Chapter 12 Introduction To Organic Chemistry: Hydrocarbons

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Chapter 12 – Introduction to Organic Chemistry: HydrocarbonsSection 12.1 – AlkanesGoal: Identify properties characteristic of organic or inorganic compounds.Summary:Organic compounds: always contain carbon and hydrogen (thought sometimes other nonmetals as well.)Inorganic compounds: all other compounds. Often ionic (metal nonmetal)Organic compoundsCovalent bondsMost form nonpolar moleculesLow melting and boiling pointsNot very soluble in waterDissolve as molecules in solutions (not ions)Burn vigorously in airInorganic compoundsOften ionic or contain polar covalent bondsUsually soluble in waterHigh melting and boiling pointsMost are soluble, unless nonpolarProduce ions in waterDo not burn in airEach carbon atom covalently bonds 4 times (due to its 4 valence electrons). When 4 individual groups areattached to a carbon, it has a tetrahedral geometry.

Practice Problems1. Identify each the following as a formula of an organic or inorganic compound:a. KClb. C4H10c. C2H6Od. H2SO4e. CaCl2f. C3H7Cl2. Identify each of the following as a formula of an organic or inorganic compound:a. C6H12O6b. K3PO4c. I2d. C2H6Se. C10H22f. C4H9Br3. Identify each of the following properties as more typical of an organic or inorganic compound:a. is soluble in waterb. has a low boiling pointc. contains carbon and hydrogend. contains ionic bonds4. Identify each of the following properties as more typical of an organic or inorganic compound:a. contains Li and Fb. is a gas at room temperaturec. contains covalent bondsd. produces ions in water5. In a propane molecule with three carbon atoms, what is the shape around each carbon? (carbon is black,hydrogen is white)a. trigonal planarb. tetrahedralc. square planard. trigonal bipyramidale. linear

Section 12.2 – AlkanesGoal: Write the IUPAC names and draw the condensed or line-angle structural formulas for alkanes andcycloalkanes.Summary:Alkanes: a type of hydrocarbon in which the carbon atoms are connected on by single bonds.To name alkanes (no substituents), “[prefix]ane”The prefix refers to the number of carbons in the chain:meth (1), eth (2), prop (3), but (4), pent (5), hex (6), hept (7), oct (8), non (9), dec (10)If the carbon chain is connected in a ring, use “cyclo” at the beginning of the name (before the prefix)Example name the following:Solution: An alkane with a give-carbon chain is name with the prefix pent followed by ane, which is pentaneThere are several ways to draw molecules. The following two ways are simplified forms that make life easierand drawing quicker. Note in the line-angle form, the carbons are at each end of a line and the hydrogens areassumed. (There’s always enough H’s to give each C 4 bonds.)Practice Problems6. Give the IUPAC name for the following alkane or cycloalkane: (carbon black, hydrogen white)a. hexaneb. pentanec. butaned. cyclobutanee. cyclopentane7. Give the IUPAC name for the following alkane or cycloalkane:a. methaneb. methenec. ethaned. octanee. propane

8. Give the IUPAC name for the following alkane or cycloalkane:a. hexeneb. butanec. pentaned. hexanee. heptane9. Give the IUPAC name for the following alkane or cycloalkane:a. cycloheptaneb. octanec. cyclohexaned. heptanee. 2-cyclohexane10. Give the IUPAC name for the following alkane or cycloalkane:a. oneaneb. butanec. propaned. ethanee. methane11. Give the IUPAC name for the following alkane or cycloalkane: (black carbon, white hydrogen)a. pentaneb. methanec. butaned. propanee. ethane12. Give the IUPAC name for the following alkane or cycloalkane:a. nonaneb. propanec. octaned. heptanee. hexane13. Give the IUPAC name for the following alkane or cycloalkane:a. decaneb. nonanec. octaned. heptanee. hexane14. Draw the condensed structural formula of: methane.a. CH3b. CH4c. CH3-CH3d. CH3-CH2-CH3e. CH3-CH2-CH2-CH3

