Organic Chemistry, 8e (Brown) Chapter 2

1. Approximately how long is a C?C single bond of an alkane?   a.  111 pm   b.  134 pm   c.  142 pm   d.  153 pm ANSWER:   d POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 2. What is the approximate C?C?C bond angle in propane?   a.  90°   b.  109°   c.  120°   d.  180° ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 3. What is the name of the linear hydrocarbon with the molecular formula C7H16?   a.  hexane   b.  heptane   c.  decane   d.  undecane ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 4. What is the name of the linear hydrocarbon with the molecular formula C11H24?   a.  heptane   b.  decane   c.  undecane   d.  eicosane ANSWER:   c POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 5. How many hydrogen atoms are there in nonane, the linear hydrocarbon with nine carbon atoms?   a.  16   b.  18   c.  20   d.  22 ANSWER:   c POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 6. How many hydrogen atoms are there in dodecane, the linear hydrocarbon with twelve carbon atoms?   a.  12   b.  20   c.  24   d.  26 ANSWER:   d POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 7. How many constitutional isomers are there with the molecular formula C4H10?   a.  2   b.  3   c.  4   d.  5 ANSWER:   a POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 8. How many constitutional isomers are there with the molecular formula C5H12?   a.  2   b.  3   c.  4   d.  5 ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 9. How many constitutional isomers are there with the molecular formula C6H14?   a.  3   b.  4   c.  5   d.  8 ANSWER:   c POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 10. What is the IUPAC name of the following compound?   a.  3-propylpentane   b.  1,1-diethylpropane   c.  3-ethylhexane   d.  isooctane ANSWER:   c POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 11. What is the IUPAC name of the following compound?   a.  2-ethyl-4-methylpentane   b.  2,4-dimethylhexane   c.  3,5-dimethylhexane   d.  1,1,3-trimethylpentane ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 12. What is the IUPAC name of the following compound?   a.  2,2-dimethyl-4-ethylheptane   b.  4-ethyl-2,2-dimethyl-heptane   c.  6,6-dimethyl-4-ethylheptane   d.  4-ethyl-6,6-dimethyl-heptane ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 13. What is the IUPAC name of the following compound?   a.  5,5-dimethyl-3-ethylheptane   b.  5-ethyl-3,3-dimethyl-heptane   c.  3,3-dimethyl-5-ethylheptane   d.  3-ethyl-5,5-dimethyl-heptane ANSWER:   d POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 14. What is the IUPAC name of the following compound?   a.  2-isopropyl-5-methylpentane   b.  5-isopropyl-2-methylpentane   c.  2,3,5-trimethylhexane   d.  1,2-diisopropylpropane ANSWER:   c POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 15. What is the IUPAC name of the following compound?   a.  2,4-dimethyl-3-isopropyl-pentane   b.  3-isopropyl-1,5-dimethylpentane   c.  3-isopropyl-2,4-dimethylpentane   d.  triisopropylmethane ANSWER:   c POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 16. Which of the following compounds has 1°, 2°, 3° and 4° carbon atoms?   a.  hexane   b.  2-methylhexane   c.  2,2-dimethylhexane   d.  2,2,3-trimethylhexane ANSWER:   d POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 17. Which of the following compounds has only 1° and 3° carbon atoms?   a.  hexane   b.  2-methylpentane   c.  3-methylpentane   d.  2,3-dimethylbutane ANSWER:   d POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 18. What is the correct assignment of common names for the following molecules?   a.  i = butane; ii = neopentane; iii = isopentane   b.  i = neobutane; ii = isobutane; iii = pentane   c.  i = butane; ii = isobutane; iii = isopentane   d.  i = butane; ii = isobutane; iii = neopentane ANSWER:   d POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 19. What is the correct assignment of common names for the following molecules?   a.  i = pentane; ii = isopentane; iii = neopentane   b.  i = neopentane; ii = isopentane; iii = pentane   c.  i = pentane; ii = neopentane; iii = isopentane   d.  i = neopentane; ii = pentane; iii = isopentane ANSWER:   a POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 20. What is the IUPAC name of the following compound?   a.  1-isopropyl-4,6-dimethylcyclohexane   b.  1-isopropyl-2,4-dimethylcyclohexane   c.  4-isopropyl-1,3-dimethylcyclohexane   d.  4-isopropyl-1,5-dimethylcyclohexane ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 21. What is the IUPAC name of the following compound?   