Chap010

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Wilfrid Laurier University *

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Chemistry

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Feb 20, 2024

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Chapter 10 - An Introduction to Organic Chemistry - The ... Chapter 10 An Introduction to Organic Chemistry - The ... Short Answer Questions 1. Draw the structural formula of n-propane. 2. Name three allotropic forms of carbon. buckminsterfullerene, graphite and diamond 3. What allotrope of carbon has a 3-dimensional network structure? diamond 4. What are the three families of aliphatic hydrocarbons? alkanes, alkenes and alkynes 5. Name the heteroatom in an ether. oxygen 6. Name the functional group found in all aldehydes. carbonyl group 10-1

Chapter 10 - An Introduction to Organic Chemistry - The ... 10-2

Chapter 10 - An Introduction to Organic Chemistry - The ... 7. Name the family of organic compounds that contain a hydroxyl group. alcohols 8. Name the family of organic compounds that contain an alkoxy group. ethers 9. Name the two families of organic compounds that contain a carbonyl group. aldehydes and ketones 10. Draw the structure of the alkoxy functional group found in ethers. 11. Draw the structure of the carboxyl functional group found in carboxylic acids. 12. Name the functional groups shown below. carboxyl; hydroxyl 10-3

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Chapter 10 - An Introduction to Organic Chemistry - The ... 10-4

Chapter 10 - An Introduction to Organic Chemistry - The ... 13. A waxy alkane consists of molecules containing 25 carbon atoms each. How many hydrogen atoms are in one of these molecules? 52 14. Which kind of formula for organic compounds explicitly shows all of the atoms and bonds in a molecule? structural formula 15. In one word, describe the geometry around a carbon atom which has four single bonds to neighboring atoms. What is the angle between any two of these bond directions? tetrahedral; 109.5 ° 16. Write the structural formula of 2,2-dimethylhexane. 17. How does an alkyl group differ from its parent alkane? The alkyl group has one less hydrogen atom. 18. What is meant by a "secondary" alkyl group? The carbon atom which is the point of attachment of the alkyl group is bonded to two other carbon atoms and one hydrogen atom. 10-5

Chapter 10 - An Introduction to Organic Chemistry - The ... 19. What are the I.U.P.A.C. and common names for CHCl 3 ? trichloromethane; chloroform 20. What is the molecular formula of dichloromethane? CH 2 Cl 2 21. Draw the structure of 1-chloro-3-methylbutane. 22. What is the molecular formula of the simplest alkane capable of having constitutional isomers? C 4 H 10 23. Draw carbon skeletons to show the three isomers of pentane, C 5 H 12 . 24. What is the term for compounds that have the same molecular formula, but have different structures? (constitutional) isomers 10-6

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Chapter 10 - An Introduction to Organic Chemistry - The ... 10-7

Chapter 10 - An Introduction to Organic Chemistry - The ... 25. A cycloalkane molecule contains 8 carbon atoms. How many hydrogen atoms are in the molecule? 16 26. How does the formula of a cycloalkane differ from that of the corresponding alkane? The cycloalkane has two fewer hydrogen atoms in its formula. 27. Name the compound. trans -1,3-dimethylcyclohexane 28. Draw the structure of trans -1,3-dibromocyclopentane. 29. Draw all three isomers of dichlorocyclopropane. 10-8

Chapter 10 - An Introduction to Organic Chemistry - The ... 30. What is the term used to describe the various arrangements of a molecule that are capable of rapid interconversions by simple rotation about a bond? conformations or conformers 31. How do the different conformations of an alkane molecule arise? through rotation about C C single bonds 32. Draw line formulas to show the chair and boat conformations of cyclohexane. Which conformation is more stable and why? The chair conformation is more stable. In this arrangement, the hydrogen atoms are all staggered and the bond angles at the carbon atoms achieve the ideal tetrahedral values of 109.5 ° . 33. Explain what is meant by "staggered" hydrogen atoms, when describing the conformation of an alkane molecule. When rotation around a carbon-carbon single bond takes the hydrogen atoms on the two carbons as far away from each other as possible, the conformation is "staggered". This conformation is more stable than when the hydrogens are closer together. 34. What conditions are necessary in order for methane to react with chlorine? light or high temperature 10-9