25. Indicate whether the following pair represents structural isomers or the same molecule:26. Indicate whether the following pair represents structural isomers or the same molecule:27. Give the IUPAC name for the following:a. pentaneb. 2-methylbutanec. 2-ethylpropaned. 2,2-dimethylpropanee. 2,2,2-trimethylethane28. Give the IUPAC name for the following:a. 2,3-dimethylpentanb. 1,1,2-trimethylbutanec. 3,4-dimethylpentaned. dimethylpentanee. 2-isopropylbutane29. Give the IUPAC name for the following:a. 2,6-diethyl-4-tert-butylheptaneb. 4-isopropyl-2,6-dimethylheptanec. 4-butane-2,6-methylheptaned. 3-isobutyl-2,2,6-trimethylhexanee. 4-tert-butyl-2,6-dimethylheptane30. Give the IUPAC name for the following:a. cyclopentaneb. methylcyclobutanec. ethylcyclobutaned. 1-ethylcyclobutanee. 1-methylcyclobutane31. Give the IUPAC name for the following:a. 1-chloro-3-bromocyclohexaneb. 1-bromo-3-chlorocyclohexanec. 1-chloro-3-bromohexaned. 1-bromo-3-chlorocycloheptanee. 1-bromo-3-chlorohexane

32. Give the IUPAC name for the following:a. 2-methylpentaneb. 2-methylpentenec. methylpentaned. 4-methylpentanee. 1,1-dimethylbutane33. Give the IUPAC name for the following:a. 3-methyl-4-pentyloctaneb. 5-pentyl-6-methyloctanec. 5-sec-butyldecaned. sec-butyldecanee. 6-sec-butyldecane34. Give the IUPAC name for the following:a. 3,4-diethylhexaneb. 3,4-dimethylpentanec. 3-ethyl-4-ethylhexaned. 3,4-dimethylhexanee. 3,4-diethylheptane35. Give the IUPAC name for the following:a. 2-phenylpentaneb. 2-propylcyclohexanec. isopropylcyclohexaned. propylcyclohexanee. 1-isopropylcyclohexane36. Give the IUPAC name for the following:a. 1,1-dimethylcyclopentaneb. methylcycloheptanec. 2-methylhexaned. 1,1-dimethylpentanee. methylcyclopentane37. Draw the condensed structural formula for the following alkane: 3,3-dimethylpentane38. Draw the condensed structural formula for the following alkane: 2,3,5-trimethylhexane39. Draw the condensed structural formula for the following alkane: 3-ethyl-5-isopropyloctane40. Draw the condensed structural formula for the following alkane: 1-bromo-2-chloroethane

41. Draw the condensed structural formula for the following alkane: 3-ethylpentane42. Draw the condensed structural formula for the following alkane: 4-isopropyl-3-methylheptane43. Draw the condensed structural formula for the following alkane: 4-ethyl-2,2-dimethyloctane44. Draw the condensed structural formula for the following alkane: 2-bromopropane.45. Draw the line-angle structural formula for the following: 3-methylheptane46. Draw the line-angle structural formula for the following: 1-chloro-3-ethylcyclopentane47. Draw the line-angle structural formula for the following: bromocylobutane48. Draw the line-angle structural formula for the following: 2,3-dichlorohexane49. Draw the line-angle structural formula for the following: 1-bromo-2-methylpentane50. Draw the line-angle structural formula for the following: 1,2,3-trimethylchlopropane51. Draw the line-angle structural formula for the following: ethylcyclohexane

