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Test Bank for Organic Chemistry 1st Edition by Klein Chapter 7 Topic: Introduction to Substitution Section 1 Difficulty Level: Easy 1. Which of the following is a substitution reaction? Ans: C Chapter 7 Topic: Introduction to Substitution Section 1 Difficulty Level: Easy 2. Which of the following is a substitution reaction? Ans: D Chapter 7 Topic: Introduction to Substitution Section 1 Difficulty Level: Easy 3. Which of the following is a substitution reaction? Ans: B Topic: Introduction to Substitution Section 1 Difficulty Level: Medium
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5. Draw an example of a substitution reaction. Ans: Numerous options! Topic: Introduction to Substitution Section 1 Difficulty Level: Easy 6. What is the nucleophile in the following reaction? Ans: B Topic: Introduction to Substitution Section 1 Difficulty Level: Easy 7. What is the electrophile in the following reaction? Ans: A Topic: Introduction to Substitution Section 1 Difficulty Level: Easy 8. What is the leaving group in the following reaction? carbon bromide hydrogen nitrogen Ans: B Topic: Introduction to Substitution Section 1 Difficulty Level: Hard
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9. What are two features typical of a leaving group? Ans: 1. A leaving group withdraws electron density from the adjacent carbon, and 2. A leaving group can stabilize negative charge. Topic: Introduction to Substitution Section 1 Difficulty Level: Medium 10. For the following reaction, label the nucleophile, electrophile, and leaving group. Ans: Topic: Introduction to Substitution Section 1 Difficulty Level: Easy 11. What is the nucleophile in the following reaction? Ans: A Topic: Introduction to Substitution Section 1 Difficulty Level: Easy 12. What is the electrophile in the following reaction? Ans: B Topic: Introduction to Substitution Section 1 Difficulty Level: Easy 13. What is the leaving group in the following reaction? Sulfur Carbon
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Hydrogen Iodide Ans: D Topic: Alkyl Halides Section 2 Difficulty Level: Easy 14. Which of the following is the correct IUPAC name of the following structure? Chlorocyclopentane 2-Chloro-1-methylcyclopentane 1-Methyl-2-chlorocyclopentane 1-Chloro-2-methylcyclopentane Ans: D Topic: Alkyl Halides Section 2 Difficulty Level: Easy 15. Which of the following is the correct IUPAC name of the following structure? 3-Fluorobutane 2-Fluorobutane (S)-2-Fluorobutane (R)-2-Fluorobutane Ans: C Topic: Alkyl Halides Section 2 Difficulty Level: Medium
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16. Which of the following is the correct IUPAC name of the following structure? 2-Bromo-3-butylpentane (2S)-Bromo-4,5-dimethylheptane 3,4-Dimethyl-6-bromoheptane 2-Bromo-4-methylhexane Ans: B Topic: Alkyl Halides Section 2 Difficulty Level: Easy 17. Which of the following is the correct structure for a compound with the IUPAC name of 2-bromo-3-methylbutane? Ans: A Topic: Alkyl Halides Section 2 Difficulty Level: Easy 18. Which of the following is the correct structure for a compound with the IUPAC name of 1-iodo-3-ethylcyclohexane? Ans: B Topic: Alkyl Halides Section 2 Difficulty Level: Medium 19. Which of the following is the correct structure for a compound with the IUPAC name of (2R)-2-fluorobutane? Ans: D Topic: Alkyl Halides
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Section 2 Difficulty Level: Easy 20. Which of the following compounds has a tertiary carbon? Ans: B Topic: Alkyl Halides Section 2 Difficulty Level: Easy 21. Provide an IUPAC name for the following compound. Ans: 1,1-Dibromocyclopropane Topic: Alkyl Halides Section 2 Difficulty Level: Medium 22. Provide an IUPAC name for the following compound. Ans: 2-Chloro-5-fluorohexane Topic: Alkyl Halides Section 2 Difficulty Level: Medium 23. On the following compound, label all of the primary, secondary, and tertiary carbons. Ans: Topic: Alkyl Halides Section 2 Difficulty Level: Medium 24. Identify the labeled carbon as primary, secondary, or tertiary.
