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1 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu How to Use This Presentation To View the presentation as a slideshow with effects select “View” on the menu bar and click on “Slide Show.” To advance through the presentation, click the right-arrow key or the space bar. From the resources slide, click on any resource to see a presentation for that resource. From the Chapter menu screen click on any lesson to go directly to that lesson’s presentation. You may exit the slide show at any time by pressing the Esc key.

2 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Chapter Presentation Transparencies Bellringer Standardized Test PrepVisual Concepts Sample Problems Resources

3 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Table of Contents Chapter 19 Carbon and Organic Compounds Section 1 Compounds of Carbon Section 2 Names and Structures of Organic Compounds Section 3 Organic Reactions

4 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Bellringer Write a list of facts that you already know about carbon. Draw the Lewis diagram for carbon. Section 1 Compounds of Carbon Chapter 19

5 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Objectives Explain the unique properties of carbon that make the formation of organic molecules possible. Relate the structures of diamond, graphite, and other allotropes of carbon to their properties. Describe the nature of the bonds formed by carbon in alkanes, alkenes, alkynes, aromatic compounds, and cyclic compounds. Section 1 Compounds of Carbon Chapter 19

6 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Objectives, continued Classify organic compounds such as alcohols, esters, and ketones by their functional groups. Explain how the structural difference between isomers is related to the difference in their properties. Section 1 Compounds of Carbon Chapter 19

7 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Properties of Carbon Carbon atoms nearly always form covalent bonds. Three factors make carbon-carbon bonds unique: First, carbon-carbon bonds are quite strong Second, carbon compounds are not very reactive. Third, carbon can form up to four single covalent bonds, so a wide variety of compounds is possible. Section 1 Compounds of Carbon Chapter 19

8 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Properties of Carbon, continued Carbon Exists in Different Allotropes As an element, carbon atoms can form different bonding arrangements, or allotropes. The different allotropes have properties that differ due to the different arrangements of the carbon bonds. Section 1 Compounds of Carbon Chapter 19 Other Carbon Allotropes Include Fullerenes and Nanotubes Besides diamond and graphite, carbon allotropes include buckminsterfullerene, and nanotubes.

9 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Allotropes of Carbon Section 1 Compounds of Carbon Chapter 19

10 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Comparing Allotropes of Carbon Visual Concepts Chapter 19

11 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Organic Compounds Organic compounds contain carbon, and most also contain atoms of hydrogen. They can contain other elements, such as oxygen, nitrogen, sulfur, phosphorus, and the halogens. Chemists group organic compounds with similar characteristics into classes. The simplest class of organic compounds, hydrocarbons, contain only carbon and hydrogen. Section 1 Compounds of Carbon Chapter 19

12 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Organic Compound Visual Concepts Chapter 19

13 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Hydrocarbon Visual Concepts Chapter 19

14 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Organic Compounds, continued Alkanes Are the Simplest Hydrocarbons Alkanes are hydrocarbons with carbon atoms that are connected only by single bonds. Three alkanes are methane, ethane, and propane. The formulas of the alkanes fit the general formula C n H 2n+2, where n is the number of carbon atoms. For example, if an alkane has 30 carbon atoms, then its formula is C 30 H 62. Section 1 Compounds of Carbon Chapter 19

15 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Alkane Visual Concepts Chapter 19

16 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Organic Compounds, continued Many Hydrocarbons Have Multiple Bonds Alkenes are hydrocarbons that contain at least one double bond between two carbon atoms. Alkenes with one double bond have a general formula that is written C n H 2n. Alkynes are hydrocarbons that contain at least one triple bond between two carbon atoms. An alkyne with one triple bond is written as C n H 2n−2. Section 1 Compounds of Carbon Chapter 19

17 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Alkene Visual Concepts Chapter 19

18 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Alkyne Visual Concepts Chapter 19

19 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Organic Compounds, continued Carbon Atoms Can Form Rings Carbon atoms that form covalent bonds with one another can be arranged in a straight line or in a branched arrangement. Carbon bonds can also be arranged in a ring structure. The prefix cyclo- is added to the name of an alkane to indicate that it has a ring structure. Section 1 Compounds of Carbon Chapter 19