Section 12.4 – Properties of AlkanesGoal: Identify the properties of alkanes and write a balanced chemical equation for combustion.Summary:As carbon chains get longer, the boiling point increases. This is due to increased surface area for two chainsto laying side by side (like spaghetti noodles or licorice) that allows more attractions between the two chains,the stronger the bonds, the higher the temperature has to be to boil.Branched hydrocarbons have less surface area for two molecules to stack against each other for attractions tooccur. For that reason, carbon chains have higher boiling points than branched. Cycloalkanes have higher boiling points because the rings can stack, creating more interactions. Alkanes readily burn in oxygen to produce carbon dioxide, water, and energy. This is combustion:Alkane(g) O2(g) CO2(g) H2O(g) energy Alkanes are nonpolar molecules, are not soluble in water, and usually less dense than water.Practice Problems52. Heptane, used as a solvent for rubber cement, has a density of 0.68g/mL and boils at 98 C.a. Draw the condensed and line-angle structural formulas for heptane.b. Is heptane a solid, liquid, or gas at room temperature?c. Is heptane soluble in water?d. Will heptane float on water or sink?e. Write the balanced chemical equation for the completely combustion of heptane.

53. Nonane has a density of 0.79 g/mL and boils at 151 C.a. Draw the condensed and line-angle structural formulas for nonane.b. Is nonane a solid, liquid, or gas at room temperature?c. Is nonane soluble in water?d. Will nonane float on water or sink?e. Write the balanced chemical equation for the complete combustion of nonane.54. Write the balanced chemical equation for the complete combustion of ethane.a. C2H4 3O2 2CO2 2H2Ob. 2C2H6 7O2 4CO2 6H2Oc. C2H6 7/2 O2 2CO2 3H2Od. C2H4 O2 CO2 H2Oe. C2H6 O2 CO2 H2O55. Write the balanced chemical equation for the complete combustion of cyclopropane.a. C3H8 O2 CO2 H2Ob. C3H8 5O2 3CO2 4H2Oc. 2C3H6 2O2 CO2 3H2Od. C3H6 O2 CO2 H2Oe. 2C3H6 9O2 6CO2 6H2O56. Write the balanced chemical equation for the complete combustion of octane.a. C8H10 O2 CO2 H2Ob. 2C8H18 25O2 16CO2 18H2Oc. C8H18 O2 CO2 H2Od. C8H18 25/2 O2 8CO2 9H2Oe. C8H10 O2 4CO2 5H2O57. Write the balanced chemical equation for the complete combustion of hexane.a. 2C6H14 19O2 12CO2 14H2Ob. C6H14 19/2 O2 6CO2 7H2Oc. C2H6 7/2 O2 2CO2 3H2Od. C2H4 O2 CO2 H2Oe. C2H6 O2 CO2 H2O58. Write the balanced chemical equation for the complete combustion of cyclopentane.a. 2C5H10 15O2 10H2O 10CO2b. C5H10 15/2 O2 5H2O 5CO2c. C5H10 15O2 5H2O 5CO2d. C5H12 8O2 5H2O 6CO2e. C5H12 4O2 5H2O 3CO2

59. Write the balanced chemical equation for the complete combustion of butane.a. C4H10 13/2 O2 4H2O 5CO2b. C4H10 13 O2 4H2O 5CO2c. 2C4H10 13O2 8H2O 10CO2d. C4H8 6O2 4H2O 4CO2e. C4H8 3O2 2H2O 2CO260. In each of the following pairs of hydrocarbons, which one would you expect to have the higher boilingpoint?a. pentane or heptaneb. propane or cyclopropanec. hexane or 2-methyl pentane61. In each of the following pairs of hydrocarbons, which one would you expect to have the higher boilingpoint?a. propane or butaneb. hexane or cyclohexanec. 2,2-dimethylpentane or heptane

