Organic Chemistry, 2nd Edition Test Bank

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Chapter Two Topic: Molecular Representation Section: 2.1 Difficulty Level: Easy 1. What is the molecular formula for the following compound? H H H C C H H O H H C C H H H A) C2H6O B) C4H6O C) C4H10O D) C2H4O E) None of these Ans: C Topic: Molecular Representation Section: 2.1 Difficulty Level: Easy 2. Which of the following compounds have a molecular formula of C2H6O? CH3OCH3 CH3CH2OCH3 CH3CH2OH I II III A) I B) II C) III D) IV E) Both I & III Ans: E Topic: Molecular Representation Section: 2.1 Difficulty Level: Easy CH3CHOHCH3 IV 3. Which of the following is the correct condensed structure for the following compound? H H H C H C H H C H O C H H H A) CH3CH3CH2OH B) CH3CH2CH2OH C) (CH3)2CHCH2OH D) CH3CH2CH2OCH3 E) CH3C2H3CH3OH Ans: C Topic: Molecular Representation Section: 2.1 Difficulty Level: Easy 4. Which of the following is the correct condensed structure for the following compound? H H H H H Cl H C C C C C C H O H H H H H A) CH3CHOHCH2CHClCH3 B) CH3CHOH(CH2)2CHClCH3 C) (CH3)2CHOHCH2CH2Cl D) CH3CHCH2CH2OHCH3CHCl E) CH3C2H4CH3OHCl Ans: B Topic: Molecular Representation Section: 2.1 Difficulty Level: Medium H 5. Which of the following is the correct condensed structure for the following compound? A) CH2=CH(CH2)3C(CH3)3 B) CH(CH2)4C(CH3)3 C) (CH3)2CH(CH2)4CH3 D) CH2CH(CH2)3C(CH3)3 E) (CH)3(CH2)3C(CH3)3 Ans: A Topic: Molecular Representation Section: 2.1 Difficulty Level: Medium 6. Which of the following is the correct condensed structure for the following compound? H H H C H C C H H H H H C H C C C C C H H H C H A) CH3C2(CH2)3C(CH3)3 B) CH3CC(CH2)3C(CH3)2CH3 C) (CH3)3C2(CH2)3CH3 D) CH3C๏‚บC(CH2)3C(CH3)3 E) CH3CC(CH2)3C(CH3)3 Ans: D Topic: Molecular Representation Section: 2.1 Difficulty Level: Medium H H H H 7. Which of the following is the correct condensed structure for the following compound? H H H H H H H H C H H H C H C C C C C C C H C H H Br H H H H H H A) CH3C(CH3)2(CH2)2(CH)BrC(CH3)2 B) CH3CH3CH3C(CH2)2C(CH3)2CHBr C) (CH3)3C(CH2)3BrCHCH3CH3 D) CH3CH3CH3C(CH2)2CHBrCHCH3CH3 E) (CH3)3C(CH2)2CHBrCH(CH3)2 Ans: E Topic: Molecular Representation Section: 2.1 Difficulty Level: Hard 8. Provide correct condensed structure for the following compound. H H H H H H H H C H H C C C C H C H H H H O H C H C H H C C C H H H H H Ans: (CH3)3C(CH2)2OCH(CH2CH3)2 Topic: Molecular Representation Section: 2.1 Difficulty Level: Hard 9. Provide correct condensed structure for the following compound. H H H H H H H H C H C N C C C C C H C H H H H H H H H Ans: (CH3)2N(CH2)3CH(CH3)2 Topic: Molecular Representation Section: 2.1 Difficulty Level: Easy H 10. Which of the following is the correct molecular formula for (CH3CH2)4C? A) C8H20 B) C5H20 C) C9H20 D) C6H5 E) C3H20 Ans: C Topic: Molecular Representation Section: 2.1 Difficulty Level: Easy 11. Which of the following is the correct Lewis structure for CH3(CH2)2NH2? H H H C C N H H H H H H H H C C C N H H H H I H H H H H C C C N H H H H H CH3CH2CH2NH2 IV III II A) I B) II C) III D) IV E) Both II & III Ans: C Topic: Molecular Representation Section: 2.1 Difficulty Level: Easy 12. Which of the following is the correct Lewis structure for CH3(CH2)2OH? H H H C C H H O H H H H H C C C H H H I A) I B) II C) III D) IV E) Both II & III Ans: B Topic: Molecular Representation Section: 2.1 Difficulty Level: Easy II O H H H H H C C C H H H III O H CH3CH2CH2OH IV 13. Which of the following is the correct Lewis structure for (CH3)2CHCH2OH? H H H H H C C C C H H H H H H H C H H O H H H H H H C C C C H H H H O H H C H C H H O H H C H C C H H IV III II I C H H H H C H A) I B) II C) III D) IV E) Both III & IV Ans: C Topic: Molecular Representation Section: 2.1 Difficulty Level: Medium 14. Which of the following is the correct Lewis structure for (CH3)3C(CH2)2NHCH3? H H H H H H C H C C C C N C H C H H H H H H H H H H H HH H C H H H C C C C C N H H C H H H H I H H H H H HH H C H H H C C C C N C H C H H H H H HH IV A) I B) II C) III D) IV E) V Ans: D Topic: Molecular Representation Section: 2.1 Difficulty Level: Medium H H H H C H C C C C N H C H H H H H H III H H H H H C C C C C N C H H C H H H H H HH V H H II H H H H CH3 OH 15. Draw the Lewis structure for CH3C๏‚บC(CH2)3C(CH3)3. H