20 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Cycloalkane Visual Concepts Chapter 19

21 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Organic Compounds, continued Benzene Is an Important Ring Compound An important organic ring compound is the hydrocarbon benzene, C 6 H 6. Benzene is the simplest aromatic hydrocarbon. It can be drawn as a ring with three double bonds. Experiments show that all the carbon-carbon bonds in benzene are the same, so it is a molecule with resonance structures. Section 1 Compounds of Carbon Chapter 19

22 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Benzene Visual Concepts Chapter 19

23 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Other Organic Compounds Other classes of organic compounds contain other atoms such as oxygen, nitrogen, sulfur, phosphorus, and the halogens along with carbon and hydrogen. The word organic originally described only compounds made by living things. Now chemists can make organic compounds from inorganic substances. Section 1 Compounds of Carbon Chapter 19 Many Compounds Contain Functional Groups A typical organic compound has a group of atoms that is responsible for its chemical properties. This a group of atoms is known as a functional group.

24 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Other Organic Compounds, continued Many Compounds Contain Functional Groups, continued Organic compounds are commonly classified by the functional groups they contain. Because single bonds between carbon atoms rarely react, functional groups are often responsible for how an organic compound reacts. Section 1 Compounds of Carbon Chapter 19

25 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Functional Group Visual Concepts Chapter 19

26 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Other Organic Compounds, continued Comparing Classes of Organic Compounds Section 1 Compounds of Carbon Chapter 19

27 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Other Organic Compounds, continued Functional Groups Determine Properties The presence of a functional group causes an organic compound to have properties that differ greatly from those of the corresponding hydrocarbon. The structural formulas of butane and 1-butanol both have 4 carbon atoms joined by single bonds in a line. Butane is a gas at room temperature, but 1-butanol is a liquid and has a greater density and higher melting and boiling points than butane. The only difference between butane and 1-butanol is the presence of the functional group —OH on one of the carbon atoms in 1-butanol. Section 1 Compounds of Carbon Chapter 19

28 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Classes of Organic Compounds Visual Concepts Chapter 19

29 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Other Organic Compounds, continued Different Isomers Have Different Properties Both molecules below are alcohols and have the same molecular formula: C 4 H 10 O. Section 1 Compounds of Carbon Chapter 19

30 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Other Organic Compounds, continued Different Isomers Have Different Properties, continued The molecules of 1-butanol and 2-methyl-1-propanol differ in the way in which their atoms are arranged. Isomers are compounds that have the same formula but differ in their chemical and physical properties because of the difference in the arrangement of their atoms. The greater the structural difference between two isomers, the more they will differ in their properties. Section 1 Compounds of Carbon Chapter 19

31 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Section 2 Names and Structures of Organic Compounds Bellringer Examine the table on the next slide. Determine what organizing principles you see that will help you quickly process all the information contained in the table. Answer: Each formula beyond ethane contains one more —CH 2 — group. Beyond butane, the formulas are designated by their prefixes. Chapter 19

32 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Section 2 Names and Structures of Organic Compounds Bellringer, continued Chapter 19

33 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Objectives Name simple hydrocarbons from their structural formulas. Name branched hydrocarbons from their structural formulas. Identify functional groups from a structural formula, and assign names to compounds containing functional groups. Draw and interpret structural formulas and skeletal structures for common organic compounds. Section 2 Names and Structures of Organic Compounds Chapter 19

34 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming Straight-Chain Hydrocarbons Inorganic carbon compounds are named by using a system of prefixes and suffixes. Organic compounds have their own system of prefixes and suffixes that denote classes. For example, the names of all alkanes end with the suffix -ane. For alkanes that consist of five or more carbon atoms, the prefix comes from a Latin word that indicates the number of carbon atoms in the chain. Section 2 Names and Structures of Organic Compounds Chapter 19

35 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming Straight-Chain Hydrocarbons, continued Section 2 Names and Structures of Organic Compounds Chapter 19

36 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming Straight-Chain Hydrocarbons, continued Naming Short-Chain Alkenes and Alkynes Section 2 Names and Structures of Organic Compounds Chapter 19 A saturated hydrocarbon is one in which each carbon atom forms four single covalent bonds. The alkanes are saturated hydrocarbons. An unsaturated hydrocarbon is one in which not all carbon atoms have four single covalent bonds. Alkenes and alkynes are unsaturated hydrocarbons.

