s) for converting the first resonance structure into the second resonance structure. Answer: Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in resonance structures Difficulty: Medium 126. Draw the curved arrow(s) for converting the first resonance structure into the second resonance structure. Answer: Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in resonance structures Difficulty: Hard 127. Draw the curved arrow(s) for converting the first resonance structure into the second resonance structure. Answer: Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in resonance structures Difficulty: Hard 128. Draw the curved arrow(s) for converting the first resonance structure into the second resonance structure. Answer: Learning Objective: 2.9 Describe the use of arrow pushing and formal charges in resonance structures Difficulty: Hard 129. Which of the following is a correct resonance structure for compound A? A. B. C. D. E. I II III IV none of these Answer: D Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Easy 130. Which of the following is a correct resonance structure for compound A? A. B. C. D. E. I II III IV None of these Answer: C Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Medium 131. Which of the following is/are correct resonance structure(s) for compound A? A. B. C. D. E. I II and III III and IV I and III I and IV Answer: B Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Easy 132. Which of the following is/are correct resonance structure(s) for compound A? A. B. C. D. I and II II and III III and IV I and III E. I and IV Answer: C Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Medium 133. Which of the following is a correct resonance structure for compound A? A. B. C. D. E. I II III IV none of these Answer: A Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Easy 134. Which of the following is/are correct resonance structure(s) for compound A? A. B. C. D. E. I and II II and III III and IV I, II and III I and IV Answer: D Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Medium 135. Which of the following is a correct resonance structure for compound A? A. B. C. D. E. I II III IV None of these Answer: C Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Easy 136. Which of the following is a correct resonance structure for compound A? A. B. C. D. E. I II III IV None of these Answer: B Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Easy 137. Which of the following is a correct resonance structure for compound A? A. B. C. D. E. I II III IV none of these Answer: A Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Medium 138. Draw resonance structures for the following compound. Answer: Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Medium 139. Draw two resonance structures for HN3. Answer: Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Hard 140. Draw two additional resonance structures for the following compound. Answer: Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Hard 141. Draw two additional resonance structures for the following compound. Answer: Learning Objective: 2.10 Identify resonance structures by naming the five different structural patterns in molecules Difficulty: Hard 142. Which of the following is/are the most significant resonance structure(s)? A. B. C. D. E. I II III II and III all of these Answer: C Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Easy 143. Which of the following is/are the most significant resonance structure(s)? A. B. C. D. E. I II III I and II all of these Answer: B Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Easy 144. Which of the following is/are the most significant resonance structure(s)? A. B. C. D. E. I II III I and II all of these Answer: C Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Medium 145. Which of the following is/are the most significant resonance structure(s)? A. B. C. D. I II III I and II E. I and IV Answer: C Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Medium 146. Which of the following is the most significant resonance structure? A. B. C. D. E. I II III IV None of these Answer: C Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Medium 147. Which of the following is/are the most significant resonance structure(s)? A. B. I II C. D. E. III I and III all of these Answer: B Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Medium 148. Draw significant resonance structures for the following compound, CH3CNO. Which of these is/are the most significant resonance structure(s)? Explain why. Answer: Resonance structure II is most significant, because the more electronegative oxygen atom carries a negative formal charge. Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Hard 149. Draw significant resonance structures for the following compound. Which of these is/are the most significant resonance structure(s)? Explain why. Answer: Resonance structure III is most significant, because all atoms have octet of electrons. Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Hard 150. Draw significant resonance structures for N2O. Which of these is/are the most significant resonance structure(s)? Explain why. Answer: Resonance structure III is most significant, because the more electronegative oxygen atom carries a negative formal charge. Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Hard 151. What is the relationship between the following compounds? A. B. C. D. constitutional isomers resonance structures conformers identical compounds Answer: B Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Easy 152. What is the relationship between the following compounds? A. B. C. D. constitutional isomers resonance structures conformers identical compounds Answer: A Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Easy 153. What is the relationship between the following compounds? A. B. C. D. E. constitutional isomers resonance structures conformers identical compounds different compounds Answer: B Learning Objective: Assessing Importance Section: 2.11 Difficulty: Easy 154. What is the relationship between the following compounds? A. B. C. D. E. constitutional isomers resonance structures conformers identical compounds different compounds Answer: B Learning Objective: 2.11 Distinguish between significant and insignificant resonance structures, describing how the significance of resonance is determined Difficulty: Easy 155. Draw the resonance hybrid of C6H6. Answer: Learning Objective: 2.12 Draw a resonance hybrid using partial bonds and partial charges, reflecting the combination of individual resonance structures Difficulty: Medium 156. Draw the resonance hybrid of CH2CHCHCHCH2+. Answer: Learning Objective: 2.12 Draw a resonance hybrid using partial bonds and partial charges, reflecting the combination of individual resonance structures Difficulty: Medium 157. Draw the resonance hybrid for the following structure. Answer: Learning Objective: 2.12 Draw a resonance hybrid using partial bonds and partial charges, reflecting the combination of individual resonance structures Difficulty: Medium 158. The lone pair on nitrogen in the following compound is _______. A. B. localized delocalized Answer: A Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and describe how delocalized lone pairs participate in resonance and why localized lone pairs do not participate in resonance Difficulty: Easy 159. The lone pair on oxygen in the following compound is _______. A. B. C. both localized both delocalized one localized and one delocalized Answer: C Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and describe how delocalized lone pairs participate in resonance and why localized lone pairs do not participate in resonance Difficulty: Easy 160. The lone pair on nitrogen in the following compound is _______. A. B. localized delocalized Answer: A Learning Objective: 2.12 Distinguish between delocalized and localized lone pairs and describe how delocalized lone pairs participate in resonance and why localized lone pairs do not participate in resonance Difficulty: Easy 161. The lone pairs on oxygen in the following compound are _______. A. B. both localized both delocalized C. one localized and one delocalized Answer: C Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and describe how delocalized lone pairs participate in resonance and why localized lone pairs do not participate in resonance Difficulty: Easy 162. The lone pairs on nitrogen in the following compound are _______. A. B. C. D. three localized three delocalized two localized and one delocalized one localized and two delocalized Answer: A Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and describe how delocalized lone pairs participate in resonance and why localized lone pairs do not participate in resonance Difficulty: Easy 163. For the following compound identify the lone pairs and indicate if each lone pair is localized or delocalized. Answer: Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and describe how delocalized lone pairs participate in resonance and why localized lone pairs do not participate in resonance Difficulty: Medium 164. For the following compound identify the lone pairs and indicate if each lone pair is localized or delocalized. Answer: Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and describe how delocalized lone pairs participate in resonance and why localized lone pairs do not participate in resonance Difficulty: Medium 165. For the following compound identify the lone pairs and indicate if each lone pair is localized or delocalized. Answer: Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and describe how delocalized lone pairs participate in resonance and why localized lone pairs do not participate in resonance Difficulty: Medium 166. For the following compound what is the hybridization state and molecular geometry at each oxygen and nitrogen atom. Answer: Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and describe how delocalized lone pairs participate in resonance and why localized lone pairs do not participate in resonance Difficulty: Hard 167. Caffeine has the following structure. What is the hybridization state and molecular geometry at each nitrogen atom in caffeine? Answer: Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and describe how delocalized lone pairs participate in resonance and why localized lone pairs do not participate in resonance Difficulty: Hard 168. Enalapril, is a drug used in the treatment of heart disease. What is the hybridization state and molecular geometry at the indicated atoms in Enalapril? Answer: Learning Objective: 2.13 Distinguish between delocalized and localized lone pairs and describe how delocalized lone pairs participate in resonance and why localized lone pairs do not participate in resonance Difficulty: Hard