Chapter 4 Topic: Nomenclature Section 2 Difficulty Level: easy 1. What is the parent chain of the following following compound? compound?
A. octane B. hexane C. heptane D. decane Ans: A Chapter 4 Topic: Nomenclature Section 2 Difficulty Level: medium 2. What is the parent chain of the following following compound? compound?
A. hexane B. heptane C. octane D. nonane Ans: D
Topic: Nomenclature Section 2 Difficulty Level: easy 3. What is the parent chain of the following following compound? compound?
Ans: heptane Topic: Nomenclature Section 2 Difficulty Level: easy 4. What is the name of the parent chain of the following compound?
Ans: heptane Topic: Nomenclature Section 2 Difficulty Level: medium 5. What is the IUPAC IUPAC name of the following compound?
A. 3-isopropyl-5-ethylheptane B. 2-methyl-3-ethyl-5-ethylheptane C. 3,5-diethyl-2-methylheptane D. 2-methyl-3,5-diethylheptane Ans: C Topic: Nomenclature Section 2 Difficulty Level: easy 6. What is the IUPAC IUPAC name of the following compound?
A. 2,5-diethylhexane B. 3,6-dimethyloctane C. 2-ethyl-5-methylheptane D. 2,5-dimethylheptane Ans: B Topic: Nomenclature Section 2 Difficulty Level: easy 7. What is the IUPAC IUPAC name of the following compound?
A. 2,3,5-triethylhexane B. 2,4,5-triethylhexane C. 2,4-diethyl-5-methylheptane D. 4-ethyl-3,6-dimethyloctane Ans: D
Topic: Nomenclature Section 2 Difficulty Level: easy 8. What is the IUPAC IUPAC name of the following compound?
A. 1-ethyl-2-methylcyclohexane B. 2-ethyl-1-methylcyclohexane C. 1-ethyl-2-methylhexane D. cyclononane Ans: A Topic: Nomenclature Section 2 Difficulty Level: easy 9. What is the IUPAC IUPAC name of the following compound?
Ans: 1-ethyl-2-methylcyclohexane Topic: Nomenclature Section 2 Difficulty Level: hard 10. What is the IUPAC name of the following compound?
Ans: 2,7-dimethylbicyclo[3.3.0]octane Topic: Nomenclature Section 2 Difficulty Level: medium 11. What is the IUPAC name of the following compound?
Ans: 3-ethyl-2-methylpentane Topic: Nomenclature Section 2 Difficulty Level: medium 12. What is the IUPAC name of the following compound?
Ans: 5- sec-butyl-4-ethyl-3-methylnonane Topic: Nomenclature Section 2 Difficulty Level: medium 13. What is the IUPAC name of the following compound?
Ans: 1,1,3-trimethyl-cyclopentane Topic: Nomenclature Section 2 Difficulty Level: hard 14. What is the IUPAC name of the following compound?
Ans: 1,1-dimethylbutyl-cyclooctane Topic: Nomenclature Section 2 Difficulty Level: medium 15. What is the structure of an isopropyl group?
Ans: Topic: Nomenclature Section 2 Difficulty Level: easy 16. What is the common name of the following substituent?
A. isopropyl B. tert -butyl -butyl C. isobutyl D. sec-butyl Ans: D
Topic: Nomenclature Section 2 Difficulty Level: easy 17. What is the structure of [2.2.2]bicyclooctane?
Ans: Topic: Nomenclature Section 2 Difficulty Level: easy 18. Which of the following is an isopropyl group?
Ans: A Topic: Nomenclature Section 2 Difficulty Level: easy 19. What is the structure of 3-ethyl-2,4,6-trimethyloctane?
Ans: Topic: Nomenclature Section 2 Difficulty Level: hard 20. What is the structure of 3-ethyl-2-methylpentane?
Ans: Topic: Nomenclature Section 2 Difficulty Level: medium 21. What is the structure of 1-cyclopropyl-3-methylcyclopentane?
Ans:
Topic: Nomenclature Section 2 Difficulty Level: medium 22. What is the IUPAC name of the following compound?