a.  1-methylbicyclo[2.2.1]heptane   b.  2-methylbicyclo[2.2.1]heptane   c.  3-methylbicyclo[2.2.1]heptane   d.  4-methylbicyclo[2.2.1]heptane ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 22. What is the IUPAC name of the following compound?   a.  bicyclo[4.3]nonane   b.  bicyclo[4.3.0]nonane   c.  bicyclo[6.5]nonane   d.  bicyclo[6.5.0]nonane ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 23. What is the IUPAC name for the following compound?   a.  cycloheptane   b.  bicyclo[3.2.0]heptane   c.  bicyclo[5.4]heptane   d.  cyclobutylcyclopentane ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 24. What is the IUPAC name for the following compound?   a.  bicyclo[5.4.3]octane   b.  bicyclo[3.2.1]octane   c.  bicyclo[3.2.1]hexane   d.  bicyclo[2.2.1]octane ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 25. Which of the following Newman projections does not represent 2-methylhexane?   a.  1   b.  2   c.  3   d.  4 ANSWER:   c POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 26. Which of the following Newman projections represents 2,4-dimethylpentane?   a.  1   b.  2   c.  3   d.  4 ANSWER:   a POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 27. Which of the following Newman projections represents the most stable conformation of 2,3-dimethylbutane?   a.  1   b.  2   c.  3   d.  4 ANSWER:   c POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 28. Which of the following Newman projections represents the most stable conformation of 2-methylbutane?   a.  1   b.  2   c.  3   d.  4 ANSWER:   a POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 29. Which of the following cycloalkanes has the most ring strain?   a.  cyclopropane   b.  cyclobutane   c.  cyclopentane   d.  cyclohexane ANSWER:   a POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 30. Which of the following cycloalkanes has the least ring strain?   a.  cyclopropane   b.  cyclopentane   c.  cyclohexane   d.  cycloheptane ANSWER:   c POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 31. Which of the following structures represents trans-1,3-dimethylcyclohexane?   a.  1   b.  2   c.  3   d.  4 ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 32. Which of the following structures represents trans-1,2-dimethylcyclohexane?   a.  1   b.  2   c.  3   d.  4 ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 33. Which of the following is the most stable conformation of cis-1-isopropyl-3-methylcyclohexane?   a.  1   b.  2   c.  3   d.  4 ANSWER:   c POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 34. Which of the following is the most stable conformation of trans-1-ethyl-3-methylcyclohexane?   a.  1   b.  2   c.  3   d.  4 ANSWER:   d POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 35. Which of the following alkanes has the highest boiling point?   a.  propane   b.  butane   c.  pentane   d.  hexane ANSWER:   d POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 36. Which of the following alkanes has the highest boiling point?   a.  2,3-dimethylbutane   b.  2-methylpentane   c.  3-methylpentane   d.  hexane ANSWER:   d POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 37. What is the IUPAC name of the following compound?   a.  trans-1-isopropyl-4-methylcyclohexane   b.  cis-1-isopropyl-4-methylcyclohexane   c.  cis-2-isopropyl-5-methylcyclohexane   d.  cis-1-tert-butyl-4-methylcyclohexane ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 38. What is the IUPAC name of the following compound?   a.  trans-1-isopropyl-4-methylcyclopentane   b.  cis-1-tert-butyl-2-methylcyclopentane   c.  trans-1-tert-butyl-2-methylcyclopentane   d.  cis-1-isopropyl-2-methylcyclopentane ANSWER:   c POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 39. Which one of the following structures represents a different compound from the other three?   a.  1   b.  2   c.  3   d.  4 ANSWER:   d POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 40. Which one of the following structures represents a different compound from the other three?   a.  1   b.  2   c.  3   d.  4 ANSWER:   c POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 41. In which of the following compounds are all of the carbon atoms in the same plane?   a.  cyclopropane   b.  cyclobutane   c.  cyclopentane   d.  cyclohexane ANSWER:   a POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 42. Which of the following compounds can adopt a chair conformation in which there are no axial methyl groups?   a.  1,1-dimethylcyclohexane   b.  cis-1,2-dimethylcyclohexane   c.  trans-1,2-dimethylcyclohexane   d.  cis-1,3-dimethylcyclohexane ANSWER:   c POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 43. Which of the following compounds can adopt a chair conformation in which there are no axial methyl groups?   