37 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Saturated Hydrocarbons Visual Concepts Chapter 19

38 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Unsaturated Hydrocarbons Visual Concepts Chapter 19

39 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming Straight-Chain Hydrocarbons, continued Naming Short-Chain Alkenes and Alkynes, continued Section 2 Names and Structures of Organic Compounds Chapter 19 The rules for naming an unsaturated hydrocarbon with fewer than four carbon atoms are similar to those for naming alkanes. A two-carbon alkene is named ethene, with the suffix -ene indicating that the molecule is an alkene. A three-carbon alkyne is named propyne, with the suffix –yne indicating that the molecule is an alkyne.

40 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming Straight-Chain Hydrocarbons, continued Naming Long-Chain Alkenes and Alkynes Section 2 Names and Structures of Organic Compounds Chapter 19 The name for an unsaturated hydrocarbon containing four or more carbon atoms must indicate the position of the double or triple bond within the molecule. First number the C atoms in the chain so that the first C atom in the double bond has the lowest number. If there is more than one multiple bond in a molecule, number the position of each multiple bond, and use a prefix to indicate the number of multiple bonds.

41 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming Straight-Chain Hydrocarbons, continued Naming Long-Chain Alkenes and Alkynes, continued Section 2 Names and Structures of Organic Compounds Chapter 19 The molecules on the left is correctly numbered from left to right because the first carbon atom with the double bond must have the lowest number.

42 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming Straight-Chain Hydrocarbons, continued Naming Long-Chain Alkenes and Alkynes, continued Section 2 Names and Structures of Organic Compounds For example, the following molecule is called 1,3-pentadiene. Chapter 19 (Note the placement of the prefix di-.)

43 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming Branched Hydrocarbons Section 2 Names and Structures of Organic Compounds Chapter 19 When a hydrocarbon is not a simple straight chain, first count the carbon atoms in the longest chain. The named is based on the corresponding alkane. The compound below has a “parent” chain that contains 7 carbon atoms, so it is heptane. Next, number the C atoms so that any branches on the chain have the lowest numbers possible.

44 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Using Prefixes to Name Organic Compounds Visual Concepts Chapter 19

45 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming Branched Hydrocarbons, continued Name the Attached Groups and Indicate Their Positions Section 2 Names and Structures of Organic Compounds Chapter 19 The third carbon atom has a —CH 3 group attached. This group is known as a methyl group. Because the methyl group is attached to the third C, the complete name is 3-methylheptane.

46 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming Branched Hydrocarbons, continued Name the Attached Groups and Indicate Their Positions, continued Section 2 Names and Structures of Organic Compounds Chapter 19 You can omit the numbers if there is no possibility of ambiguity. For example, a propane chain can have a methyl group only on its second carbon. If the methyl group were on the first or third carbon of propane, the molecule would be butane. So, 2-methylpropane is called methylpropane.

47 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming Branched Hydrocarbons, continued Name the Attached Groups and Indicate Their Positions, continued Section 2 Names and Structures of Organic Compounds Chapter 19 With unsaturated hydrocarbons that have attached groups, the longest chain containing the double bond is considered the parent compound. In addition, if more than one group is attached to the longest chain, the position of attachment of each group is given. Prefixes are used if the same group is attached more than once.

48 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming Branched Hydrocarbons, continued Name the Attached Groups and Indicate Their Positions, continued Section 2 Names and Structures of Organic Compounds Chapter 19 The chain with the double bond has 5 C atoms, so the compound is a pentene. The 1 st C atom has a double bond, so it is 1-pentene. Two methyl groups are attached to the third carbon atom, so the name is 3,3-dimethyl-1-pentene.