Section 12.5 – Alkenes and AlkynesGoal: Identify structural formulas as alkenes, cycloalkenes, and alkynes, and write their IUPAC names.Summary:Alkenes are hydrocarbons with at least one double bond.Alkynes are hydrocarbons with at least one triple bond.The IUPAC names for alkenes end with ene, while alkyne names end with yne.The main carbon chain is numbered from the end nearest to the double or triple bond.Example – Naming alkenes and alkynesWrite the IUPAC names for the following:SolutionStep 1: Name the longest carbon chain that contains the double or triple bond.6 carbons with double bond – hexane6 carbons with triple bond – hexyneStep 2: Number the carbon chain, starting from the end nearer the double or triple bond.13554242-hexene32162-hexyneStep 3: Give the location and name of each substituent (in alphabetical order) as a prefix to the alkene or alkynename.5135432 16244-methyl-2-pentene2-hexyne (no substituents)Example – naming cycloalkenesIf no substituents (other than one double bond) do not include numbering (unnecessarily)If there are substituents, begin numbering with 1 and 2 as the double bond. Then move clockwise orcounterclockwise, whichever direction meets the next substituents first.Cyclohexene3,3-dimethylcyclopentene

62. Give the IUPAC name for the following:a. 2-methyl-1-propaneb. isopropylethenec. methened. butenee. 2-methyl-1-propene63. Give the IUPAC name for the following:a. 4-bromo-4-methyl-2-butyneb. 2-bromo-3-pentynec. bromopentyned. 4-bromo-2-pentynee. 1-bromo-1methyl-2-butene64. Give the IUPAC name for the following:a. 4-ethyl-cyclopenteneb. ethylcyclobutenec. 4-ethylcyclobutened. 4-ethylcyclopentanee. 4-methyl-cyclopentene65. Give the IUPAC name for the following:a. ethylhexeneb. 3-ethyl-4-hexenec. 4-propyl-2-hexened. 4,4-diethyl-2-butenee. 4-ethyl-2-hexene66. Give the IUPAC name for the following:a. 5-hexeneb. 5-heptenec. 1-hexened. 1-hexanee. 1-heptene67. Give the IUPAC name for the following:a. 6-methyl-2-heptyneb. methylhexynec. 2-ethyl-5-hexyned. 6-methyl-2-heptenee. 2-methyl-6-heptyne68. Give the IUPAC name for the following:a. 1,4-dimethylcyclohexyneb. 2,5-diethylcycloheptenec. 1,4-dimethylcyclohexened. 2,4-diethylcycloheptenee. 2,5-dimethylcyclohexene

69. Give the IUPAC name for the following:a. dichlorohexeneb. 4,6-dichloro-1-heptenec. chloroheptaned. 4,6-dichloro-6-methyl-1-hexenee. 2,4-dichloro-6-heptene70. Draw the condensed structural formula of: 1-pentene71. Draw the condensed structural formula of: 2-methyl-1-butene72. Draw the line-angle structural formula of: 3-methylcyclohexene73. Draw the line-angle structural formula of: 1-chloro-3-hexyne74. Draw the condensed structural formula of: 3-methyl-1-butyne75. Draw the condensed structural formula of: 3,4-dimethyl-1-pentene76. Draw the line-angle structural formula of: 1,2-dichlorocyclopentene77. Draw the line-angle structural formula of: 2-methyl-2-hexene

Section 12.6 – Cis-Trans IsomersGoal: Draw the condensed and line-angle structural formulas and give the names for the cis-trans isomers ofalkenes.Summary:Geometric or cis-trans isomers of alkenes occur when the carbon atoms in the double bond are connected todifferent atoms or groups.Practice Problems78. Give the IUPAC name for the following, using cis or trans prefixes:a. trans-2-buteneb. trans-2,3-dimethylethenec. cis-butened. cis-2-butenee. cis-2,3-dimthylethene79. Give the IUPAC name for the following, using cis or trans prefixes:a. trans-3-octeneb. trans-5-octenec. cis-5-octened. cis-1-ethyl-2-butylethenee. cis-3-octene80. Give the IUPAC name for the following, using cis or trans prefixes:a. cis-hepteneb. cis-4-heptenec. trans-4-heptened. cis-3-heptenee. trans-3-heptene81. Give the IUPAC name for the following, using cis or trans prefixes:a. trans-1-methyl-2-ethyletheneb. cis-1-methyl-2-ethylethenec. 2-pentened. cis-2-pentenee. trans-2-pentene