Ans: H H H H C C C H H H H C H C C C C C H H H C H H H H H Topic: Molecular Representation Section: 2.1 Difficulty Level: Hard 16. Draw the Lewis structure for (CH3)3C(CH2)2OCH(CH2CH3)2. H Ans: H H H H H H H H C H H C C C C H C H H H H O C H C H H C C C H H H H H Topic: Bond Line Structure Section: 2.2 Difficulty Level: Easy 17. Which of the following bond-line structures are of the same compound? I A) I & II B) II & III C) III & IV D) II & IV E) None of these Ans: D Topic: Bond Line Structure Section: 2.2 Difficulty Level: Easy II III IV 18. Which of the following bond-line structures are of the same compound? I II III A) I & III B) II & III C) III & IV D) II & IV E) None of these Ans: A Topic: Bond Line Structure Section: 2.2 Difficulty Level: Easy 19. How many H atoms are connected to the indicated carbon atom? A) one B) two C) three D) four E) none Ans: E Topic: Bond Line Structure Section: 2.2 Difficulty Level: Easy 20. How many H atoms are connected to the indicated carbon atom? A) one B) two C) three D) four E) none Ans: A Topic: Bond Line Structure Section: 2.2 Difficulty Level: Easy IV 21. How many H atoms are connected to the indicated carbon atom? A) one B) two C) three D) four E) none Ans: B Topic: Bond Line Structure Section: 2.2 Difficulty Level: Easy 22. How many H atoms are connected to the indicated carbon atom? A) one B) two C) three D) four E) none Ans: A Topic: Bond Line Structure Section: 2.2 Difficulty Level: Easy 23. How many H atoms are connected to the indicated carbon atom? A) one B) two C) three D) four E) none Ans: E Topic: Bond Line Structure Section: 2.2 Difficulty Level: Easy 24. For the following transformation how many H atoms are added or lost? A) Added one B) Added two C) Lost one D) Lost two E) No change Ans: D Topic: Bond Line Structure Section: 2.2 Difficulty Level: Easy 25. For the following transformation how many H atoms are added or lost? O OH A) Added one B) Added two C) Lost one D) Lost two E) No change Ans: B Topic: Bond Line Structure Section: 2.2 Difficulty Level: Easy 26. For the following transformation how many H atoms are added or lost? A) Added one B) Added two C) Lost one D) Lost two E) No change Ans: E Topic: Bond Line Structure Section: 2.2 Difficulty Level: Easy 27. For the following transformation how many H atoms are added or lost? OH O O A) Added one B) Added two C) Lost one D) Lost two E) No change Ans: E Topic: Bond Line Structure Section: 2.2 Difficulty Level: Medium 28. For the following transformation how many H atoms are added or lost? OH A) Added one B) Added two C) Lost one D) Lost two E) No change Ans: D Topic: Bond Line Structure Section: 2.2 Difficulty Level: Medium 29. For the following transformation how many H atoms are added or lost? A) Added one B) Added two C) Lost one D) Lost two E) No change Ans: E Topic: Bond Line Structure Section: 2.2 Difficulty Level: Easy 30. Which of the following is the correct Lewis structure for the following compound? O H H C H O C H C H H I II A) I B) II C) III D) IV E) None of these Ans: B Topic: Bond Line Structure Section: 2.2 Difficulty Level: Easy H O C H H O C H C O H III H O C C H H IV H 31. Which of the following is the correct bond-line structure for (CH3)4C? I IV III II A) I B) II C) III D) IV E) None of these Ans: C Topic: Bond Line Structure Section: 2.2 Difficulty Level: Easy 32. Which of the following is the correct bond-line structure for (CH3)2CHCH2CH3? I IV III II A) I B) II C) III D) IV E) None of these Ans: A Topic: Bond Line Structure Section: 2.2 Difficulty Level: Medium 33. Which of the following is the correct bond-line structure for (CH3)2CHCH2C(CH3)3? I A) I B) II C) III D) IV E) None of these Ans: B Topic: Bond Line Structure Section: 2.2 II III IV Difficulty Level: Medium 34. Which of the following is the correct bond-line structure for CH3C๏‚บC(CH2)2CH(CH3)2? I III II IV A) I B) II C) III D) IV E) None of these Ans: D Topic: Bond Line Structure Section: 2.2 Difficulty Level: Medium 35. Which of the following is the correct bond-line structure for CH3CHOH(CH2)2CH(CH2CH3)2? OH OH O O O I II III A) I B) II C) III D) IV E) V Ans: B Topic: Bond Line Structure Section: 2.2 Difficulty Level: Medium 36. Draw a bond-line structure for CH3CH2O(CH2)2CH(CH3)2. Ans: O Topic: Bond Line Structure Section: 2.2 Difficulty Level: Hard IV V 37. Draw a bond-line structure for (CH3)2N(CH2)3CH(CH3)2. Ans: N Topic: Bond Line Structure Section: 2.2 Difficulty Level: Hard 38. Draw a bond-line structure for CH3C๏‚บC(CH2)3C(CH3)2CH2OCH3. Ans: O Topic: Bond Line Structure Section: 2.2 Difficulty Level: Hard 39. Draw a bond-line structure for each constitutional isomer with a molecular formula of C2H4O. H Ans: O O O Topic: Bond Line Structure Section: 2.2 Difficulty Level: Hard 40. Draw a bond-line structure for each constitutional isomer with a molecular formula of C3H8O. Ans: OH OH Topic: Bond Line Structure Section: 2.2 Difficulty Level: Hard O 41. Provide a condensed structure for the following compound. Ans: (CH3)3CCH2CH(CH2CH3)(CH2)2CH(CH3)CH2CH3 Topic: Bond Line Structure Section: 2.2 Difficulty Level: Hard 42. Provide a condensed structure for the following compound. NH2 Ans: (CH3)3C(CH2)2CH(NH2)CH=CHCH3 Topic: Bond Line Structure Section: 2.2 Difficulty Level: Hard 43. Draw a bond-line structure for each constitutional isomer with molecular formula C4H10O. Ans: OH OH OH OH O O Topic: Bond Line Structure Section: 2.2 Difficulty Level: Hard O 44. Draw a bond-line structure for each constitutional isomer with molecular formula C4H11N. Ans: NH2 NH2 NH2 NH2 H N N N H N H Topic: Bond Line Structure Section: 2.2 Difficulty Level: Medium 45. Naproxen, sold under the trade name Aleve, has the following structure. What is the molecular formula for naproxen? OH O O Ans: C14H14O3 Topic: Bond Line Structure Section: 2.2 Difficulty Level: Hard 46. AZT, used in the treatment of AIDS, has the following structure. What is the molecular formula for AZT? O O N HO NH O N3 Ans: C10H13N5O4 Topic: Bond Line Structure Section: 2.2 Difficulty Level: Hard 47. Capsaicin, found in peppers, has the following structure. What is the molecular formula for capsaicin? H N O O OH Ans: C18H27NO3 Topic: Identifying Functional Groups Section: 2.3 Difficulty Level: Easy 48. Which of the following compounds contain an alcohol functional group? NH2 O OH I II IV III A) I B) II C) III D) IV E) None of these Ans: C Topic: Identifying Functional Groups Section: 2.3 Difficulty Level: Easy 49. Which of the following compounds contain an alkene functional group? NH2 I II A) I B) II C) III D) IV E) None of these Ans: A Topic: Identifying Functional Groups Section: 2.3 III IV Difficulty Level: Easy 50. Which of the following compounds contain an amine functional group? NH2 O OH I II IV III A) I B) II C) III D) IV E) None of these Ans: D Topic: Identifying Functional Groups Section: 2.3 Difficulty Level: Easy 51. Which of the following compounds contain a ketone functional group? O O O O HO O I II A) I B) II C) III D) IV E) All of these Ans: A Topic: Identifying Functional Groups Section: 2.3 Difficulty Level: Easy III IV 52. Which of the following compounds contain an aromatic ring? O I II III IV A) I B) II C) III D) IV E) Both III & IV Ans: C Topic: Identifying Functional Groups Section: 2.3 Difficulty Level: Easy 53. Which of the following compounds contain an ester functional group? O O N N O I II O IV III A) I B) II C) III D) IV E) Both I & IV Ans: A Topic: Identifying Functional Groups Section: 2.3 Difficulty Level: Easy 54. Which of the following compounds contain an amide functional group? O O N N N O I II A) I B) II C) III D) IV E) Both II & III Ans: B Topic: Identifying Functional Groups Section: 2.3 C III IV Difficulty Level: Medium 55. What functional group(s) is (are) present in the following compound? O A) ketone & alkene B) ketone & alkyne C) aldehyde & alkene D) aldehyde & alkyne E) ester & alkene Ans: C Topic: Identifying Functional Groups Section: 2.3 Difficulty Level: Medium 56. Which of the following compounds have both a ketone and an ester functional group? O O O O I II A) I B) II C) III D) IV E) V Ans: E Topic: Identifying Functional Groups Section: 2.3 Difficulty Level: Medium OH O O O O O O III OH IV OH V O 57. Norethynodrel, a component of the first combined oral contraceptive, has the following structure. Identify the functional groups in Norethynodrel. OH O alcohol Ans: OH alkyne ketone O alkene Topic: Identifying Functional Groups Section: 2.3 Difficulty Level: Medium 58. Identify the functional groups in the following compound. OH S N O Ans: OH alcohol S N O amide Topic: Identifying Functional Groups Section: 2.3 Difficulty Level: Hard sulfide 59. Tamifluยฎ, is the most effective antiviral drug used to treat avian influenza, has the following structure. Identify the functional groups in Tamifluยฎ. O O O O N H NH2 alkene Ans: O ether O O O ester N H NH2 amide amine Topic: Identifying Functional Groups Section: 2.3 Difficulty Level: Hard 60. Aspartame, an artificial sweetener used in Equalยฎ and diet beverages, has the following structure. Identify the functional groups in Aspartame. NH2 O H N OH O O O Ans: amine aromatic amide NH2 O H N OH O O ester Topic: Identifying Functional Groups Section: 2.3 Difficulty Level: Hard O carboxylic acid 61. Draw all the constitutional isomers with a molecular formula of C3H6O and label the functional groups in each isomer. Ans: Topic: Identifying Functional Groups Section: 2.3 Difficulty Level: Hard 62. Amoxicillin, an antibiotic, has the following structure. Identify the functional groups in amoxicillin. NH2 H N S O HO N O O HO Ans: aromatic amine NH2 amide sulfide H N phenol S HO O N O amide O HO carboxylic acid Topic: Identifying Functional Groups Section: 2.3 Difficulty Level: Hard 63. Viracept, used in the treatment of HIV, has the following structure. Identify the functional groups in Viracept. H S O N O HO N N H OH aromatic Ans: H sulfide S phenol O N O HO N amide H N amide OH amine aromatic alcohol Topic: Carbon Atoms with Formal Charges Section: 2.4 Difficulty Level: Easy 64. What is the formal charge on the oxygen atom in the following compound? O A) +1 B) +2 C) -1 D) -2 E) 0 Ans: A Topic: Carbon Atoms with Formal Charges Section: 2.4 Difficulty Level: Easy 65. What is the formal charge on the nitrogen atom in the following compound? N A) -1 B) -2 C) +1 D) +2 E) 0 Ans: C Topic: Carbon Atoms with Formal Charges Section: 2.4 Difficulty Level: Easy 66. What is the formal charge on the nitrogen atom in the following compound? N A) +1 B) +2 C) -1 D) -2 E) 0 Ans: A Topic: Carbon Atoms with Formal Charges Section: 2.4 Difficulty Level: Easy 67. What is the formal charge on the indicated oxygen atom in the following compound? O O A) +1 B) +2 C) -1 D) -2 E) 0 Ans: E Topic: Carbon Atoms with Formal Charges Section: 2.4 Difficulty Level: Easy 68. What is the formal charge on the nitrogen atom in the following compound? N A) +1 B) +2 C) -1 D) -2 E) 0 Ans: E Topic: Carbon Atoms with Formal Charges Section: 2.4 Difficulty Level: Medium 69. Which of the following compounds have +1 as a formal charge on an oxygen atom? O O O N N O I O II A) I B) II C) III D) IV E) Both I & IV Ans: B Topic: Carbon Atoms with Formal Charges Section: 2.4 Difficulty Level: Medium III IV 70. Which of the following compounds have +1 as a formal charge on the nitrogen atom? O O N N I N II III N IV A) I B) II C) III D) IV E) Both I & II Ans: D Topic: Carbon Atoms with Formal Charges Section: 2.4 Difficulty Level: Medium 71. Determine the formal charges on each atom except hydrogen. H H C S C N H H Ans: H 0 C +1 0 -1 S C N H Topic: Carbon Atoms with Formal Charges Section: 2.4 Difficulty Level: Hard 72. Diazomethane has the molecular formula CH2N2. Draw the preferred Lewis structure for diazomethane and assign formal charges to all atoms, if any. -1 +1 0 Ans: H C N N H Topic: Carbon Atoms with Formal Charges Section: 2.4 Difficulty Level: Easy 73. How many hydrogen atoms are connected to the indicated carbon atom? A) one B) two C) three D) four E) none Ans: A Topic: Carbon Atoms with Formal Charges Section: 2.4 Difficulty Level: Easy 74. How many hydrogen atoms are connected to the indicated carbon atom? A) one B) two C) three D) four E) none Ans: E Topic: Carbon Atoms with Formal Charges Section: 2.4 Difficulty Level: Easy 75. How many hydrogen atoms are connected to the indicated carbon atom? A) one B) two C) three D) four E) none Ans: A Topic: Carbon Atoms with Formal Charges Section: 2.4 Difficulty Level: Easy 76. How many hydrogen atoms are connected to the indicated carbon atom? A) one B) two C) three D) four E) none Ans: A Topic: Carbon Atoms with Formal Charges Section: 2.4 Difficulty Level: Easy 77. How many hydrogen