49 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming a Branched Hydrocarbon Sample Problem A Name the following hydrocarbon. Chapter 19 Section 2 Names and Structures of Organic Compounds

50 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming a Branched Hydrocarbon, continued Sample Problem A Solution The triple bond makes the branched hydrocarbon an alkyne. Identify the longest continuous chain and name it. Number the parent chain so that the triple bond is attached to the C atom with the lowest number. Name the groups that make up the branches. Chapter 19 Section 2 Names and Structures of Organic Compounds

51 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming a Branched Hydrocarbon, continued Sample Problem A Solution, continued Identify the positions that the branches occupy on the longest chain. The longest continuous chain has four carbon atoms. The parent chain is butyne. Section 2 Names and Structures of Organic Compounds Chapter 19

52 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu The numbering begins with the triple bond. Two methyl, —CH 3, groups are present. Both methyl groups are attached to the third carbon atom. The name is: 3, 3-dimethyl-1-butyne. Chapter 19 Section 2 Names and Structures of Organic Compounds Naming a Branched Hydrocarbon, continued Sample Problem A Solution, continued

53 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming Branched Hydrocarbons, continued Names of Compounds Reflect Functional Groups Section 2 Names and Structures of Organic Compounds Chapter 19 Names for organic compounds with functional groups are based on the same system for branched chains. First, the longest chain is named. Then a prefix or suffix indicating the functional group is added to the hydrocarbon name. When necessary, the position of the functional group is noted just as with hydrocarbon branches.

54 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming Branched Hydrocarbons, continued Naming Compounds with Functional Groups Section 2 Names and Structures of Organic Compounds Chapter 19 A prefix or suffix can indicate a functional group.

55 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming Branched Hydrocarbons, continued Names of Compounds Reflect Functional Groups, continued Section 2 Names and Structures of Organic Compounds Chapter 19 Because the longest chain in the structure below has three C atoms, the name is based on propane. The —OH functional group classifies it as an alcohol. Because the —OH is attached to the second C atom, the correct name for this compound is 2-propanol.

56 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming a Compound with a Functional Group Sample Problem B Name the following organic compound. Chapter 19 Section 2 Names and Structures of Organic Compounds

57 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Naming a Compound with a Functional Group, continued Sample Problem B Solution The functional group indicates that this compound is a ketone. Identify the longest continuous chain and name it. Number the parent chain so that the functional group is attached to the C atom with the lowest number. Identify the position the functional group occupies on the longest chain, and name the organic compound. Chapter 19 Section 2 Names and Structures of Organic Compounds

58 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Sample Problem B Solution, continued The longest continuous chain has six carbon atoms: the parent chain is hexane. The carbon atoms are numbered from right to left to give the ketone functional group the lowest number. Naming a Compound with a Functional Group, continued Section 2 Names and Structures of Organic Compounds Chapter 19 The name of this organic compound is 3-hexanone.

59 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Representing Organic Molecules Section 2 Names and Structures of Organic Compounds Chapter 19 There are many ways of depicting organic molecules. Each type of model used to represent an organic compound has both advantages and disadvantages. They can highlight different features such as the number and kinds of atoms or the three-dimensional shape of the space-filling model. A model cannot fully show the true three-dimensional shape of a molecule or show the motion within a molecule caused by the atoms’ constant vibration.

60 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Types of Molecular Models Section 2 Names and Structures of Organic Compounds Chapter 19

61 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Structural Formula Visual Concepts Chapter 19

62 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Representing Organic Molecules, continued Structural Formulas Can Be Simplified Section 2 Names and Structures of Organic Compounds Chapter 19 Structural formulas are sometimes represented by skeletal structures, which show bonds, but leave out some or even all of the carbon and hydrogen atoms. Skeletal structures usually show the carbon framework only as lines representing bonds. These lines form a zigzag pattern to indicate the tetrahedral arrangement of bonds. Atoms other than C and H are always shown.

63 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Representing Organic Molecules, continued Structural Formulas Can Be Simplified, continued Section 2 Names and Structures of Organic Compounds Chapter 19 In structural formulas, C and H atoms are not shown unless they are part of functional groups.