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Ans: tertiary Topic: Alkyl Halides Section 2 Difficulty Level: Easy 25. Identify the labeled carbon as primary, secondary, or tertiary. Ans: primary Topic: Alkyl Halides Section 2 Difficulty Level: Easy 26. Identify the labeled carbon as primary, secondary, or tertiary. Ans: secondary Topic: Possible Mechanisms Section 3 Difficulty Level: Medium 27. Provide a definition of a concerted reaction. Ans: All bond breaking and making occurs at the same time. Topic: Possible Mechanisms Section 3 Difficulty Level: Easy 28. Which of the following is a reasonable definition of a concerted reaction? It is a reaction which takes place in a series of steps. It is a reaction which produces a loud noise. It is a reaction in which all bond-breaking and bond-forming occurs at the same time.
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It is a substitution reaction. Ans: C Topic: Possible Mechanisms Section 3 Difficulty Level: Hard 29. Provide examples of the 4 patterns for steps in the mechanisms of substitution reactions. Ans: 1. Nucleophilic attack, 2. Loss of a leaving group, 3. Proton transfer, and 4. Rearrangement Topic: Possible Mechanisms Section 3 Difficulty Level: Easy 30. Which of the following is not a possible step in a substitution reaction? Ans: D Topic: Possible Mechanisms Section 3 Difficulty Level: Medium 31. Provide an arrow pushing mechanism for the following reaction. Ans: Topic: Possible Mechanisms Section 3 Difficulty Level: Hard 32. Provide an arrow pushing mechanism and product for the following reaction. Ans:
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Topic: Possible Mechanisms Section 3 Difficulty Level: Easy 33. When drawing an arrow-pushing mechanism, the tail of the arrow starts where? At the bond that is being formed. At the bond that is being broken. At the source of electrons that is being moved. At the location to which the electrons are being moved. Ans: C or B Topic: Possible Mechanisms Section 3 Difficulty Level: Easy 34. When drawing an arrow-pushing mechanism, the head of the arrow goes where? At the bond that is being formed. At the bond that is being broken. At the source of electrons that is being moved. At the location to which the electrons are being moved. Ans: D Topic: Possible Mechanisms Section 3 Difficulty Level: Easy 35. Which of the following shows the correct arrow for loss of a bromide leaving group? Ans: A
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Topic: Possible Mechanisms Section 3 Difficulty Level: Hard 36. Provide an arrow-pushing mechanism for the following (intramolecular) reaction. Ans: Topic: SN2 Mechanism Section 4 Difficulty Level: Easy 37. Which of the following is the rate law for the following SN2 reaction? Rate = k[1-bromopropane] Rate = k[NaCN] Rate = k[NaCN][1-bromopropane] Rate = k[NaCN]2 Ans: C Topic: SN2 Mechanism Section 4 Difficulty Level: Medium 38. Write the rate law for the following SN2 reaction. Ans: Topic: SN2 Mechanism Section 4 Difficulty Level: Easy 39. Which of the following is the product of the following SN2 reaction?