Ans: bicyclo[4.3.2]undecane
Topic: Constitutional Isomers Section 3 Difficulty Level: hard 23. What are the structures and IUPAC names of all constitutional isomers of C6H14?
Ans: Topic: Constitutional Isomers Section 3 Difficulty Level: medium 24. Which pair of the following compounds are constitutional isomers?
Ans: B and C
Topic: Constitutional Isomers Section 3 Difficulty Level: medium
25. Which of the following compounds are constitutional isomers?
Ans: A and D Topic: Constitutional Isomers Section 3 Difficulty Level: easy 26. Which pair of the following compounds are constitutional isomers?
Ans: A and C Topic: Constitutional Isomers Section 3 Difficulty Level: easy 27. What is the relationship between the following two compounds?
A. Constitutional isomers B. The same compound C. Completely different different and not constitutional isomers isomers Ans: A Topic: Constitutional Isomers Section 3 Difficulty Level: easy 28. What is the relationship between the following two compounds?
A. Constitutional isomers B. The same compound C. Completely different different and not constitutional isomers isomers Ans: C
Topic: Constitutional Isomers Section 3 Difficulty Level: easy 29. What is the relationship between the following two compounds?
A. Constitutional isomers B. The same compound C. Completely different different and not constitutional isomers isomers Ans: C Topic: Constitutional Isomers Section 3 Difficulty Level: easy 30. What is the relationship between the following two compounds?
A. Constitutional isomers B. The same compound C. Completely different different and not constitutional isomers isomers Ans: B Topic: Constitutional Isomers Section 3 Difficulty Level: easy 31. What is the relationship between the following two compounds?
A. Constitutional isomers B. The same compound C. Completely different different and not constitutional isomers isomers Ans: A Topic: Relative Stability of Isomeric Isomeric AlkanesSection 4 Difficulty Level: Medium 32. What is the correct stoichiometry of oxygen for the balanced oxidation reaction?
Ans: 8
Topic: Relative Stability of Isomeric Isomeric Alkanes Section 4 Difficulty Level: medium 33. What is the correct stoichiometry of oxygen for the balanced oxidation reaction?
Ans: 9.5 Topic: Relative Stability of Isomeric Isomeric Alkanes Section 4 Difficulty Level: hard 34. Complete the following combustion reaction, assuming that only CO2 and H2O are formed.
Ans: 7.5, 5, 5 Topic: Relative Stability of Isomeric Isomeric Alkanes Section 4 Difficulty Level: hard 35. Complete the following combustion reaction, assuming that only CO2 and H2O are formed.
Ans: 8, 5, 6 Topic: Relative Stability of Isomeric Isomeric Alkanes Section 4 Difficulty Level: medium 36. Of the following isomers of C9H20, which is the most stable? A. nonane B. 3-methyloctane C. 2,2-dimethylheptane D. 2,2,3,4-tetramethylpentane Ans: D Topic: Sources and Uses of Alkanes Section 5 Difficulty Level: medium 37. The reaction shown below is an example of
A. B. C. D.
catalytic cracking thermal cracking catalytic reforming thermal reforming
Ans: B
Topic: Drawing Newman Projections Section 6 Difficulty Level: hard 38. Draw a Newman projection of the following compound as viewed down the indicated bond in the conformation shown.
Ans: Topic: Drawing Newman Projections Section 6 Difficulty Level: hard 39. Draw a Newman projection for the following compound as viewed down the indicated bond in the conformation shown.
Ans: Topic: Drawing Newman Projections Section 6 Difficulty Level: hard 40. Draw a Newman projection for the following compound as viewed down the indicated bond in the conformation shown.
Ans: Topic: Drawing Newman Projections Section 6 Difficulty Level: easy 41. Which of the following is a Newman projection for the following compound as viewed down the indicated bond in the conformation shown?
Ans: A Topic: Drawing Newman Projections Section 6 Difficulty Level: easy 42. Which of the following is a Newman projection for the following compound as viewed down the indicated bond in the conformation shown?
Ans: A Topic: Drawing Newman Projections Section 6 Difficulty Level: easy 43. Which of the following is a Newman projection for the following compound as viewed down the indicated bond in the conformation shown?