64 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Drawing Structural and Skeletal Formulas Sample Problem C Draw both the structural formula and the skeletal structure for 1,2,3-propanetriol. Chapter 19 Section 2 Names and Structures of Organic Compounds

65 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Drawing Structural and Skeletal Formulas, continued Sample Problem C Solution The name propanetriol indicates that the molecule is an alcohol that has three C atoms in the parent chain. The suffix -triol means that there are 2 alcohol groups. The 1,2,3- prefix indicates that an alcohol group is attached to the first, second, and third carbon atoms. Draw the carbon framework, and add the alcohol groups to the appropriate carbon atoms. Chapter 19 Section 2 Names and Structures of Organic Compounds

66 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Drawing Structural and Skeletal Formulas, continued Sample Problem C Solution, continued Add H atoms so that each C atom has 4 bonds. Show the carbon framework as a zigzag line. Include the functional groups as part of the structure. Chapter 19 Section 2 Names and Structures of Organic Compounds

67 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Section 3 Organic Reactions Bellringer Read the definitions of the key terms in this section and find a reaction that would illustrate each term. Keep your definitions and check for correctness as you study this section. Chapter 19

68 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Objectives Describe and distinguish between substitution and addition reactions. Describe and distinguish between condensation and elimination reactions. Section 3 Organic Reactions Chapter 19

69 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Substitution and Addition Reactions Organic compounds participate in a variety of chemical reactions. A substitution reaction is a reaction in which one or more atoms replace another atom or group of atoms in a molecule. An addition reaction is a reaction in which an atom or molecule is added to an unsaturated molecule and increases the saturation of the molecule. Section 3 Organic Reactions Chapter 19

70 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Substitution and Addition Reactions, continued Halogens Often Replace Hydrogen Atoms One substitution reaction occurs when a halogen, such as a chlorine atom, replaces a hydrogen atom on an alkane molecule, such as methane. The substitution reactions can continue, replacing the remaining H atoms in methane one at a time. The products are dichloromethane, trichloromethane, and tetrachloromethane (commonly known as chloroform). Section 3 Organic Reactions Chapter 19

71 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Substitution Reaction Visual Concepts Chapter 19

72 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Substitution and Addition Reactions, continued Hydrogenation Is a Common Addition Reaction One addition reaction is hydrogenation, in which H atoms are added to an unsaturated molecule. The product of the reaction contains fewer double or triple bonds than the reactant. Section 3 Organic Reactions Chapter 19

73 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Addition Reaction Visual Concepts Chapter 19

74 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Substitution and Addition Reactions, continued Making Consumer Products by Hydrogenation Another kind of hydrogenation is the manufacture of cyclohexane from benzene as shown below. Section 3 Organic Reactions Chapter 19 Over 90% of the cyclohexane that is made is used in the manufacture of nylon.

75 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Substitution and Addition Reactions, continued Some Addition Reactions Form Polymers Some addition reactions involve joining smaller molecules together to make larger ones. The smaller molecules are known as monomers. The larger molecule that is made by the addition reaction is called a polymer. Polyethylene is a strong but flexible plastic that is made from ethane monomers, C 2 H 4. Section 3 Organic Reactions Chapter 19

76 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Substitution and Addition Reactions, continued Some Addition Reactions Form Polymers, continued Because ethene is commonly known as ethylene, the polymer it forms is often called polyethylene. The following equation shows how a portion of the polymer forms. Section 3 Organic Reactions Chapter 19

77 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Substitution and Addition Reactions, continued Monomers Can Be Added in Different Ways Polyethylene is a very long alkane polymer chain. The chains form a product that is strong yet flexible. Monomers can be added so that a chain branches. For example, an ethene monomer is sometimes added to form a side chain. A polymer with many side chains remain flexible. Section 3 Organic Reactions Chapter 19

78 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Condensation and Elimination Polymers can also be formed by a condensation reaction in which two molecules combine, usually accompanied by the loss of a water molecule. The formation of water as a reaction product is the reason for the name of this type of reaction. An elimination reaction is a reaction in which a simple molecule is removed from adjacent carbon atoms on the same organic molecule. An elimination reaction also produces water. Section 3 Organic Reactions Chapter 19

