Chapter 4                                                    Chapter 4MULTIPLE CHOICE QUESTIONS Solomons Chapter 4        ...
Chapter 4                                                               Chapter 4Topic: Nomenclature                      ...
Chapter 4                                                                  Chapter 4                                      ...
Chapter 4                                                                                 Chapter 435. An IUPAC name for t...
Chapter 4                                                                           Chapter 4Topic: Ring Strain 41-47     ...
Chapter 4                                                                                           Chapter 450. The most ...
Chapter 4                                                                                                   Chapter 4Topic...
Chapter 4                                                                    Chapter 4                                    ...
Chapter 4                                                                                           Chapter 4   67. Which ...
Chapter 4                                                                                       Chapter 4Topic: Alkane Syn...
Chapter 4                                                         Chapter 4Svar Test banken Solomons Chapt. 4             ...
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  1. 1. Chapter 4 Chapter 4MULTIPLE CHOICE QUESTIONS Solomons Chapter 4 Topic: Nomenclature(Answers on pages 21-22) Uppgifter markerade * är överkurs 5. Which of the following pairs of compounds represent pairs of constitutional isomers?Topic: Nomenclature A) 2-Methylbutane and pentane 1. B) 2-Chlorohexane and 3-chlorohexane C) sec-Butyl bromide and tert-butyl bromide D) Propyl chloride and isopropyl chloride The IUPAC name for is: E) All of the above A) 6-Ethyl-3,4-dimethylheptane B) 2-Ethyl-4,5-dimethylheptane 6. Which of the following is bicyclo[3.2.2]nonane*? C) 3,4,6-Trimethyloctane D) 3,5,6-Trimethyloctane E) 2-(1-Methylpropyl)-4-methylhexane 2. I II III An IUPAC name for is: A) 5-Methyl-4-(1-methylpropyl)hexane IV V B) 2-Methyl-3-(1-methylpropyl)hexane A) I C) 2-Methyl-3-(2-methylpropyl)hexane B) II D) 3-Methyl-4-(1-methylethyl)heptane C) III E) 5-Methyl-4-(1-methylethyl)heptane D) IV E) V 3. A correct IUPAC name for the following compound is: 7. Select the systematic name for Cl H H Cl A) 2,5-Dimethyl-3-propylheptane A) cis-1,3-Dichlorocyclopentane B) 3,6-Dimethyl-5-propylheptane B) trans-1,4-Dichlorocyclopentane C) 6-Methyl-4-(1-methylethyl)octane C) cis-1,2-Dichlorocyclopentane D) 2-Methyl-3-(2-methylbutyl)hexane D) trans-1,3-Dichlorocyclopentane E) 3-Methyl-5-(1-methylethyl)octane E) 1,1-Dichlorocyclopentane 4. A correct IUPAC name for the following compound is: 9. Which isomer of C5H10 would you expect to have the smallest heat of combustion*? A) Cyclopentane B) Methylcyclobutane C) 1,1-Dimethylcyclopropane OH Cl D) cis-1,2-Dimethylcyclopropane A) 4-propyl-5-chloro-3-heptanol E) trans-1,2-Dimethylcyclopropane B) 4-propyl-3-chloro-5-heptanol C) 4-(1-chloropropyl)-3-heptanol D) 5-chloro-4-propyl-3-heptanol E) 3-hydroxy-4-propyl-5-chloroheptane 87 88