Ans: C Topic: Drawing Newman Projections
Section 6 Difficulty Level: easy 44. Which of the following is a wedge and dash structure for the following Newman projection ?
Ans: B Topic: Drawing Newman Projections Section 6 Difficulty Level: easy 45. Which of the following is a wedge and dash structure for the following Newman projection?
Ans: C Topic: Drawing Newman Projections Section 6 Difficulty Level: easy 46. Which of the following is a wedge and dash structure for the following Newman projection?
Ans: B Topic: Drawing Newman Projections Section 6 Difficulty Level: hard 47. Draw a wedge and dash structure of the following Newman projection.
Ans: Topic: Drawing Newman Projections Section 6 Difficulty Level: hard 48. Draw a wedge and dash structure of the following Newman projection.
Ans: Topic: Drawing Newman Projections Section 6 Difficulty Level: hard 49. Draw a wedge and dash structure of the following Newman projection.
Ans: Topic: Drawing Newman Projections Section 6 Difficulty Level: hard 50. Draw a wedge and dash structure that corresponds to the following Newman projection.
Ans: Topic: Conformational Analysis of Ethane/Propane Ethane/Propane Section 7
Difficulty Level: hard 51. Draw the Newman projection for the eclipsed conformation of propane.
Ans: Topic: Conformational Analysis of Ethane/Propane Ethane/Propane Section 7 Difficulty Level: easy 52. Which of the following is/are a Newman projection of an eclipsed conformer?
Ans: C Topic: Conformational Analysis of Ethane/Propane Ethane/Propane Section 7 Difficulty Level: easy 53. Which of the following is/are a Newman projection of a staggered conformer?
Ans: A or D
Topic: Conformational Analysis of Ethane/Propane Ethane/Propane Section 7 Difficulty Level: hard 54. Draw an energy diagram for the conformational analysis of propane.
Ans: Topic: Conformational Analysis of Ethane/Propane Ethane/Propane Section 7 Difficulty Level: hard 55. What is the eclipsing cost of Br and H if the energy difference between the th e staggered and eclipsed conformations of bromoethane is 13 kJ/mol? Ans: 5 kJ/mol Topic: Conformational Analysis of Ethane/Propane Ethane/Propane Section 7 Difficulty Level: hard 56. What is the energy difference between the staggered and eclipsed conformations of 2,2,-dimethylpropane if the eclipsing cost of Me and H is 6 kJ/mol? Ans: 18 kJ/mol Topic: Conformational Analysis of Butane Section 8 Difficulty Level: easy 57. Which of the following following is a gauche conformer?
Ans: A Topic: Conformational Analysis of Butane Section 8 Difficulty Level: easy
58. Which of the following is an anti conformer?
Ans: D Topic: Conformational Analysis of Butane Section 8 Difficulty Level: hard 59. Draw the Newman projection of the conformer of the following compound where the two methyl groups are anti.
Ans: Topic: Conformational Analysis of Butane Section 8 Difficulty Level: hard 60. Draw the gauche conformer of the following compound looking down the indicated bond.
Ans: Topic: Conformational Analysis of Butane Section 8 Difficulty Level: hard 61. Draw the lowest energy conformer of the following compound as a Newman projection looking down the C2-C3 bond.
Ans:
Topic: Conformational Analysis of Butane Section 8 Difficulty Level: hard 62. Draw the lowest energy conformer of the following compound as a Newman projection looking down the C2-C3 bond.
Ans: Topic: Conformational Analysis of Butane Section 8 Difficulty Level: hard 63. Draw an energy diagram for rotation around the indicated bond of the following compound.
Ans:
Topic: Conformational Analysis of Butane Section 8
Difficulty Level: easy 64. Which of the following is the lowest energy conformer of the following compound looking down the indicated bond?
Ans: B Topic: Conformational Analysis of Butane Section 8 Difficulty Level: easy 65. Which of the following is the highest energy conformer of the following compound looking down the indicated bond?
Ans: B or D Topic: Conformational Analysis of Butane Section 8 Difficulty Level: easy 66. Which of the following is the highest energy conformer of the following compound?