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Chapter 10 - An Introduction to Organic Chemistry - The ... 35. What is the term used to describe organic reactions in which an atom in a molecule is replaced by a new atom? substitution 36. Write a balanced equation for the monochlorination of butane, C 4 H 10 . C 4 H 10 + Cl 2 ® C 4 H 9 Cl + HCl Multiple Choice Questions 37. Diamond and graphite are both ___________ of carbon. A. Isotopes B. Isomers C. Allotropes D. Aldehydes E. Both A and B 38. What type(s) of carbon-carbon bonds are never found in a saturated hydrocarbon? A. Single bonds B. Single and double bonds C. Double and triple bonds D. Single, double and triple bonds E. None of the above 39. Name the functional group found in all alcohols. A. Oxygen B. Hydroxyl C. Carbonyl D. Methyl E. None of the above 10-10

Chapter 10 - An Introduction to Organic Chemistry - The ... 40. Name the major family of organic compounds that contain a benzene structure. A. Aliphatic B. Isotopic C. Alkene D. Alkyne E. Aromatic 41. Name the main functional group present in acetone (propanone): A. Hydroxyl group B. Carbonyl group C. Alkoxy group D. Alkene group E. None of the above 42. Name the functional groups shown below. A. Alkoxy group, amine B. Carbonyl, aldehyde C. Hydroxyl group, ammonia D. Carbonyl group, amine E. None of the above 43. What is the molecular formula of butane? A. C 3 H 8 B. C 4 H 8 C. C 4 H 10 D. C 2 H 6 E. None of the above 10-11

Chapter 10 - An Introduction to Organic Chemistry - The ... 44. Which linear alkane contains five carbon atoms? A. Propane B. Butane C. Pentane D. Heptane E. Decane 45. Which of the following is the condensed structural formula of 3-methylheptane. A. CH 3 CH 2 CH(CH 3 )CH 2 CH 2 CH 2 CH 3 B. CH 3 CH 2 CH 2 (CH 3 )CH 2 CH 2 CH 2 CH 3 C. CH 3 CH(CH 3 )CH 2 CH 2 CH 2 CH 2 CH 3 D. CH 3 (CH 3 )CHCH 2 CH 2 CH 2 CH 3 E. None of the above 46. What is the I.U.P.A.C. name of the following compound? A. 2-bromo-2-methylpropane B. 2,2-dibromomethylpropane C. Bromomethylbutane D. 2-bromoisobutane E. 2-methyl-2-bromopropane 47. What is the I.U.P.A.C. name of the following compound? A. 2,4,4-trimethylpentane B. 2,2,4-octane C. 2,2,4-trimethylpentane D. Trimethylpentane E. None of the above 10-12

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Chapter 10 - An Introduction to Organic Chemistry - The ... 48. Which of the following are isomers with the formula C 5 H 12 ? A. CH 3 CH 2 CH 2 CH 2 CH 3 B. CH 3 CHCH 3 CH 2 CH 3 C. D. All of the above E. None of the above 49. Name the compound. A. Methylcyclohexane B. 1-methylcyclohexane C. Toluene D. Benzylmethane E. 1-methylbenzene 50. How many moles of water are produced by the complete combustion of one mole of methane? A. 1 B. 2 C. 3 D. 4 E. 5 51. Which of the following is a balanced equation for the complete combustion of cyclooctane, C 8 H 16 ? A. C 8 H 18 + 12 O 2 ® 8 CO 2 + 9 H 2 O B. C 8 H 16 + O 2 ® CO 2 + H 2 O C. 2 C 8 H 12 + 24 O 2 ® 16 CO 2 + 12 H 2 O D. C 8 H 16 + 12 O 2 ® 8 CO 2 + 8 H 2 O E. All of the above 10-13