  2. 2. Chapter 4 Chapter 4Topic: Nomenclature 20. cis-1,3-Dibromocyclohexane is represented by structure(s): Br Br H H 12. What is the common name for this compound? Br H H Br Br Br Br H H A) Isobutyl bromide I II III B) tert-Butyl bromide A) I C) Butyl bromide B) II D) sec-Butyl bromide C) III E) Bromo-sec-butane D) II and III E) I and II 13. A correct IUPAC name for the following compound is: 21. CH3CHCH2! Br An IUPAC name for the group CH2CH3 is: A) Isopentyl B) Isoamyl A) 3,6,7-trimethyl-4-bromo-1-octene C) sec-Butylmethyl B) 4-bromo-3-methyl-6-isopropyl-1-heptene D) 2-Methylbutyl C) 4-bromo-3,6,7-trimethyl-1-octene E) 2-Ethylpropyl D) 4-bromo-6-isopropyl-3-methyl-1-heptene 22. The neopentyl group has the alternative name: A) 1,1-DimethylpropylUse the following to answer questions 18-19: B) 1,2-Dimethylpropyl Br H H C) 2,2-DimethylpropylBr Br Br D) 1-Methylbutyl E) 2-Methylbutyl H Br Br H H H I II III 23. Br 18. trans-1,2-Dibromocyclohexane is represented by structure(s): A) I The correct IUPAC name for Cl is: B) II A) 2-Bromo-4-chloro-4-isopropylpentane C) III B) 4-Bromo-2-chloro-2-isopropylpentane D) II and III C) 5-Bromo-3-chloro-2,3-dimethylhexane E) I and II D) 2-Bromo-4-chloro-4,5-dimethylhexane E) 2-(2-Bromopropyl)-2-chloro-3-methylbutane 19. cis-1,2-Dibromocyclohexane is represented by structure(s): A) I 24. Which of the following is a correct name which corresponds to the common name tert- B) II pentyl alcohol*? C) III A) 2,2-Dimethyl-1-propanol D) II and III B) 2-Ethyl-2-propanol E) I and II C) 2-Methyl-2-butanol D) 3-Methyl-1-butanol E) Methyl tert-butanol Topic: Nomenclature 89 90
  3. 3. Chapter 4 Chapter 4 31. Neglecting stereochemistry, which of these common group names is ambiguous, i.e.,25. The correct IUPAC name for the following compound is: does not refer to one specific group*? OH A) Butyl B) sec-Butyl C) tert-Pentyl D) Neopentyl E) sec-Pentyl 32. What is the correct IUPAC name for the following compound?A) 1-Hydroxy-3-sec-butylcyclopentane OHB) 3-sec-Butyl-1-cyclopentanolC) 1-sec-Butyl-3-cyclopentanolD) 4-sec-Butyl-1-cyclopentanol A) 5-Ethyl-3-methylhexanolE) 3-Isobutyl-1-cyclopentanol B) 5-Ethyl-3-methyl-1-hexanol C) 2-Ethyl-4-methyl-6-hexanol26. What is a correct name for the following compound? D) 3,5-Dimethyl-7-heptanol E) 3,5-Dimethyl-1-heptanol 33. Isopentyl is the common name for which alkyl group? A) CH3CH2CH2CHA) 3-Isobutyl-2-methylheptaneB) 3-sec-Butyl-2-methyloctane CH3C) 5-Isobutyl-6-methylheptane B) CH3CH2CHCH2D) 2-Ethyl-3-isopropyloctane CH3E) 4-Isopropyl-3-methylnonane C) CH3CHCH2CH228. What is the correct IUPAC name for the following compound? CH3 D) CH3CH2CH HO CH2CH3A) 3-Hydroxymethylheptane E) CH3B) 3-HydroxymethylhexaneC) 3-Methyloxyheptane CH3CCH2D) 2-Ethyl-1-hexanol CH3E) 2-Ethyl-1-heptanol 34.30. Which of these is the common name for the 1,1-dimethylpropyl group*?A) tert-Butyl B) tert-Pentyl C) IsopentylD) Neopentyl An IUPAC name for is: E) sec-Pentyl A) 3-Isobutyl-2,4-dimethylhexane B) 3-sec-Butyl-2,5-dimethylhexane C) 4-sec-Butyl-2,5-dimethylhexane D) 4-Isopropyl-2,5-dimethylheptane E) 4-Isopropyl-3,6-dimethylheptane 91 92
  4. 4. Chapter 4 Chapter 435. An IUPAC name for the following compound is: Topic: Conformational Analysis 40. The least stable conformation of butane is: H H H H3C H H H CH3A) 4-Isobutyl-3,4-dimethylheptane H CH3 H3C H H CH3 H3C HB) 4-sec-Butyl-2,4-dimethylheptane H HC) 2,4,5-Trimethyl-4-propylheptaneD) 3,4,6-Trimethyl-4-propylheptane I II IIIE) 4-Isobutyl-4,5-dimethylheptane H CH3 H CH3 H CH336. What is the correct IUPAC name for the following compound? H CH3 H H H H HO IV VA) 3-Hydroxymethyl-2-heptene A) IB) 2-(1-methylethyl)-4-hexen-1-ol B) IIC) 5-(1-methylethyl)-2-hexen-6-ol C) IIID) 5-isopropyl-2,6-hexenol D) IVE) 2-(1-methylethyl)-4-hepten-1-ol E) V37. What is the correct IUPAC name for the following compound? 41. The preferred conformation of cis-3-tert-butyl-1-methylcyclohexane is the one in which: OH A) the tert-butyl group is axial and the methyl group is equatorial. B) the methyl group is axial and the tert-butyl group is equatorial. F C) both groups are axial.A) 5-Ethyl-3-fluorohexanol D) both groups are equatorial.B) 5-Ethyl-3-fluoro-1-hexanol E) the molecule exists in a boat conformation.C) 2-Ethyl-4-fluoro-6-hexanolD) 3-fluoro-5-methyl-7-heptanol 42. What structure represents the most stable conformation of cis-1,3-dimethylcyclohexane?E) 3-fluoro-5-methyl-1-heptanol CH3 H CH3 H H CH3 CH3 H38. A correct name for the following compound is: H3C H3C H H I II III ClA) 3-chloro-8-methylbicyclo[4.3.0]nonane H HB) 8-Methyl-3-chlorobicyclo[4.3.1]nonane CH3 CH3C) 3-Methyl-7-chlorobicyclo[4.3.0]nonane H3C H3CD) 3-Methyl-7-chlorobicyclo[4.3.1]decane H HE) 3-chloro-8-methyl[4.3.0]bicyclononane IV V A) I B) II C) III D) IV E) V 93 94