atoms are connected to the indicated carbon atom? A) one B) two C) three D) four E) none Ans: E Topic: Carbon Atoms with Formal Charges Section: 2.4 Difficulty Level: Easy 78. How many hydrogen atoms are connected to the indicated carbon atom? A) one B) two C) three D) four E) none Ans: A Topic: Carbon Atoms with Formal Charges Section: 2.4 Difficulty Level: Medium 79. Draw Lewis structure for the following compound. O Ans: O H H C H H C C C C C H H H H H H Topic: Identifying lone pairs Section: 2.5 Difficulty Level: Easy 80. How many lone pairs of electrons are on the oxygen atom? O A) one B) two C) three D) four E) none Ans: C Topic: Identifying lone pairs Section: 2.5 Difficulty Level: Easy 81. How many lone pairs of electrons are on the nitrogen atom? N A) one B) two C) three D) four E) none Ans: B Topic: Identifying lone pairs Section: 2.5 Difficulty Level: Easy 82. How many lone pairs of electrons are on the oxygen atom? O N A) one B) two C) three D) four E) none Ans: B Topic: Identifying lone pairs Section: 2.5 Difficulty Level: Easy 83. How many lone pairs of electrons are on the nitrogen atom? O N A) one B) two C) three D) four E) none Ans: A Topic: Identifying lone pairs Section: 2.5 Difficulty Level: Easy 84. How many lone pairs of electrons are on the nitrogen atom? N A) one B) two C) three D) four E) none Ans: E Topic: Identifying lone pairs Section: 2.5 Difficulty Level: Easy 85. How many lone pairs of electrons are on the indicated oxygen atom? O O A) one B) two C) three D) four E) none Ans: B Topic: Identifying lone pairs Section: 2.5 Difficulty Level: Easy 86. How many lone pairs of electrons are on the indicated oxygen atom? O O A) one B) two C) three D) four E) none Ans: A Topic: Identifying lone pairs Section: 2.5 Difficulty Level: Medium 87. How many total lone pairs of electrons are on both oxygen atoms in the following compound? H2O O A) one B) two C) three D) four E) none Ans: C Topic: Identifying lone pairs Section: 2.5 Difficulty Level: Medium 88. Draw all lone pairs of electrons for the following compound. O H3 N O OH Ans: O H3 N O OH Topic: Identifying lone pairs Section: 2.5 Difficulty Level: Medium 89. Draw all lone pairs of electrons for the following compound. OH C N O Ans: OH C N O Topic: Three-Dimensional Bond-Line Structures Section: 2.6 Difficulty Level: Easy 90. The indicated bond in the following compound is_____ of the paper. A) in the plane B) out of the plane C) behind the plane D) None of these Ans: B Topic: Three-Dimensional Bond-Line Structures Section: 2.6 Difficulty Level: Easy 91. The indicated bond in the following compound is_____ of the paper. OH OH OH A) in the plane B) out of the plane C) behind the plane D) None of these Ans: C Topic: Three-Dimensional Bond-Line Structures Section: 2.6 Difficulty Level: Easy 92. The indicated bond in the following compound is_____ of the paper. O A) in the plane B) out of the plane C) behind the plane D) None of these Ans: C Topic: Three-Dimensional Bond-Line Structures Section: 2.6 Difficulty Level: Easy 93. Which of the following is a Fischer projection? O H C OH OH H OH H OH H OH H OH H OH OH OH H I II CH2OH A) I B) II C) III D) IV E) Both III & IV Ans: B Topic: Three-Dimensional Bond-Line Structures Section: 2.6 Difficulty Level: Easy III IV 94. Which of the following is a Haworth projection? O H C OH OH H OH H OH H OH H OH H OH OH OH H I II III IV CH2OH A) I B) II C) III D) IV E) Both III & IV Ans: C Topic: Three-Dimensional Bond-Line Structures Section: 2.6 Difficulty Level: Medium 95. For the following compound label the bonds that are out of the plane and behind the plane of the paper. HO O O OH HO OH HO Ans: O out of the plane O OH HO OH behind the plane Topic: Introduction to Resonance Section: 2.7 Difficulty Level: Easy 96. Which of the following pairs are resonance structures of each other? I. II. O III. O IV. N N A) I B) II C) III D) IV E) None of these Ans: D Topic: Introduction to Resonance Section: 2.7 Difficulty Level: Easy 97. Which of the following pairs are resonance structures of each other? I. II. O III. O IV. N A) I B) II C) III D) IV E) None of these Ans: C Topic: Introduction to Resonance Section: 2.7 Difficulty Level: Easy N 98. Spreading of positive or negative charge