79 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Condensation and Elimination, continued Condensation Reactions Produce Nylon Nylon is formed in a condensation reaction. The reaction takes place between an amine group on hexanediamine and a carboxyl group on adipic acid. A water molecule is eliminated when an H atom from the amine group and an —OH group from the carboxyl group are removed. This reaction repeats, linking hundreds of reactants to form the synthetic polymer called nylon 66. Section 3 Organic Reactions Chapter 19

80 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Condensation Polymers Visual Concepts Chapter 19

81 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Condensation and Elimination, continued Many Polymers Form by Condensation Reactions The polymer polyethylene terephthalate, abbreviated PET, is formed when two monomers are combined in the following condensation reaction. Section 3 Organic Reactions Chapter 19 The functional group present in the product shown above classifies this molecule as an ester, so PET is a polyester.

82 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Condensation and Elimination, continued Elimination Reactions Often Form Water An elimination reaction involves the removal of a small molecule from two adjacent carbon atoms. Section 3 Organic Reactions Chapter 19 The acid catalyzes a reaction that eliminates water from ethanol, which leaves a double bond.

83 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Elimination Reaction Visual Concepts Chapter 19

84 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 1.Which of these formulas represents a saturated hydrocarbon? A.C 2 H 2 B.C 4 H 10 C.C 5 H 10 D.C 6 H 6 Standardized Test Preparation Understanding Concepts Chapter 19

85 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 1.Which of these formulas represents a saturated hydrocarbon? A.C 2 H 2 B.C 4 H 10 C.C 5 H 10 D.C 6 H 6 Standardized Test Preparation Understanding Concepts Chapter 19

86 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 2.Which of these is the product of the hydrogenation of benzene? F.benzyl hydride G.cyclohexane H.hexane I.1-hexanol Standardized Test Preparation Understanding Concepts Chapter 19

87 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 2.Which of these is the product of the hydrogenation of benzene? F.benzyl hydride G.cyclohexane H.hexane I.1-hexanol Standardized Test Preparation Understanding Concepts Chapter 19

88 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 3.Which of the following occurs during an addition reaction? A.The saturation of a molecule is increased. B.Single bonds are replaced by double bonds. C.A number of monomers react to form a polymer. D.One or more atoms replace another atom or group of atoms. Standardized Test Preparation Understanding Concepts Chapter 19

89 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 3.Which of the following occurs during an addition reaction? A.The saturation of a molecule is increased. B.Single bonds are replaced by double bonds. C.A number of monomers react to form a polymer. D.One or more atoms replace another atom or group of atoms. Standardized Test Preparation Understanding Concepts Chapter 19

90 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 4.Why is ethyne, also known as acetylene, used in welding torches instead of ethane which also has two carbon atoms? Standardized Test Preparation Understanding Concepts Chapter 19

91 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 4.Why is ethyne, also known as acetylene, used in welding torches instead of ethane which also has two carbon atoms? Answer: Welding requires very high temperatures. The triple bond of acetylene releases much more energy than the single bond of ethane, creating a higher temperature flame. Standardized Test Preparation Understanding Concepts Chapter 19

92 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 5.Why does a hydrogenation reaction never include an alkane as a reactant? Standardized Test Preparation Understanding Concepts Chapter 19

93 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 5.Why does a hydrogenation reaction never include an alkane as a reactant? Answer: Because hydrogenation always includes a multiple bond. Standardized Test Preparation Understanding Concepts Chapter 19

94 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 6.Sunflower oil contains polyunsaturated fat molecules. What does polyunsaturated mean? Standardized Test Preparation Understanding Concepts Chapter 19

95 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 6.Sunflower oil contains polyunsaturated fat molecules. What does polyunsaturated mean? Answer: It has more than one double or triple carbon- carbon bond. Standardized Test Preparation Understanding Concepts Chapter 19