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Ans: C Topic: SN2 Mechanism Section 4 Difficulty Level: Hard 40. Which of the following is the product of the following SN2 reaction? Ans: C Topic: SN2 Mechanism Section 4 Difficulty Level: Medium 41. Provide the SN2 product of the following reaction. Ans: Topic: SN2 Mechanism Section 4 Difficulty Level: Medium 42. Provide a mechanism for this reaction. Ans: Topic: SN2 Mechanism Section 4 Difficulty Level: Easy 43. Which of the following is a mechanism for an SN2 reaction? Ans: C Show arrows more carefully in B, C, D Topic: SN2 Mechanism Section 4
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Difficulty Level: Easy 44. Which of the following is the product of the following reaction? Ans: A Topic: SN2 Mechanism Section 4 Difficulty Level: Easy 45. Which of the following is the product of the following reaction? Ans: D Topic: SN2 Mechanism Section 4 Difficulty Level: Easy 46. Which of the following is the product of the following reaction? Ans: A Topic: SN2 Mechanism Section 4 Difficulty Level: Medium 47. What is the product of the following reaction? Ans: Topic: SN2 Mechanism Section 4 Difficulty Level: Medium 48. What is the product of the following reaction? Ans: Topic: SN2 Mechanism
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Section 4 Difficulty Level: Hard 49. From the given starting material, how could you stereospecifically form the given product? Ans: Topic: SN2 Mechanism Section 4 Difficulty Level: Easy 50. Rank the following substrates from most to least reactive in an SN2 reaction. A>B>C>D D>C>B>A A>C>B>D D>C>B>A Ans: C Topic: SN2 Mechanism Section 4 Difficulty Level: Easy 51. Rank the following substrates from most to least reactive in an S N2 reaction. A. A>B>C>D B. D>C>B>A C. C>B>A>D D. D>C>B>A Ans: C Topic: SN2 Mechanism
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Section 4 Difficulty Level: Easy 52. Rank the following substrates from most to least reactive in an S N2 reaction. A. A>B>C>D B. D>C>B>A C. C>B>A>D D. D>C>A>B Ans: B Topic: SN2 Mechanism Section 4 Difficulty Level: Easy 53. Rank the following substrates from most to least reactive in an S N2 reaction. A. A>B>C>D B. C>D>B>A C. C>B>A>D D. D>C>B>A Ans: B Topic: SN2 Mechanism Section 4 Difficulty Level: Hard 54. Draw a reaction diagram for the following reaction. Ans: Topic: SN2 Mechanism Section 4
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Difficulty Level: Medium 55. Which of the following is the reaction diagram for an exothermic, concerted reaction? Ans: C Topic: SN2 Mechanism Section 4 Difficulty Level: Easy 56. Given the following rate law, what will happen to the rate if the concentration of MeI is doubled? Rate = k[Me3N][MeI] It will be doubled. It will not change. It will decrease in half. It will increase very slightly. Ans: A Topic: SN2 Mechanism Section 4 Difficulty Level: Easy 57. Given the following rate law, what will happen to the rate if the concentration of both reactants is doubled? Rate = k[Me3N][MeI] A. It will be doubled. B. It will not change. C. It will decrease in half. D. It will increase 4-fold.
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Ans: D Topic: SN2 Mechanism Section 4 Difficulty Level: Easy 58. Given the following rate law, what will happen to the rate if the concentration of MeI is doubled and the concentration of Me3N is halved? Rate = k[Me3N][MeI] A. It will be doubled. B. It will not change. C. It will decrease in half. D. It will increase very slightly. Ans: B Topic: SN1 Mechanism Section 5 Difficulty Level: Easy 59. Which of the following is the rate law for the following reaction? Rate = k[H2O] Rate = k[H2O][1-chloro-1-methylcyclohexane] Rate = k[1-chloro-1-methylcyclohexane] Rate = k[chloride ion] Ans: C Topic: SN1 Mechanism Section 5 Difficulty Level: Medium
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60. Provide the rate law for the following reaction. Ans: Topic: SN1 Mechanism Section 5 Difficulty Level: Hard 61. Draw a reaction diagram for the following SN1 reaction. Ans: Topic: SN1 Mechanism Section 5 Difficulty Level: Medium 62. Which of the following is a reaction diagram for an SN1 reaction that is endothermic? Ans: B Topic: SN1 Mechanism Section 5 Difficulty Level: Easy 63. Rank the following substrates from most to least reactive in an S N1 reaction. A>B>C>D A>B>D>C D>A>B>C D>C>B>A Ans: A Topic: SN1 Mechanism Section 5