over two or more atoms in a compound is called_______. A) isomerism B) delocalization C) stereoisomerism D) localization E) None of these Ans: B Topic: Introduction to Resonance Section: 2.7 Difficulty Level: Easy 99. Delocalization of charge over two or more atoms _______ a molecule. A) destabilizes B) delocalizes C) localizes D) stabilizes E) None of these Ans: D Topic: Introduction to Resonance Section: 2.7 Difficulty Level: Medium 100. Resonance structures have _______ connectivity of atoms and _______ distribution of electrons. A) different, same B) same, same C) different, different D) same, different E) None of these Ans: D Topic: Introduction to Resonance Section: 2.7 Difficulty Level: Medium 101. What is a resonance hybrid? Ans: A molecule that can be represented by drawing two or more resonance structures is viewed as resonance hybrid. Topic: Curved Arrows Section: 2.8 Difficulty Level: Easy 102. Which of the following violates the rules for curved arrows? O OH O O II I III A) I B) II C) III D) IV E) None of these Ans: A Topic: Curved Arrows Section: 2.8 Difficulty Level: Easy 103. Which of the following violates the rules for curved arrows? N H H H H H H N C O C I II III IV A) I B) II & IV C) I & III D) III & IV E) None of these Ans: C Topic: Curved Arrows Section: 2.8 Difficulty Level: Easy IV 104. Which of the following violates the rules for curved arrows? N II I O O III IV A) I & II B) III & IV C) I, II & III D) II, III & IV E) All of these Ans: C Topic: Curved Arrows Section: 2.8 Difficulty Level: Medium 105. Provide the curved arrow(s) to draw a resonance structure for the following compound. O Ans: O Topic: Curved Arrows Section: 2.8 Difficulty Level: Medium 106. Provide the curved arrow(s) to draw a resonance structure for the following compound. Ans: Topic: Curved Arrows Section: 2.8 Difficulty Level: Hard 107. Provide the curved arrow(s) to draw a resonance structure for the following compound. O O Ans: O O Topic: Curved Arrows Section: 2.8 Difficulty Level: Hard 108. Explain using words as well as structural drawings, if the single curved arrow shown is sufficient to draw the resonance structure. O O Ans: The single arrow shown will violate the octet rule. Drawing another curved arrow will remove the violation. O O Topic: Formal Charges in Resonance Structures Section: 2.9 Difficulty Level: Easy 109. Which of the following is a correct resonance structure for compound A? N NH NH NH N A I II III IV A) I B) II C) III D) IV E) none of these Ans: D Topic: Formal Charges in Resonance Structures Section: 2.9 Difficulty Level: Easy 110. Which of the following is a correct resonance structure for compound A? A I II III IV A) I B) II C) III D) IV E) None of these Ans: C Topic: Formal Charges in Resonance Structures Section: 2.9 Difficulty Level: Medium 111. Which of the following is/are correct resonance structure(s) for compound A? O A O I II A) I B) II & III C) III & IV D) I & III E) I & IV Ans: B Topic: Formal Charges in Resonance Structures O O O III IV Section: 2.9 Difficulty Level: Medium 112. Which of the following is/are correct resonance structure(s) for compound A N N N N A III II I N IV A) I & II B) II & III C) III & IV D) I & III E) I & IV Ans: C Topic: Formal Charges in Resonance Structures Section: 2.9 Difficulty Level: Medium 113. Which of the following is/are correct resonance structure(s) for compound A? O A O I O II O III A) I & II B) II & III C) III & IV D) I, II & III E) I & IV Ans: D Topic: Formal Charges in Resonance Structures Section: 2.9 Difficulty Level: Easy 114. Draw the resonance structure indicated by the curved arrows. O Ans: O Topic: Formal Charges in Resonance Structures Section: 2.9 O IV Difficulty Level: Easy 115. Draw the resonance structure indicated by the curved arrows. Ans: Topic: Formal Charges in Resonance Structures Section: 2.9 Difficulty Level: Medium 116. Draw the resonance structure indicated by the curved arrows. NH2 Ans: NH2 Topic: Formal Charges in Resonance Structures Section: 2.9 Difficulty Level: Medium 117. Draw the resonance structure indicated by the curved arrows. OH Ans: OH Topic: Formal Charges in Resonance Structures Section: 2.9 Difficulty Level: Medium 118. Draw the curved arrow(s) for converting the first