Ans: C Topic: Conformational Analysis of Butane Section 8 Difficulty Level: easy 67. Which of the following is the highest energy conformer of the following compound?
Ans: C Topic: Cycloalkanes Section 9 Difficulty Level: easy 68. Which of the following cycloalkanes has the most angle strain? strain?
Ans: B Topic: Cycloalkanes Section 9 Difficulty Level: easy 69. Which of the following cycloalkanes has th e least angle strain?
Ans: C Topic: Conformations of Cyclohexane Section 10 Difficulty Level: easy 70. Which of the following is a boat conformation conformation of cyclohexane?
Ans: A Topic: Conformations of Cyclohexane Section 10 Difficulty Level: medium 71. Draw the chair conformation of cyclohexane.
Ans: Topic: Conformations of Cyclohexane Section 10 Difficulty Level: easy 72. Which of the following is a chair conformation of cyclohexane?
Ans: B Topic: Drawing Chair Conformations Section 11 Difficulty Level: medium 73. Draw a chair conformation of methylcyclohexane.
Ans: Topic: Drawing Chair Conformations Section 11 Difficulty Level: easy 74. Which of the following is a chair conformation of the following substituted cyclohexane?
Ans: A Topic: Drawing Chair Conformations Section 11 Difficulty Level: easy 75. Is the following labeled H axial or equatorial? eq uatorial?
Ans: Equatorial Topic: Drawing Chair Conformations Section 11
Difficulty Level: hard 76. Draw a chair conformation of ethylcyclohexane with the ethyl group axial.
Ans: Topic: Drawing Chair Conformations Section 11 Difficulty Level: hard 77. Draw a chair conf ormation ormation of cyclohexane showing all of the equatorial H’s.
Ans: Topic: Drawing Chair Conformations Section 11 Difficulty Level: easy 78. Which of the following illustrates an axial OH?
Ans: B Topic: Drawing Chair Conformations Section 11 Difficulty Level: easy 79. Which of the following illustrates an equatorial OH?
Ans: A
Topic: Drawing Chair Conformations Section 11 Difficulty Level: medium 80. Draw in all of the axial hydrogens on the cyclohexane chair conformation shown.
Ans:
Topic: Monosubstituted Cyclohexanes Section 12 Difficulty Level: hard 81. Draw both chair conformers of the following following compound. compound.
Ans: Topic: Monosubstituted Cyclohexanes Section 12 Difficulty Level: hard 82. Draw both chair conformers of the following compound.
Ans: Topic: Monosubstituted Cyclohexanes Section 12 Difficulty Level: easy 83. Which is the most stable chair conformer of the following compound?
Ans: A Topic: Monosubstituted Cyclohexanes Section 12 Difficulty Level: easy
84. Which is the most stable chair conformer of the following compound?
Ans: A Topic: Monosubstituted Cyclohexanes Section 12 Difficulty Level: easy 85. Which is the least stable chair conformer of the following compound?
Ans: D Topic: Monosubstituted Cyclohexanes Section 12 Difficulty Level: easy 86. Which is the least stable chair conformer of the following compound?
Ans: D Topic: Monosubstituted Cyclohexanes Section 12 Difficulty Level: easy 87. Which is the other chair conformer of the following compound?
Ans: D
Topic: Monosubstituted Cyclohexanes Section 12 Difficulty Level: medium 88. Draw the other chair conformer of the following compound.
Ans: Topic: Monosubstituted Cyclohexanes Section 12 Difficulty Level: easy 89. Draw the most stable chair conformer of the following compound.
Ans: Topic: Monosubstituted Cyclohexanes Section 12 Difficulty Level: easy 90. Draw the most stable chair conformer of the following compound.
Ans: 91. Topic: Disubstituted Cyclohexanes Section 13 Difficulty Level: hard 92. Draw the most stable chair conformer of the most stable isomer of 1,3,5trimethylcyclohexane.
Ans: Topic: Disubstituted Cyclohexanes Section 13 Difficulty Level: hard
93. Draw the most stable chair conformer of the most stable isomer of 1-ethyl-3isopropylcyclohexane.
Ans: Topic: Disubstituted Cyclohexanes Section 13 Difficulty Level: easy 94. Which of the following is the most stable conformer of the most stable isomer of 1,4-diethylcyclohexane?