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Difficulty Level: Easy 64. Rank the following substrates from most to least reactive in an S N1 reaction. A. A>B>C>D B. A>B>D>C C. C>A>B>D D. C>D>B>A Ans: D Topic: SN1 Mechanism Section 5 Difficulty Level: Easy 65. Rank the following substrates from most to least reactive in an S N1 reaction. A. A>B>C>D B. A>B>D>C C. D>A>B>C D. D>C>B>A Ans: A Topic: SN1 Mechanism Section 5 Difficulty Level: Easy 66. Rank the following substrates from most to least reactive in an S N1 reaction. A. A>B>C>D B. A>B>D>C C. C>B>A>D D. D>A>B>C
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Ans: C Topic: SN1 Mechanism Section 5 Difficulty Level: Hard 67. Why is a tertiary alkyl halide more reactive in an SN1 reaction than a secondary alkyl halide? Ans: The tertiary cation is more stable. Topic: SN1 Mechanism Section 5 Difficulty Level: Hard 68. Provide a mechanism for the following SN1 reaction. Ans: Topic: SN1 Mechanism Section 5 Difficulty Level: Easy 69. Which of the following is the product of the following reaction? Ans: D Topic: SN1 Mechanism Section 5 Difficulty Level: Easy 70. Which of the following is the product of the following reaction? Ans: B Topic: SN1 Mechanism Section 5
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Difficulty Level: Easy 71. Which of the following is the product of the following reaction? Ans: C Topic: SN1 Mechanism Section 5 Difficulty Level: Easy 72. Which of the following is the product of the following reaction? Ans: A Topic: SN1 Mechanism Section 5 Difficulty Level: Medium 73. Provide the product of the following reaction. Ans: Topic: SN1 Mechanism Section 5 Difficulty Level: Medium 74. What is the product of the following reaction. Include stereochemistry. Ans: Topic: SN1 Mechanism Section 5 Difficulty Level: Easy 75. What is the product of the following reaction. Include stereochemistry. Ans: A Topic: SN1 Mechanism
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Section 5 Difficulty Level: Hard 76. Why does a racemate form at the leaving group carbon in an SN1 reaction? Ans: Because the cationic intermediate is planar and there is equal likelihood of attack of the nucleophile from either face, leading to equal formation of both enantiomers. Topic: Drawing the Complete SN1 Mechanism Section 6 Difficulty Level: Easy 77. Which of the following is a good leaving group? -OH -CH3 -Br -NH2 Ans: C Topic: Drawing the Complete SN1 Mechanism Section 6 Difficulty Level: Medium 78. What is the best leaving group in the following compound? Ans: Topic: Drawing the Complete SN1 Mechanism Section 6 Difficulty Level: Medium 79. Circle the best leaving group in the following compound.
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Ans: Topic: Drawing the Complete SN1 Mechanism Section 6 Difficulty Level: Easy 80. Which of the following must be protonated in order to be a good leaving group? Cl Br NMe2 OH2 Ans: C Topic: Drawing the Complete SN1 Mechanism Section 6 Difficulty Level: Easy 81. Which of the following nucleophiles will require a proton transfer step at the end of the reaction? NMe3 I– OH– H2S Ans: D Topic: Drawing the Complete SN1 Mechanism Section 6 Difficulty Level: Medium
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82. Provide an example of a nucleophile that will require a proton transfer step at the end of the reaction. Ans: Any protic nucleophile (so there are many answers). Topic: Drawing the Complete SN1 Mechanism Section 6 Difficulty Level: Easy 83. Which of the following alkyl halides would likely undergo rearrangement during an SN1 reaction? Ans: B Topic: Drawing the Complete SN1 Mechanism Section 6 Difficulty Level: Easy 84. Which of the following is the major product for the following S N1 reaction? Ans: B Topic: Drawing the Complete SN1 Mechanism Section 6 Difficulty Level: Medium 85. Draw the anticipated major product for the following reaction. Ans: Topic: Drawing the Complete SN1 Mechanism Section 6 Difficulty Level: Hard 86. Draw an energy diagram for the following reaction. Ans:
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Topic: Drawing the Complete SN1 Mechanism Section 6 Difficulty Level: Hard 87. Draw a mechanism for the following reaction. Ans: Topic: Drawing the Complete SN1 Mechanism Section 6 Difficulty Level: Hard 88. What is the anticipated major product for the following reaction? Ans: Topic: Drawing the Complete SN1 Mechanism Section 6 Difficulty Level: Hard 89. What is the mechanism for the following reaction? Ans: Topic: Drawing the Complete SN1 Mechanism Section 6 Difficulty Level: Medium 90. What is the rate law for the following SN1 reaction? Ans: Topic: Drawing the Complete SN2 Mechanism Section 7 Difficulty Level: Easy 91. For the following reaction, which of the following is the mechanism?