Chapter 10 - An Introduction to Organic Chemistry - The ... 52. What important synthesis did Friedrich Wöhler carry out in 1828? A. Ammonium bicarbonate B. Urea C. Ammonium cyanate D. Ammonium chloride E. Ammonium cyanide 53. What is the source of most of the synthetic organic compounds that are used today? A. Methane B. Trees C. Petroleum D. Natural gas E. Coal 54. Which of the following is not a typical property of inorganic compounds? A. High boiling point B. Flammable C. Water-soluble D. Rapid reactions E. High melting point 55. Which of the following is not an aliphatic hydrocarbon? A. Alkene B. Alkyne C. Alkane D. Benzene E. Cycloalkane 56. Which major family of organic compounds contains a benzene ring? A. Alcohol B. Alkyne C. Aliphatic D. Heterocyclic E. Aromatic 10-14

Chapter 10 - An Introduction to Organic Chemistry - The ... 10-15

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Chapter 10 - An Introduction to Organic Chemistry - The ... 57. Which functional group is found in alcohols? A. Alkoxy B. Ether C. Amino D. Carbonyl E. Hydroxyl 58. Identify the functional group present in the molecule shown below. A. Acyl B. Hydroxyl C. Carboxyl D. Carbonyl E. Alkoxy 59. Identify the functional group present in the molecule shown below. A. Acyl B. Hydroxyl C. Carboxyl D. Carbonyl E. Alkoxy 60. Identify the functional group present in the molecule shown below. A. Acyl B. Hydroxyl C. Carboxyl D. Carbonyl E. Alkoxy 10-16

Chapter 10 - An Introduction to Organic Chemistry - The ... 10-17

Chapter 10 - An Introduction to Organic Chemistry - The ... 61. Identify the functional group present in the molecule shown below. A. Amido B. Nitrido C. Amyl D. Amino E. Acyl 62. What word best describes the geometry (shape) around a carbon atom that has four single bonds to neighboring atoms? A. Tetrahedral B. Planar C. Regular D. Linear E. Unsaturated 63. Which of the following molecular formulas is not that of an alkane or cycloalkane? A. C 6 H 6 B. C 6 H 12 C. C 5 H 12 D. C 3 H 6 E. C 3 H 8 64. Which is the correct order of melting points of the following alkanes, from highest temperature to lowest temperature? A. Nonane > hexane > methane > ethane B. Hexane > nonane > ethane > methane C. Nonane > hexane > ethane > methane D. Nonane > ethane > hexane > methane E. Methane > ethane > hexane > nonane 10-18

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Chapter 10 - An Introduction to Organic Chemistry - The ... 65. Name the structure shown below. A. Ethane B. Ether C. Ethereal D. Ethanyl E. Ethyl 66. What is the I.U.P.A.C. name of the following compound? A. 2-chloromethane B. 2-chloropropane C. 1-methyl-1-chloroethane D. 1,1-chloromethylethane E. 2-chloroethane 67. What is the I.U.P.A.C. name of the following compound? A. 2-ethylbutane B. 2-methyl-2-ethylpropane C. 3-methylpentane D. Trimethylpropane E. 2-methyl-diethylmethane 10-19

Chapter 10 - An Introduction to Organic Chemistry - The ... 68. What is the I.U.P.A.C. name of the following compound? A. 3-ethylpentane B. 3-methylheptane C. 1,4-dimethylpentane D. 3-ethylheptane E. 2-methyl-2-ethylbutane 69. What is the I.U.P.A.C. name of the following compound? A. Dibromopentane B. 2,4-dibromopentane C. 2,4-dibromohexane D. 2,5-dibromohexane E. 1-bromo-2,5-methylbromopentane 70. What is the I.U.P.A.C. name of the following compound? A. 2,2-dimethylpropane B. 2-methylbutane C. Dimethylbutane D. 3-methylbutane E. 3-methylpropane 10-20