a.  cis-1,2-dimethylcyclohexane   b.  cis-1,3-dimethylcyclohexane   c.  trans-1,3-dimethylcyclohexane   d.  cis-1,4-dimethylcyclohexane ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 44. Which of the following statements is not true regarding the conformation of substituted cyclohexanes?   a.  ring inversion of cyclohexane between two chair conformations takes place via a boat conformation   b.  substituted cyclohexanes are destabilized by 1,3-diaxial interactions   c.  the boat conformation of cyclohexane is usually more stable than the chair conformation   d.  the relative amount of two conformations of substituted cyclohexanes can be determined from the difference in strain energy ANSWER:   c POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 45. What is the approximate dihedral angle between the two chlorine atoms in cis-1,2-dichlorocyclohexane?   a.  0°   b.  60°   c.  120°   d.  180° ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 46. What is the approximate dihedral angle between the two chlorine atoms in the diequatorial conformation of trans-1,2-dichlorocyclohexane?   a.  0°   b.  60°   c.  120°   d.  180° ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 47. What is the approximate dihedral angle between the two chlorine atoms in the diaxial conformation of trans-1,2-dichlorocyclohexane?   a.  0°   b.  60°   c.  120°   d.  180° ANSWER:   d POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 48. Which of the following is not true regarding the properties of alkanes?   a.  alkanes are nonpolar   b.  alkanes burn in air to give H2O and CO2   c.  alkanes are highly miscible with water   d.  the strongest intermolecular force between alkane molecules is the van der Waals interaction ANSWER:   c POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 49. Which of the following undergoes the most exothermic combustion?   a.  octane   b.  2-methylheptane   c.  2,2-dimethylhexane   d.  2,2,3,3-tetramethylbutane ANSWER:   a POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 50. How many moles of molecular oxygen (O2) are consumed in the complete combustion of one mole of octane (C8H18)?   a.  12.5   b.  13   c.  17   d.  26 ANSWER:   a POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 51. How many moles of molecular oxygen (O2) are consumed in the complete combustion of one mole of hexane (C6H14)?   a.  6   b.  9.5   c.  12.5   d.  14 ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 52. Which of the following statements is not true?   a.  Combustion of an alkane is an exothermic reaction.   b.  The heat of combustion of propane is three times that of methane.   c.  The constitutional isomers of C7H16 have different heats of combustion from one another   d.  The products of combustion of an alkane are H2O and CO2. ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 53. Which of the following is the steroid nucleus?   a.  1   b.  2   c.  3   d.  4 ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 54. Which of the following cycloalkanes has the largest heat of combustion?   a.  cyclopropane   b.  cyclobutane   c.  cyclopentane   d.  cyclohexane ANSWER:   d POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 55. Which of the following cycloalkanes has the largest heat of combustion per carbon atom?   a.  cyclopropane   b.  cyclopentane   c.  cyclohexane   d.  cycloheptane ANSWER:   a POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 56. Which of the following cycloalkanes has the smallest heat of combustion per carbon atom?   a.  cyclopropane   b.  cyclopentane   c.  cyclohexane   d.  cycloheptane ANSWER:   c POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 57. Which of the following structures is different from the other three?   a.  1   b.  2   c.  3   d.  4 ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 58. Which of the following structures is different from the other three?   a.  1   b.  2   c.  3   d.  4 ANSWER:   a POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 59. Which of the following substituted cyclohexanes has the most negative value of ?G° for ring flipping from the conformation in which the substituent is axial to the one where it is equatorial?   a.  methylcyclohexane   b.  chlorocyclohexane   c.  isopropylcyclohexane   d.  ethynylcyclohexane ANSWER:   c POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 60. Which of the following substituted cyclohexanes has the most negative value of ?G° for ring flipping from the conformation in which the substituent is axial to the one where it is equatorial?   