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SN1 SN2 Protonation Elimination Ans: B Topic: Drawing the Complete SN2 Mechanism Section 7 Difficulty Level: Easy 92. For the following reaction, which of the following is the product? Ans: D Topic: Drawing the Complete SN2 Mechanism Section 7 Difficulty Level: Easy 93. For the following reaction, which of the following is the rate law? k[HBr] k[1-pentanol] k[HBr][1-pentanol] k[HBr]2 Ans: C Topic: Drawing the Complete SN2 Mechanism Section 7 Difficulty Level: Medium 94. Draw an energy diagram for the following reaction. Ans:
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Topic: Drawing the Complete SN2 Mechanism Section 7 Difficulty Level: Easy 95. For the following reaction, which of the following is the mechanism? A. SN1 B. SN2 C. Protonation D. Elimination Ans: B Topic: Drawing the Complete SN2 Mechanism Section 7 Difficulty Level: Easy 96. For the following reaction, which of the following is the product? Ans: B Topic: Drawing the Complete SN2 Mechanism Section 7 Difficulty Level: Easy 97. For the following reaction, which of the following is the rate law? Rate = k[MeI] Rate = k[t-butanol] Rate = k[MeI][t-butanol] Rate = k[OH] Ans: C Topic: Drawing the Complete SN2 Mechanism
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Section 7 Difficulty Level: Medium 98. Draw an energy diagram for the following reaction. Ans: Topic: Drawing the Complete SN2 Mechanism Section 7 Difficulty Level: Hard 99. For the following reaction, provide the mechanism. Ans: Topic: Drawing the Complete SN2 Mechanism Section 7 Difficulty Level: Medium 100. For the following reaction, draw the product. Ans: Topic: Drawing the Complete SN2 Mechanism Section 7 Difficulty Level: Medium 101. For the following reaction, provide the rate law. Ans: Topic: Drawing the Complete SN2 Mechanism Section 7 Difficulty Level: Medium 102. For the following reaction, provide an energy diagram. Ans:
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Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy 103. What set of reaction conditions should favor an SN2 reaction on 2-bromo-3methylbutane? weak nucleophile in a protic solvent weak nucleophile in an aprotic solvent strong nucleophile in a protic solvent strong nucleophile in an aprotic solvent Ans: D Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy 104. What set of reaction conditions should favor an SN1 reaction on 2-bromo-3methylbutane? A. weak nucleophile in a protic solvent B. weak nucleophile in an aprotic solvent C. strong nucleophile in a protic solvent D. strong nucleophile in an aprotic solvent Ans: A Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy 105. What reaction mechanism is most likely for substitution on the following compound?
