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2. Resources Chapter Presentation Bellringer Transparencies Sample Problems Visual Concepts Standardized Test Prep

3. Carbon and Organic Compounds Chapter 19 Table of Contents Section 1Compounds of Carbon Section 2Names and Structures of Organic Compounds Section 3Organic Reactions

4. Section1 Compounds of Carbon Chapter 19 Bellringer • Write a list of facts that you already know about carbon. • Draw the Lewis diagram for carbon.

5. Section1 Compounds of Carbon Chapter 19 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.

6. Section1 Compounds of Carbon Chapter 19 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.

7. Section1 Compounds of Carbon Chapter 19 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.

8. Section1 Compounds of Carbon Chapter 19 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. Other Carbon Allotropes Include Fullerenes and Nanotubes • Besides diamond and graphite, carbon allotropes include buckminsterfullerene, and nanotubes.

9. Allotropes of Carbon Section1 Compounds of Carbon Chapter 19

10. Visual Concepts Chapter 19 Comparing Allotropes of Carbon

11. Section1 Compounds of Carbon Chapter 19 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.

12. Visual Concepts Chapter 19 Organic Compound

13. Visual Concepts Chapter 19 Hydrocarbon

14. Section1 Compounds of Carbon Chapter 19 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 CnH2n+2, where n is the number of carbon atoms. • For example, if an alkane has 30 carbon atoms, then its formula is C30H62.

15. Visual Concepts Chapter 19 Alkane

16. Section1 Compounds of Carbon Chapter 19 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 CnH2n. • Alkynes are hydrocarbons that contain at least one triple bond between two carbon atoms. • An alkyne with one triple bond is written as CnH2n−2.

17. Visual Concepts Chapter 19 Alkene

18. Visual Concepts Chapter 19 Alkyne

19. Section1 Compounds of Carbon Chapter 19 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.

20. Visual Concepts Chapter 19 Cycloalkane

21. Section1 Compounds of Carbon Chapter 19 Organic Compounds, continued Benzene Is an Important Ring Compound • An important organic ring compound is the hydrocarbon benzene, C6H6. • 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.

22. Visual Concepts Chapter 19 Benzene

23. Section1 Compounds of Carbon Chapter 19 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. 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. Section1 Compounds of Carbon Chapter 19 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.

25. Visual Concepts Chapter 19 Functional Group

26. Section1 Compounds of Carbon Chapter 19 Other Organic Compounds, continued Comparing Classes of Organic Compounds

27. Section1 Compounds of Carbon Chapter 19 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-butanolis the presence of the functional group —OH on one of the carbon atoms in 1-butanol.

28. Visual Concepts Chapter 19 Classes of Organic Compounds

29. Section1 Compounds of Carbon Chapter 19 Other Organic Compounds, continued Different Isomers Have Different Properties • Both molecules below are alcohols and have the same molecular formula: C4H10O.

30. Section1 Compounds of Carbon Chapter 19 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.

31. Section2 Names and Structures of Organic Compounds Chapter 19 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 —CH2— group. Beyond butane, the formulas are designated by their prefixes.

32. Section2 Names and Structures of Organic Compounds Chapter 19 Bellringer, continued

33. Section2 Names and Structures of Organic Compounds Chapter 19 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.

34. Section2 Names and Structures of Organic Compounds Chapter 19 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.

35. Section2 Names and Structures of Organic Compounds Chapter 19 Naming Straight-Chain Hydrocarbons, continued

36. Section2 Names and Structures of Organic Compounds Chapter 19 Naming Straight-Chain Hydrocarbons, continued Naming Short-Chain Alkenes and Alkynes • A saturated hydrocarbon is one in which each carbon atom forms four single covalent bonds. • The alkanes are saturated hydrocarbons. • An unsaturated hydrocarbonis one in which not all carbon atoms have four single covalent bonds. • Alkenes and alkynes are unsaturated hydrocarbons.

37. Visual Concepts Chapter 19 Saturated Hydrocarbons

38. Visual Concepts Chapter 19 Unsaturated Hydrocarbons

39. Section2 Names and Structures of Organic Compounds Chapter 19 Naming Straight-Chain Hydrocarbons, continued Naming Short-Chain Alkenes and Alkynes, continued • 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. Section2 Names and Structures of Organic Compounds Chapter 19 Naming Straight-Chain Hydrocarbons, continued Naming Long-Chain Alkenes and Alkynes • 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. Section2 Names and Structures of Organic Compounds Chapter 19 Naming Straight-Chain Hydrocarbons, continued Naming Long-Chain Alkenes and Alkynes, continued • 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. Section2 Names and Structures of Organic Compounds Chapter 19 Naming Straight-Chain Hydrocarbons, continued Naming Long-Chain Alkenes and Alkynes, continued • For example, the following molecule is called1,3-pentadiene. • (Note the placement of the prefix di-.)

43. Section2 Names and Structures of Organic Compounds Chapter 19 Naming Branched Hydrocarbons • 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. Visual Concepts Chapter 19 Using Prefixes to Name Organic Compounds

45. Section2 Names and Structures of Organic Compounds Chapter 19 Naming Branched Hydrocarbons, continued Name the Attached Groups and Indicate Their Positions • The third carbon atom has a —CH3 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. Section2 Names and Structures of Organic Compounds Chapter 19 Naming Branched Hydrocarbons, continued Name the Attached Groups and Indicate Their Positions, continued • 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. Section2 Names and Structures of Organic Compounds Chapter 19 Naming Branched Hydrocarbons, continued Name the Attached Groups and Indicate Their Positions, continued • 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. Section2 Names and Structures of Organic Compounds Chapter 19 Naming Branched Hydrocarbons, continued Name the Attached Groups and Indicate Their Positions, continued • The chain with the double bond has 5 C atoms, so the compound is a pentene. • The 1st 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. Section2 Names and Structures of Organic Compounds Chapter 19 Naming a Branched Hydrocarbon Sample Problem A Name the following hydrocarbon.

50. Section2 Names and Structures of Organic Compounds Chapter 19 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.