  5. 5. Chapter 4 Chapter 4Topic: Ring Strain 41-47 46. Which is the most stable conformation of cyclohexane? A) Chair 43. Which cycloalkane has the largest heat of combustion per CH2 group*? B) Twist C) Boat D) One-half chair E) Staggered I II III 47. Which cycloalkane has the greatest ring strain? A) Cyclopropane B) Cyclobutane C) Cyclopentane IV V D) Cyclohexane A) I E) Cycloheptane B) II C) III Topic: Conformational Analysis D) IV E) V 48. The most stable conformation of butane is: H H H CH3 H 44. Which cycloalkane has the lowest heat of combustion per CH2 group*? H3C H H H CH3 H CH3 H CH3 H CH3 H H H 3C H H CH3 H 3C H H CH3 H H H H I II III I II III IV V A) I B) II C) III D) IV IV V E) V A) I B) II 49. The most stable conformation of 1,2-dibromoethane is: C) III H H H Br H Br D) IV Br H H H Br H Br H E) V Br H Br Br H H H H H Br H Br 45. Which isomer would have the largest heat of combustion*? H H H H A) Propylcyclopropane I II III IV V B) Ethylcyclobutane A) I C) Methylcyclopentane B) II D) Cyclohexane C) III E) Since they are all isomers, all would have the same heat of combustion. D) IV E) V 95 96
  6. 6. Chapter 4 Chapter 450. The most stable conformation of 2,3-dibromobutane, viewed through the C-2—C-3 52. The most stable conformation of 3-bromo-2-methylpentane, viewed through the bond : C-2—C-3 bond (i.e., C-2 in the front, C-3 in the back): CH3 H H Br H H3C Br H H H Br H CH3 H H Br Br H3C Br Br H H3C Br CH3 CH3 H H CH3 Br CH3 H CH3 H3C CH2CH3 I II III CH3 CH(CH3)2 Br Br I II III H3C H H Br CH3 CH3 Br CH2CH3 Br H H3C H H3C H Br CH3 H CH3 H CH3 IV V H CH2CH3 IV VA) IB) II A) IC) III B) IID) IV C) IIIE) V D) IV E) V51. The most stable conformation of 3-bromo-2-methylpentane, viewed through the C-3—C-4 bond (i.e., C-3 in the front, C-4 in the back): 53. The most stable conformation of 2,3-dimethylpentane, viewed through the CH3 H C-2—C-3 bond (i.e., C-2 in the front, C-3 in the back): Br CH3 CH3 Br H H H Br CH3 H CH3 H H CH3 H H CH3 H H H CH(CH3)2 CH3 CH2CH3 H CH2CH3 H H H CH(CH3)2 CH(CH3)2 H3C H CH3 CH(CH3)2 I II III I II III H CH3 Br H CH3 CH3 Br CH(CH3)2 H CH3 H3C H H CH3 H CH3 H3CH2C H H CH3 H CH2CH3 CH3 CH(CH3)2 IV VA) I IV VB) II A) IC) IIID) IV B) II C) IIIE) V D) IV E) V 97 98
  7. 7. Chapter 4 Chapter 4Topic: Ring Strain 59. The most stable conformation for 1,2-ethanediol (ethylene glycol) is shown below. It is the most stable conformation because: 54. Which cycloalkane has the least ring strain? H A) Cyclopropane H OH B) Cyclobutane C) Cyclopentane H OH D) Cyclohexane H E) Cycloheptane A) this corresponds to an anti conformation. B) in general, gauche conformations possess the minimum energy.Topic: Conformational Analysis C) it is stabilized by intramolecular hydrogen bonding. D) it is a staggered conformation. 55. The most stable conformation of cis-1-tert-butyl-2-methylcyclohexane is the one in E) it has the highest energy of all the possibilities. which: A) the tert-butyl group is axial and the methyl group is equatorial. 60. The graph below is a plot of the relative energies of the various conformations of: B) the methyl group is axial and the tert-butyl group is equatorial. Relative energy C) both groups are axial. D) both groups are equatorial. E) the twist boat conformation is adopted. 