Chapter 10 - An Introduction to Organic Chemistry - The ... 71. What is the I.U.P.A.C. name of the following compound? A. 2,2-dimethylpropane B. 2-methylbutane C. Dimethylbutane D. Tetramethylethane E. 2,2,2-trimethylmethane 72. What term describes molecules that have the same molecular formula, but have different structures? A. Allotropes B. Isotopes C. Conformers D. Isomers E. Alkanes 73. Which of the following is a correctly named isomer of 2-methylpropane? A. 1-methylpropane B. 2,2-dimethylpropane C. Propane D. Cyclobutane E. Butane 74. Which of the following compounds is a correctly named isomer of pentane? A. 2-ethylpentane B. Isobutylethane C. 2-methylbutane D. 2-methyloctane E. 3-methylbutane 10-21

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Chapter 10 - An Introduction to Organic Chemistry - The ... 75. Which of the following is an isomer of 1,1-dibromoethane? A. Br 2 CHCH 3 B. CH 2 BrCH 2 Br C. CH 3 CHBr 2 D. CHBr 2 CHBr 2 E. CH 3 BrCH 3 Br 76. Which of the following is an isomer of butane? A. Cyclobutane B. CH 3 CH(CH 3 ) 2 C. Benzene D. CH 3 CHBrCH 2 CH 3 E. 2,2-dimethylpropane 77. Of the structures shown below, which two are isomers? A. 1 and 2 B. 1 and 3 C. 1 and 4 D. 2 and 4 E. 3 and 4 78. Of the structures shown below, which of the sets are not isomers? A. 1 and 2 B. 1 and 3 C. 1 and 4 D. 1, 3 and 4 E. 3 and 4 10-22

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Chapter 10 - An Introduction to Organic Chemistry - The ... 79. How many moles of carbon dioxide are formed in the complete combustion of one mole of octane, C 8 H 18 ? A. 2 B. 4 C. 8 D. 17 E. 26 80. Which equation correctly represents the complete combustion of propane, C 3 H 8 ? A. C 3 H 8 + 7O 2 ® 3CO 2 + 8H 2 O B. C 3 H 8 + 5O 2 ® 3CO 2 + 4H 2 O C. C 3 H 8 + 10O ® 3CO 2 + 4H 2 O D. C 3 H 8 + 7O ® 3CO + 4H 2 O E. 2C 3 H 8 + 7O 2 ® 6CO + 8H 2 O True / False Questions 81. Urea is an isomer of ammonium cyanate. TRUE 82. In a solution of water, inorganic compounds tend to be better conductors of electricity than organic compounds. TRUE 83. Organic compounds tend to have higher boiling points than inorganic compounds. FALSE 84. Organic compounds tend to be more soluble in hexane than inorganic compounds. TRUE 10-23

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Chapter 10 - An Introduction to Organic Chemistry - The ... 85. The carboxyl functional group is found in all ketones. FALSE 86. Alkanes are more soluble in water than in nonpolar solvents. FALSE 87. The condensed formula of a compound conveys the same information as the structural formula, but in a more concise form. TRUE 88. The n-propyl group is CH 3 CH 2 CH 2 -. TRUE 89. There is only one stable alkane of formula C 4 H 10 . FALSE 90. 2-Methylhexane is an isomer of hexane. FALSE 91. The chair and boat conformations of cyclohexane are isomers of each other. FALSE 92. The chair conformation of cyclohexane is more stable than the boat conformation. TRUE 93. Carbon monoxide may be produced in the partial (incomplete) combustion of methane. TRUE 10-24

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Chapter 10 - An Introduction to Organic Chemistry - The ... 10-25

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Chapter 10 - An Introduction to Organic Chemistry - The ... 94. All polyhalogenated compounds are environmentally safe as they break down rapidly to harmless products. FALSE 95. The common name of dichloromethane is methylene chloride. FALSE 10-26

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