82. Give the IUPAC name for the following, using cis or trans prefixes:a. cis-2-hepteneb. trans-2-heptenec. cis-1-butyl-2-methylthened. trans-1-butyl-2-methylethenee. 2-heptene83. Give the IUPAC name for the following, using cis or trans prefixes:a. cis-4-hepteneb. trans-4-heptenec. trans-3-heptened. cis-3-heptenee. 3-heptene84. Draw the condensed structural formula for: cis-1,2-difluoroethene85. Draw the condensed structural formula for: trans-1-bromo-2-chloroethene86. Draw the condensed structural formula for: cis-2-hexene87. Draw the condensed structural formula for: trans-3-heptene88. Draw the condensed structural formula for: trans-2-pentene89. Draw the condensed structural formula for: cis-4-octene90. Which of the following cannot have cis-trans isomers? (Select all that apply)91. Which of the following cannot have cis-trans isomers? (Select all that apply)

12.7 – Addition Reactions for AlkenesGoal: Draw the condensed or line-angle structural formulas and give the names for the organic products ofaddition reactions of alkenes. Draw a condensed structural formula for a section of a polymer.Summary:The addition of small molecules to the double bond is a characteristic reaction of alkenes.Hydrogenation adds hydrogen atoms to the double bond of an alkene to yield an alkane.Hydration adds water to a double bond fo an alkene to form an alcohol. The H is added to the C with more H’s already attached to it. (Markovnikov’s Rule)Polymers are long-chain molecules that consist of many repeating units of smaller carbon molecules calledmonomers. Many synthetic materials are made using addition reactions in which a catalyst links the carbon atomsfrom various kinds of alkene molecules (the monomers). The name of a polymer is that name of the monomers with “poly” in front. (See equation below.)Understanding the ConceptsWhat is a polymer?What is a monomer?Write an equation that represents the formation of a portion of polypropylene (polypropene) from three of itsmonomers.

Practice Problems92. Draw the structural formula for the product in each of the following reactions using Markovnikov’s rulewhen necessary:93. Draw the structural formula for the product in each of the following reactions using Markovnikov’s rulewhen necessary:94. Write an equation that represents the formation of a portion of polystyrene from three of its monomers.95. The plastic polyvinylidene difluoride, PVDF, is made form monomers of 1,1-difluoroethene. Draw theexpanded structural formula for a portion of the polymer formed from three monomers of 1,1difluoroethene.96. The polymer polyacrylonitrile, PAN, used in the fabric material. Orlon is made from monomers ofacrylonitrile. Draw the expanded structural formula for a portion of the polymer formed from threemonomers of acrylontirile.

Section 12.8 – Aromatic CompoundsGoal: Describe the bonding in benzene; name aromatic compounds, and draw their line-angle structuralformulas.Summary:Aromatic compounds are molecules that contain benzene, C6H6, a cyclic structure containing six carbon atomsand six hydrogen atoms. The structure of benzene is represented as a hexagon with a circle in the center (far right in image). The IUPAC system uses the names of benzene, toluene, aniline, and phenol. In the IUPAC name, two or more substituents are numbered and listed in alphabetical order. (The samenaming scheme as with other rings.) When a benzene is used as a substituent on a carbon chain, it is called a phenyl group:

Practice Problems97. Give the IUPAC name for each of the following:98. Give the IUPAC name for each of the following:99. Draw the structural formula for each of the following:a. 1-bromo-3-chlorobenzeneb. 1-ethyl-4-methylbenzenec. Propylbenzened. 1,2,4-trichlorobenzene

Section 12.2 – Alkanes Goal: Write the IUPAC names and draw the condensed or line-angle structural formulas for alkanes and cycloalkanes. Summary: Alkanes: a type of hydrocarbon in which the carbon atoms are connected on by single bonds. To name alkanes “(no substituents), [prefix]ane” The prefix refers to the number of carbons in the chain: .

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