a.  fluorocyclohexane   b.  methylcyclohexane   c.  ethylcyclohexane   d.  tert-butylcyclohexane ANSWER:   d POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 61. The Newman projection of the gauche conformation of 1,2-dichloroethane is shown below.                                             a.  True   b.  False ANSWER:   True POINTS:   1 QUESTION TYPE:   True / False HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/10/2017 1:33 AM 62. The most stable conformation of an alkane occurs when carbon?carbon bonds are staggered and bulky groups are anti.   a.  True   b.  False ANSWER:   True POINTS:   1 QUESTION TYPE:   True / False HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 63. The following pairs of Newman projections represent the same compound but in differing conformations.                               a.  True   b.  False ANSWER:   False POINTS:   1 QUESTION TYPE:   True / False HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/10/2017 1:38 AM 64. There are four constitutional isomers for the molecular formula C6H14.   a.  True   b.  False ANSWER:   False POINTS:   1 QUESTION TYPE:   True / False HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 65. The following Newman projection represents 2-methylhexane.                           a.  True   b.  False ANSWER:   False POINTS:   1 QUESTION TYPE:   True / False HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/10/2017 1:37 AM 66. The following structures represent, from left to right,  a cis and a trans isomer.                   a.  True   b.  False ANSWER:   True POINTS:   1 QUESTION TYPE:   True / False HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/10/2017 1:37 AM 67. The following structures represent a pair of constitutional isomers.                   a.  True   b.  False ANSWER:   False POINTS:   1 QUESTION TYPE:   True / False HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/10/2017 1:38 AM 68. 3-methylhexylcyclopentane represents a correct IUPAC name.   a.  True   b.  False ANSWER:   False POINTS:   1 QUESTION TYPE:   True / False HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 69. In the following structure the positions labeled a and d are equatorial positions.                                 a.  True   b.  False ANSWER:   True POINTS:   1 QUESTION TYPE:   True / False HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/13/2017 2:28 AM 70. In the following conversion,  the conformations are of equal stability.         a.  True   b.  False ANSWER:   True POINTS:   1 QUESTION TYPE:   True / False HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/10/2017 4:39 AM 71. The correct IUPAC name for the following compound is___________________________.                                       ANSWER:   3-methyl-5-(1-methylethyl)octane 3-methyl-5-isopropyloctane POINTS:   1 QUESTION TYPE:   Completion HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/13/2017 2:29 AM 72. The tertiary carbon atom in the following structure is indicated by the letter_____.                                             ANSWER:   b B POINTS:   1 QUESTION TYPE:   Completion HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/13/2017 2:30 AM Match the Newman projection for the conformation of 2-methylbutane to the indicated position on the potential energy diagram.                                       ? A B C D 73. Conformation A is represented by Roman numeral ____. ANSWER:   II POINTS:   1 QUESTION TYPE:   Completion HAS VARIABLES:   False PREFACE NAME:   PE Diagram DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 74. Conformation B is represented by Roman numeral ____. ANSWER:   III POINTS:   1 QUESTION TYPE:   Completion HAS VARIABLES:   False PREFACE NAME:   PE Diagram DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 75. Conformation C is represented by Roman numeral ____. ANSWER:   IV POINTS:   1 QUESTION TYPE:   Completion HAS VARIABLES:   False PREFACE NAME:   PE Diagram DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 76. Conformation D is represented by Roman numeral ____. ANSWER:   I POINTS:   1 QUESTION TYPE:   Completion HAS VARIABLES:   False PREFACE NAME:   PE Diagram DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 77. What is the IUPAC name of the following compound? ANSWER:   4-ethyl-2-methylhexane POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 78. What is the IUPAC name of the following compound? ANSWER:   3-ethyl-2-methylhexane POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 79. What is the IUPAC name of the following