Ans: C Topic: Disubstituted Cyclohexanes Section 13 Difficulty Level: easy 95. Which of the following is the least stable chair conformer of the most stable isomer of 1,4-diethylcyclohexane?
Ans: A Topic: Disubstituted Cyclohexanes Section 13 Difficulty Level: easy 96. Which of the following is the most stable conformer of the most stable isomer of 1,2,4-trimethylcyclohexane?
Ans: C Topic: Disubstituted Cyclohexanes Section 13
Difficulty Level: easy 97. Which of the following is the least stable chair conformer of the most stable isomer of 1,2,4-trimethylcyclohexane?
Ans: A Topic: Disubstituted Cyclohexanes Section 13 Difficulty Level: hard 98. Which of the following is the most stable chair conformation of the following cyclohexane?
Ans: D
Topic: Disubstituted Cyclohexanes Section 13 Difficulty Level: hard 99. Draw the most stable chair conformation of the following cyclohexane.
Ans: Topic: Disubstituted Cyclohexanes Section 13 Difficulty Level: hard 100. Draw the most stable chair conformation of the following cyclohexane.
Ans:
Topic: Disubstituted Cyclohexanes Section 13 Difficulty Level: easy 101. Which of the following is the most stable conformer of the most stable isomer of 1-ethyl-2,4-dimethylcyclohexane?
Ans: C Topic: Disubstituted Cyclohexanes Section 13 Difficulty Level: easy 102. Which of the following is the least stable chair conformer of the most stable isomer of 1-ethyl-2,4-dimethylcyclohexane?
Ans: A Topic: Disubstituted Cyclohexanes Section 13 Difficulty Level: hard 103. Rank the following conformers of the isomers of 1-ethyl-2,4dimethylcyclohexane from most to least stable.
Ans: C>D>B>A Topic: Cis-Trans Section 14 Difficulty Level: easy 104. Are the two substituents cis or trans?
A. trans B. cis C. neither Ans: A Topic: Cis-Trans Section 14 Difficulty Level: easy 105. Are the two substituents cis or trans?
A. trans B. cis C. neither Ans: B Topic: Cis-Trans Section 14 Difficulty Level: easy 106. Are the two substituents cis or trans?
A. trans B. cis C. neither Ans: A Topic: Cis-Trans Section 14 Difficulty Level: easy 107. Are the two substituents cis or trans?
A. trans B. cis C. neither Ans: A Topic: Cis-Trans Section 14 Difficulty Level: hard 108. Draw the most stable conformation of trans-1,4-diethylcyclohexane.
Ans: Topic: Cis-Trans Section 14 Difficulty Level: hard 109. Draw the most stable chair conformer of cis-1,4-diethylcyclohexane.
Ans: Topic: Cis-Trans Section 14 Difficulty Level: medium 110. Which is more stable?
A. A B. B C. neither Ans: B
Topic: Cis-Trans Section 14 Difficulty Level: medium 111. Which is more stable?
A. A B. B C. neither Ans: B Topic: Cis-Trans Section 14
Difficulty Level: medium 112. Which of the following is the most stable isomer?
Ans: D Topic: Cis-Trans Section 14 Difficulty Level: hard 113. Draw the lowest energy chair conformer of the most stable isomer of 4isopropyl-1,2-dimethylcyclohexane.
Ans:
Topic: Nomenclature + Spectroscopy Section 2, and Chapter 15 Difficulty Level: medium 114. How many distinct signals would appear in the (proton-decoupled) 13C NMR spectrum of 2,4-dimethylpentane? A. 2 B. 3 C. 4 D. 5 Ans: B
Topic: Nomenclature + Spectroscopy Section 2, and Chapter 15 Difficulty Level: medium 115. How many distinct resonances would appear in the (proton-decoupled) 13C NMR spectrum of 1,1-diethyl-3-methylcyclobutane? A. 4 B. 5 C. 6 D. 7 Ans: C