resonance structure into the second resonance structure. O O Ans: O O Topic: Formal Charges in Resonance Structures Section: 2.9 Difficulty Level: Medium 119. Draw the curved arrow(s) for converting the first resonance structure into the second resonance structure. Ans: Topic: Formal Charges in Resonance Structures Section: 2.9 Difficulty Level: Hard 120. Draw the curved arrow(s) for converting the first resonance structure into the second resonance structure. O O O O Ans: O O O O Topic: Formal Charges in Resonance Structures Section: 2.9 Difficulty Level: Hard 121. Draw the curved arrow(s) for converting the first resonance structure into the second resonance structure. O O Ans: O Topic: Formal Charges in Resonance Structures Section: 2.9 Difficulty Level: Hard O 122. Explain using words as well as structural drawings, if the single curved arrow shown is sufficient for the following resonance structures? O O O O Ans: The single arrow shown will violate the octet rule. Drawing another curved arrow will remove the violation. O O O O Topic: Pattern Recognition Section: 2.10 Difficulty Level: Easy 123. Which of the following is a correct resonance structure for compound A O O O O A A) I B) II C) III D) IV E) None of these Ans: A Topic: Pattern Recognition Section: 2.10 Difficulty Level: Easy OH O O I O II O III IV 124. Which of the following is a correct resonance structure for compound A? Cl A Cl Cl II I Cl Cl III IV A) I B) II C) III D) IV E) None of these Ans: C Topic: Pattern Recognition Section: 2.10 Difficulty Level: Easy 125. Which of the following is a correct resonance structure for compound A? N N N N N A I II III IV A) I B) II C) III D) IV E) None of these Ans: B Topic: Pattern Recognition Section: 2.10 Difficulty Level: Easy 126. Which of the following is a correct resonance structure for compound A? A A) I B) II C) III D) IV E) None of these Ans: A Topic: Pattern Recognition I II III IV Section: 2.10 Difficulty Level: Medium 127. Draw resonance structures for the following compound. O Ans: O O O O Topic: Pattern Recognition Section: 2.10 Difficulty Level: Hard 128. Draw two additional resonance structures for the following compound. Ans: Topic: Pattern Recognition Section: 2.10 Difficulty Level: Hard 129. Draw two additional resonance structures for the following compound. N Ans: N O N N Topic: Pattern Recognition Section: 2.10 Difficulty Level: Hard O N N O N N O 130. Draw two additional resonance structures for the following compound. N Ans: C N N N Topic: Assessing Importance Section: 2.11 Difficulty Level: Easy 131. Which of the following is/are the most significant resonance structure(s)? H N H N H N I III II A) I B) II C) III D) II & III E) all of these Ans: C Topic: Assessing Importance Section: 2.11 Difficulty Level: Easy 132. Which of the following is/are the most significant resonance structure(s)? O O I A) I B) II C) III D) I & II E) all of these Ans: B Topic: Assessing Importance Section: 2.11 Difficulty Level: Easy II O III 133. Which of the following is/are the most significant resonance structure(s)? C N I N II N III A) I B) II C) III D) I & II E) all of these Ans: C Topic: Assessing Importance Section: 2.11 Difficulty Level: Medium 134. Which of the following is/are the most significant resonance structure(s)? O O I O II O III IV A) I B) II C) III D) I & II E) I & IV Ans: C Topic: Assessing Importance Section: 2.11 Difficulty Level: Medium 135. Which of the following is the most significant resonance structure? H2C N N I A) I B) II C) III D) IV E) None of these Ans: C Topic: Assessing Importance Section: 2.11 Difficulty Level: Medium H2C N II N H2C N III N H2C N IV N 136. Which of the following is/are the most significant resonance structure(s)? N N I II N III A) I B) II C) III D) I & III E) all of these Ans: B Topic: Assessing Importance Section: 2.11 Difficulty Level: Hard 137. Draw significant resonance structures for the following compound. Which of this is/are most significant resonance structure(s)? Explain why. H H C C N O H H Ans: H H C C H I N O H C H H C N O H C C O III H II N Resonance structure III is most significant, because the more electronegative oxygen atom carries a negative formal charge. Topic: Assessing Importance Section: 2.11 Difficulty