compound? ANSWER:   2,4,4-trimethylhexane POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 80. What is the IUPAC name of the following compound? ANSWER:   2,2,4-trimethylhexane POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 81. What is the IUPAC name of the following compound? ANSWER:   bicyclo[4.2.0]octane POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 82. What is the IUPAC name of the following compound? ANSWER:   bicyclo[2.2.1]heptane POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 83. What is the IUPAC name of the following compound? ANSWER:   cis-1-tert-butyl-2-methylcyclohexane [ignoring absolute stereochemistry in Chap 2] POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 84. What is the IUPAC name of the following compound? ANSWER:   cis-1-isopropyl-3-methylcyclohexane [ignoring absolute stereochemistry in Chap 2] POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 85. How many hydrogen atoms are there in decane? ANSWER:   22 POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 86. How many hydrogen atoms are there in octane? ANSWER:   18 POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 87. What are the common and IUPAC names of the following compound? ANSWER:   common: neopentane IUPAC: 2,2-dimethylpropane POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 88. What are the common and IUPAC names of the following compound? ANSWER:   common: isopentane IUPAC: 2-dimethylbutane POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 89. What is the IUPAC name of the following compound? ANSWER:   butanal POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 90. What is the IUPAC name of the following compound? ANSWER:   butanone POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 91. Provide a line-bond structure of hexanoic acid. ANSWER:   POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 92. Provide a line-bond structure of pentanal. ANSWER:   POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 93. Provide a Newman projection of the most stable conformation of 2-methylpentane, (CH3)2CHCH2CH2CH3, looking along the C2-C3 bond ANSWER:   POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/10/2017 5:50 AM 94. Provide a Newman projection of the most stable conformation of 3-methylpentane, CH3CH2CH(CH3)CH2CH3 looking along the C2-C3 bond. ANSWER:   POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 95. Provide a neatly drawn plot of energy versus dihedral angle for rotation around the C2-C3 bond of butane. ANSWER:   POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 96. Provide a neatly drawn plot of energy versus dihedral angle for rotation around the C-C bond of ethane. ANSWER:   POINTS:   1 QUESTION TYPE:   Subjective Short Answer HAS VARIABLES:   False DATE CREATED:   3/12/2015 3:24 PM DATE MODIFIED:   3/12/2015 3:24 PM 97. Identify the constitutional isomer with the molecular formula C7H16. ?   a.  Only I   b.  Only I and II   c.  Only II   d.  I, II, and III ANSWER:   c POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   4/11/2017 7:38 AM DATE MODIFIED:   4/13/2017 1:02 AM 98. The molecular formulas of neopentane and isobutane are _____ and _____, respectively.   a.  C5H12; C4H8   b.  C5H10; C4H10   c.  C5H12; C4H11   d.  C5H12; C4H10 ANSWER:   d POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   4/11/2017 7:54 AM DATE MODIFIED:   4/11/2017 7:55 AM 99. The total numbers of 2? and 3? carbon atoms in the following structure are _____ and _____, respectively. ?   a.  3; 7   b.  7; 4   c.  4; 6   d.  6; 4 ANSWER:   b POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   4/11/2017 7:57 AM DATE MODIFIED:   4/11/2017 8:00 AM 100. What is “X” in the following reaction? ?   a.    b.    c.    d.  ANSWER:   a POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   4/11/2017 8:01 AM DATE MODIFIED:   4/11/2017 8:09 AM 101. What is “X” in the following reaction? ?   a.    b.    c.    d.  ANSWER:   a POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   4/11/2017 8:04 AM DATE MODIFIED:   4/11/2017 8:09 AM 102. What is “X” in the following reaction? ?   a.    b.    c.    d.  ANSWER:   d POINTS:   1 QUESTION TYPE:   Multiple Choice HAS VARIABLES:   False DATE CREATED:   4/11/2017 8:10 AM DATE MODIFIED:   4/19/2017 12:56 AM Match the structures with their IUPAC names. a.  b.  c.  QUESTION TYPE:   Matching HAS VARIABLES:   False DATE CREATED:   4/11/2017 8:15 AM DATE MODIFIED:   4/11/2017 8:26 AM 103. 3-ethyl-2-methylhexane ANSWER:   a POINTS:   1 104. 4-ethyl-2,2-dimethylhexane ANSWER:   b POINTS:   1 105. 4-ethyl-2-methylhexane ANSWER:   c POINTS:   1