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SN1 SN2 Either Neither Ans: C Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy 106. What reaction mechanism is most likely for substitution on the following compound? A. SN1 B. SN2 C. Either D. Neither Ans: B Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy 107. What reaction mechanism is most likely for substitution on the following compound? A. SN1 B. SN2 C. Either D. Neither
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Ans: C Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy 108. What reaction mechanism is most likely for substitution on the following compound? A. SN1 B. SN2 C. Either D. Neither Ans: A Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy 109. What reaction mechanism is most likely for substitution on the following compound? A. SN1 B. SN2 C. Either D. Neither Ans: C Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy
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110. What reaction mechanism is most likely for substitution on the following compound? A. SN1 B. SN2 C. Either D. Neither Ans: D Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy 111. Is the following nucleophile strong or weak? I– Strong Weak Not a nucleophile Ans: A Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy 112. Is the following nucleophile strong or weak? H2O A. Strong B. Weak C. Not a nucleophile
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Ans: B Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy 113. Is the following nucleophile strong or weak? Li+ A. Strong B. Weak C. Not a nucleophile Ans: C Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy 114. Is the following nucleophile strong or weak? HO– A. Strong B. Weak C. Not a nucleophile Ans: A Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy 115. Is the following nucleophile strong or weak? H2S
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A. Strong B. Weak C. Not a nucleophile Ans: A Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy 116. Provide an example of a strong nucleophile. Ans: There are many possible answers. Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy 117. Is the following nucleophile strong or weak? CN– A. Strong B. Weak C. Not a nucleophile Ans: A Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy 118. Is the following nucleophile strong or weak? Na+ A. Strong
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B. Weak C. Not a nucleophile Ans: C Topic: Determining Which Mechanism Section 8 Difficulty Level: Hard 119. Why do polar aprotic solvents favor SN2 reactions? Ans: They raise the energy of the nucleophile, giving a smaller energy of activation for the SN2 pathway. OR They can solvate cations, making the anion more “naked� and thus more nucleophilic. Topic: Determining Which Mechanism Section 8 Difficulty Level: Medium 120. What type of solvent would be best for obtaining an optically active product in the following reaction? polar protic polar aprotic apolar aprotic water Ans: A Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy 121. Which of the following leaving groups would you expect to be the best? Ans: D
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Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy 122. Which of the following solvents is not protic? EtOH H2O NH3 hexane Ans: D Topic: Determining Which Mechanism Section 8 Difficulty Level: Easy 123. What type of solvent is ethanol (EtOH)? polar aprotic apolar aprotic polar protic Ans: C Topic: Selecting Reagents Section 9 Difficulty Level: Easy 124. Which reagents would you use for the following reaction? H2S in water H2S in DMSO NaSH in water
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NaSH in DMSO Ans: D Topic: Selecting Reagents Section 9 Difficulty Level: Easy 125. Which reagents would you use for the following reaction? HN3 in water HN3 in acetonitrile NaN3 in water NaN3 in acetonitrile Ans: D Topic: Selecting Reagents Section 9 Difficulty Level: Easy 126. Which reagents would you use for the following reaction? HCl in water HCl in ether NaCl in water NaCl in DMF Ans: A or B Topic: Selecting Reagents Section 9 Difficulty Level: Medium 127. Which reagents would you use for the following reaction?
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HBr in water NaBr in water Ethyl bromide Ethyl iodide Ans: C Topic: Selecting Reagents Section 9 Difficulty Level: Medium 128. Which reagents would you use for the following reaction? NaOH in water NaOH in acetonitrile Water HCl in water Ans: C Topic: Selecting Reagents Section 9 Difficulty Level: Easy 129. Which reagents would you use for the following reaction? methanol methanol in acetonitrile NaOMe in water NaOMe in acetonitrile Ans: D Topic: Selecting Reagents
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Section 9 Difficulty Level: Hard 130. How would you accomplish the following transformation? Ans: MeOH (SN1 mechanism) Topic: Selecting Reagents Section 9 Difficulty Level: Medium 131. How would you accomplish the following transformation? Ans: NaSH in a polar aprotic solvent Topic: Selecting Reagents Section 9 Difficulty Level: Medium 132. How would you accomplish the following transformation? Ans: H3CCH2Br Topic: Selecting Reagents Section 9 Difficulty Level: Hard 133. How would you accomplish the following transformation? Ans: Topic: Selecting Reagents Section 9 Difficulty Level: Medium 134. How would you accomplish the following transformation? Ans: HBr
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Topic: Selecting Reagents Section 9 Difficulty Level: Medium 135. How would you accomplish the following transformation? Ans: Topic: Selecting Reagents Section 9 Difficulty Level: Easy 136. Which of the following sets of reagents would best accomplish the following transformation? Ans: C Topic: Selecting Reagents Section 9 Difficulty Level: Easy 137. Which of the following sets of reagents would best accomplish the following transformation? Ans: A Topic: Selecting Reagents Section 9 Difficulty Level: Easy 138. Which of the following sets of reagents would best accomplish the following transformation? Ans: D