56. The most stable conformation of trans-1-tert-butyl-2-methylcyclohexane is the one in which: A) the tert-butyl group is axial and the methyl group is equatorial. 0o 60o 120o 180o 240o 300o 360o B) the methyl group is axial and the tert-butyl group is equatorial. Angle of rotation C) both groups are axial. A) Ethane D) both groups are equatorial. B) Propane E) the molecule is in the half chair conformation. C) Chloroethane D) 1-Chloropropane (C1-C2 rotation) 57. The most stable conformation of trans-1-tert-butyl-3-methylcyclohexane is the one in E) Butane (C1-C2 rotation) which: A) the tert-butyl group is axial and the methyl group is equatorial. 61. The graph below is a plot of the relative energies of the various conformations of: B) the methyl group is axial and the tert-butyl group is equatorial. C) both groups are axial. Relative energy D) both groups are equatorial. E) the twist boat conformation is adopted. 58. In the most stable conformation of cis-1,4-dimethylcyclohexane, the methyl groups are: A) one axial, one equatorial. B) both axial. C) both equatorial. 0o 60o 120o 180o 240o 300o 360o D) alternating between being both axial and both equatorial. Angle of rotation E) None of the above A) 2-chloropropane B) 1,3-dichloropropane C) 2-methylpropane D) Butane (C1-C2 rotation) E) Butane (C2-C3 rotation) Ans: E 99 100
  8. 8. Chapter 4 Chapter 4 Topic: Conformational Analysis62. Consider the graph below, which is a plot of the relative energies of the various conformations of hexane, viewed through the C2-C3 bond. The conformations 64. Which conformation of trans-1-isopropyl-3-methylcyclohexane would be present in corresponding to the 60o and 300o are: greatest amount at equilibrium? A) The conformation with the methyl group equatorial and the isopropyl group axial Relative energy B) The conformation with the methyl group axial and the isopropyl group equatorial C) The conformation with both groups axial D) The conformation with both groups equatorial E) The twist boat conformation. 65. Which conformation represents the most stable conformation of trans-1-bromo-4- methylcyclohexane? 0o 60o 120o 180o 240o 300o 360o Angle of rotation CH3 BrA) Eclipsed CH3 Br Br Br H3C BrB) Staggered, and gauche CH3 CH3C) Staggered and anti I II III IV VD) More stable than the conformation at 180oE) None of the above A) I B) II C) III D) IV63. Consider the graph below, which is a plot of the relative energies of the various E) V conformations of 2,3-dimethylbutane, viewed through the C2-C3 bond. The conformations corresponding to the 120o and 240o are: Topic: Cis-Trans Isomers Relative energy 66. Which of the following can be described as cis isomers? CH3 Br Cl CH3 HO Br HO CH2CH3 CH3 F I II III IV V 0o 60o 120o 180o 240o 300o 360o A) I Angle of rotation B) II, VA) Eclipsed, more stable than the conformation at 0o C) III, IVB) Eclipsed, more stable than the conformation at 180o D) I, III and IVC) Staggered, more stable than the conformation at 0o E) None of the above are cis isomers.D) Staggered, less stable than the conformation at 180oE) Two of the above are true 101 102