96 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Read the passage below. Then answer the questions. In the early part of the nineteenth century, chemists were unable to synthesize most carbon- containing compounds, unless they started with a material that had been produced by a living organism. The predominant theory was that there was a force inherent in living organisms that had to be used to make these compounds. In 1828 a German chemist, Friedrich Wöhler, succeeded in making an organic compound, urea, starting with inorganic chemicals. Although many chemists did not immediately accept that there was no living force involved in making organic molecules, the results prompted other scientists to perform experiments that led to synthesis of a variety of carbon compounds from inorganic sources and eventually new chemical theories. Standardized Test Preparation Reading Skills Chapter 19

97 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 7.Why did Wöhler's synthesis of urea from inorganic compounds mean that the theory about organic materials had to be reevaluated? F.It showed that other chemists were wrong. G.It proved that urea is not an organic compound. H.New data was not consistent with the existing theory. I.There is no special force existant that organisms use to make compounds. Standardized Test Preparation Reading Skills Chapter 19

98 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 7.Why did Wöhler's synthesis of urea from inorganic compounds mean that the theory about organic materials had to be reevaluated? F.It showed that other chemists were wrong. G.It proved that urea is not an organic compound. H.New data was not consistent with the existing theory. I.There is no special force existant that organisms use to make compounds. Standardized Test Preparation Reading Skills Chapter 19

99 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 8.Why wasn't the theory that living organisms contributed special characteristics to organic compounds immediately replaced in the scientific community as soon as Wöhler announced his results? Standardized Test Preparation Reading Skills Chapter 19

100 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 8.Why wasn't the theory that living organisms contributed special characteristics to organic compounds immediately replaced in the scientific community as soon as Wöhler announced his results? Answer: A single experiment from one laboratory is not always enough to convince everyone that the new data is valid and that the accepted theory is now disproven. Standardized Test Preparation Reading Skills Chapter 19

101 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Use the table below to answer questions 9 through 12. Comparing Classes of Organic Compounds Standardized Test Preparation Interpreting Graphics Chapter 19

102 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 9.Which of the following statements is supported by the data in the table? A.The density of an organic molecule is primarily a function of the number of carbons it contains. B.A double bond between carbon and oxygen increases the boiling point more than a single bond. C.The increase in melting and boiling points of organic compounds is related to the polarity of functional groups. D.The increase in melting and boiling points of oxygen- containing organic molecules compared to hydrocarbons is primarily due to the polarity of the oxygen-hydrogen bond. Standardized Test Preparation Interpreting Graphics Chapter 19

103 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 9.Which of the following statements is supported by the data in the table? A.The density of an organic molecule is primarily a function of the number of carbons it contains. B.A double bond between carbon and oxygen increases the boiling point more than a single bond. C.The increase in melting and boiling points of organic compounds is related to the polarity of functional groups. D.The increase in melting and boiling points of oxygen- containing organic molecules compared to hydrocarbons is primarily due to the polarity of the oxygen-hydrogen bond. Standardized Test Preparation Interpreting Graphics Chapter 19

104 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 10.What is the main reason that the melting point of 2-butanone differs from that of butane? F.the loss of a hydrogen atom G.the increase in molecular size H.the increase in intermolecular forces I.the presence of oxygen in the molecule Standardized Test Preparation Interpreting Graphics Chapter 19

105 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 10.What is the main reason that the melting point of 2-butanone differs from that of butane? F.the loss of a hydrogen atom G.the increase in molecular size H.the increase in intermolecular forces I.the presence of oxygen in the molecule Standardized Test Preparation Interpreting Graphics Chapter 19

106 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 11.Identify two pairs of isomeric compounds in the table. Standardized Test Preparation Interpreting Graphics Chapter 19

107 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 11.Identify two pairs of isomeric compounds in the table. Answer: 1-butanol and diethyl ether; butanoic acid/2-butanone Standardized Test Preparation Interpreting Graphics Chapter 19

108 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu Standardized Test Preparation Interpreting Graphics Chapter In °C, by how much does the introduction of a hydroxyl group on the end carbon of the butane molecule increase the melting point?

109 Copyright © by Holt, Rinehart and Winston. All rights reserved. ResourcesChapter menu 12.In °C, by how much does the introduction of a hydroxyl group on the end carbon of the butane molecule increase the melting point? Answer: 48.9 Standardized Test Preparation Interpreting Graphics Chapter 19


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