Level: Hard 138. Draw significant resonance structures for the following compound. Which of this is/are most significant resonance structure(s)? Explain why. O Ans: O I O II O III O IV Resonance structure III is most significant, because all atoms have octet of electrons. Topic: Assessing Importance Section: 2.11 Difficulty Level: Hard 139. Draw significant resonance structures for the following compound. Which of this is/are most significant resonance structure(s)? Explain why. Ans: Resonance structure I is most significant, because the more electronegative oxygen atom carries a negative formal charge. Topic: Assessing Importance Section: 2.11 Difficulty Level: Easy 140. What is the relationship between the following compounds? H O N O H O N O A) Constitutional isomers B) Resonance structures C) conformers D) Identical compounds Ans: B Topic: Assessing Importance Section: 2.11 Difficulty Level: Easy 141. What is the relationship between the following compounds? O A) Constitutional isomers B) Resonance structures C) conformers D) Identical compounds E) Different compounds Ans: A Topic: Assessing Importance Section: 2.11 Difficulty Level: Easy O 142. What is the relationship between the following compounds? O O A) Constitutional isomers B) Resonance structures C) conformers D) Identical compounds E) Different compounds Ans: B Topic: Assessing Importance Section: 2.11 Difficulty Level: Easy 143. What is the relationship between the following compounds? A) Constitutional isomers B) Resonance structures C) conformers D) Identical compounds E) Different compounds Ans: B Topic: Delocalized and Localized Lone Pairs Section: 2.12 Difficulty Level: Easy 144. The lone pair on nitrogen in the following compound is _______. N A) localized B) delocalized Ans: A Topic: Delocalized and Localized Lone Pairs Section: 2.12 Difficulty Level: Easy 145. The lone pair on oxygen in the following compound is _______. O A) localized B) delocalized Ans: B Topic: Delocalized and Localized Lone Pairs Section: 2.12 Difficulty Level: Easy 146. The lone pair on nitrogen in the following compound is _______. O N A) localized B) delocalized Ans: A Topic: Delocalized and Localized Lone Pairs Section: 2.12 Difficulty Level: Easy 147. The lone pairs on oxygen in the following compound are _______. O N A) both localized B) both delocalized C) one localized D) one delocalized E) Both C & D Ans: E Topic: Delocalized and Localized Lone Pairs Section: 2.12 Difficulty Level: Easy 148. The lone pair on nitrogen in the following compound is _______. N N N A) localized B) delocalized Ans: A Topic: Delocalized and Localized Lone Pairs Section: 2.12 Difficulty Level: Medium 149. For the following compound identify the lone pairs and indicate if each lone pair is localized or delocalized. N H2N O localized Ans: N delocalized H2N O localized delocalized Topic: Delocalized and Localized Lone Pairs Section: 2.12 Difficulty Level: Medium 150. For the following compound identify the lone pairs and indicate if each lone pair is localized or delocalized. O N O Ans: localized O delocalized N O localized Topic: Delocalized and Localized Lone Pairs Section: 2.12 Difficulty Level: Medium 151. For the following compound identify the lone pairs and indicate if each lone pair is localized or delocalized. OH O H N Ans: delocalized localized OH O H N delocalized localized Topic: Delocalized and Localized Lone Pairs Section: 2.12 Difficulty Level: Hard 152. For the following compound what is the hybridization state and molecular geometry at each oxygen and nitrogen atom OH O H N sp2, bent Ans: sp2, bent OH O H N Topic: Delocalized and Localized Lone Pairs Section: 2.12 Difficulty Level: Hard sp2, trigonal planar 153. Caffeine has the following structure. What is the hybridization state and molecular geometry at each nitrogen atom in Caffeine? O N N O N N Ans: O sp2, trigonal planar 2 sp , trigonal planar N N O N N sp2, bent sp2, trigonal planar Topic: Delocalized and Localized Lone Pairs Section: 2.12 Difficulty Level: Hard 154. 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? O O N N O HO H O Ans: sp2, bent sp2, trigonal planar O O N sp2, bent N O HO O H sp3, trigonal pyramidal

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