  9. 9. Chapter 4 Chapter 4 67. Which of the following can be described as trans isomers? Topic: Conformational Analysis CH3 71. The twist boat conformation is the preferred conformation for this compound. Br Cl CH3 HO Br A) cis-1,4-Di-tert-butylcyclohexane HO CH2CH3 CH3 F B) trans-1,4-Di-tert-butylcyclohexane I II III IV V C) cis-1,3-Di-tert-butylcyclohexane D) trans-1,2-Di-tert-butylcyclohexane E) None of these A) I B) II, V Topic: Ring Strain C) III, IV 72. Which of these C10H18 isomers is predicted to be the most stable? D) I, III and IV H H E) None of the above are trans isomers.Topic: Conformational Analysis H H I II III IV V 68. Which of the following will have the same energy after undergoing ring flip? A) I B) II CH2CH3 OH CH3 C) III HO Cl Br HO CH2CH3 D) IV CH3 F E) V I II III IV V Ans: E A) I B) II Topic: General C) III D) IV 75. How many constitutional isomers are possible for the formula C6H14? E) V. A) 2 B) 3 69. The least stable conformation of cyclohexane is the: C) 4 A) boat. D) 5 B) twist boat. E) 6 C) chair. D) half-chair. 76. How many compounds with the formula C7H16 (heptanes) contain a single 3° carbon E) twist chair. atom? A) 2 70. Express, quantitatively, the difference in stability of the two structures shown below. B) 3 CH3 C) 4 CH3 H3C D) 5 H3C E) 6 I II A) I is more stable than II by 7.5 kJ mol-1. B) I is more stable than II by 15 kJ mol-1. C) II is more stable than I by 7.5 kJ mol-1. D) II is more stable than I by 15 kJ mol-1. E) The two are equal in stability. 103 104
  10. 10. Chapter 4 Chapter 4Topic: Alkane Synthesis, Nomenclature SHORT ANSWER QUESTIONS 77. Catalytic hydrogenation of which of the following will yield 2-methylpentane? A) 2-methyl-1-pentene 2 Topic: Nomenclature B) 2-methyl-2-pentene C) 4-methyl-2-pentene 92. Give the IUPAC name corresponding to the following structure. D) 4-methyl-1-pentene Br E) All of the above OHTopic: Alkane Synthesis, Nomenclature 78. The synthesis of an alkyne precursor to 2,2-dimethylheptane is accomplished most 93. Give the IUPAC name corresponding to the following structure: effectively by the reaction between these two reagents: Br A) CH3CH2CH2C!CNa and (CH3)3CBr HO B) CH3CH2C!CNa and (CH3)3CCH2Br C) (CH3)3CC!CNa and CH3CH2CH2Br D) (CH3)3CCH2CH2C!CH and CH3CH2I 94. Give the IUPAC name corresponding to the following structure: Br E) HC!CNa and (CH3)3CCH2CH2Br F 79. The reaction of the Na salt of 3-methyl-1-pentyne with 1-bromo-3-methylbutane produces which of these? 95. Give the IUPAC name corresponding to the following structure: A) 3,8-dimethyl-4-nonyne B) 2,7-dimethyl-4-nonyne C) 3,8-dimethyl-5-nonyne HO D) 3,7-dimethyl-4-nonyne E) 3,7-dimethyl-5-nonyneTopic: General 96. Draw the bond-line structural formula corresponding to the most stable conformation of the following substance: trans-1-bromo-3-(1-methylpropyl)cyclohexane 80. What is the simplest alkane, i.e., the one with the smallest molecular weight, which possesses primary, secondary and tertiary carbon atoms? A) 2-Methylpropane 97. Draw the bond-line structural formula corresponding to the name: 2,5,9-trimethyl-2- B) 2-Methylbutane decen-7-yne C) 2-Methylpentane D) 3-Methylpentane Topic: Alkane Conformations E) 2,2-Dimethylbutane 98. Draw the Newman projection formula for the gauche conformation of the C2-C3 bond in pentane. 81. How many alkanes of formula C7H16 possess a quaternary carbon atom? A) 1 99. Draw the Newman projection formula for the most stable conformation of the C2-C3 B) 2 bond in 3-methylpentane. C) 3 D) 4 E) 5 105 106
  11. 11. Chapter 4 Chapter 4Svar Test banken Solomons Chapt. 4 92. 5-bromo-6-cyclopentyl-2-hexanolFråga Svar Rätt/Fel Fråga Svar Rätt/Fel 93. 3-(2-bromobutyl)cyclopentanol 1 C 41 D trans-1-bromo-2-fluorocyclohexane 2 D 42 B 94. 95. 3-ethyl-6,7-dimethyl-2-octanol 3 E 43 A 4 D 44 D 96: Br 5 E 45 A 6 C 46 A 97: 7 D 47 A 8 D 48 C 9 A 49 C 10 A 50 C 98: CH3 11 D 51 A H CH2CH3 12 A 52 E 13 C 53 D H H 14 A 54 D H 15 D 55 B 99: CH3 16 E 56 D H CH3 17 A 57 B 18 D 58 A H H 19 A 59 C CH2CH3 20 A 60 D 21 D 61 E 22 C 62 B 23 C 63 A 24 C 64 B 25 B 65 A 26 E 66 B 27 C 67 C 28 D 68 E 29 E 69 D 30 B 70 A 31 E 71 A 32 E 72 E 33 C 73 A 34 D 74 A 35 C 75 D 36 B 76 C 37 E 77 E 38 A 78 C 39 E 79 A 40 B 80 B 81 C 107 108
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