1. Lecture Notes Alan D. Earhart Southeast Community College Lincoln, NE Chapter 23 Organic Chemistry John E. McMurry Robert C. Fay CHEMISTRY Fifth Edition Copyright © 2008 Pearson Prentice Hall, Inc.

2. Chapter 23/2 The Nature of Organic Molecules Carbon is tetravalent. It has four outer-shell electrons (1s 2 2s 2 2p 2 ) and forms four bonds. Organic Chemistry: The study of carbon compounds.

3. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/3 The Nature of Organic Molecules Organic molecules have covalent bonds. In ethane, for instance, all bonds result from the sharing of two electrons.

4. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/4 The Nature of Organic Molecules Organic molecules have polar covalent bonds when carbon bonds to an element on the right or left side of the periodic table.

5. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/5 The Nature of Organic Molecules Carbon can form multiple covalent bonds by sharing more than two electrons with a neighboring atom.

6. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/6 The Nature of Organic Molecules Organic molecules have specific three-dimensional shapes, which can be predicted by the VSEPR model.

7. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/7 The Nature of Organic Molecules Organic molecules have specific three-dimensional shapes, which can be predicted by the VSEPR model.

8. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/8 The Nature of Organic Molecules Carbon uses hybrid atomic orbitals for bonding.

9. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/9 Alkanes and Their Isomers Hydrocarbons: Molecules that contain only carbon and hydrogen. Alkanes: Hydrocarbons that contain only single bonds. Space-filling models: Structural formulas: Molecular formulas:

11. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/11 Alkanes and Their Isomers Isomers: Compounds with the same molecular formula but different chemical structures.

12. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/12 Drawing Organic Structures Condensed Formula Structural Formula

13. The Shapes of Organic Molecules

14. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/14 Naming Alkanes IUPAC Rules Alkane

15. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/15 Naming Alkanes 1.Name the main chain. Find the longest continuous chain of carbons in the molecule, and use the name of that chain as the parent name:

16. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/16 Naming Alkanes 2.Number the carbon atoms in the main chain. Beginning at the end nearer the first branch point, number each carbon atom in the parent chain:

17. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/17 Naming Alkanes 3.Identify and number the branching substituent. Assign a number to each branching substituent group on the parent chain according to its point of attachment:

18. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/18 Naming Alkanes 3.Identify and number the branching substituent. Assign a number to each branching substituent group on the parent chain according to its point of attachment:

19. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/19 Naming Alkanes Write the name as a single word. Use hyphens to separate the different prefixes, and use commas to separate numbers when there are more than one. If two or more different substituent groups are present, list them in alphabetical order. If two or more identical substituent groups are present, use one of the Greek prefixes:

20. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/20 Naming Alkanes

22. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/22 Cycloalkanes Cycloalkane: One or more rings of carbon atoms. 6 C3 C4 C5 C

23. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/23 Cycloalkanes

24. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/24 Cycloalkanes

25. Reactions of Alkanes Halogens (Cl 2 or Br 2 ): CO 2 (g) + 2H 2 O(l)CH 4 (g) + 2O 2 (g)  H° = -890 kJ Combustion:

26. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/26 Families of Organic Molecules: Functional Groups Functional Group: An atom or group of atoms within a molecule that has a characteristic chemical behavior and that undergoes the same kinds of reactions in every molecule where it occurs.

27. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/27

30. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/30 Alkenes and Alkynes Alkene: A hydrocarbon that contains a carbon-carbon double bond. Alkyne: A hydrocarbon that contains a carbon-carbon triple bond. Unsaturated: A hydrocarbon that contains fewer hydrogens per carbon than the related alkane.

31. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/31 Alkenes and Alkynes Alkenes -ene suffix since they are alkenes.

32. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/32 Alkenes and Alkynes Alkenes and Isomers

33. Alkenes and Alkynes Alkenes and Isomers

34. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/34 Alkenes and Alkynes Alkenes and Isomers Why are they isomers?

35. Alkenes and Alkynes Alkenes and Isomers

36. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/36 Alkenes and Alkynes Alkynes -yne suffix since they are alkynes.

37. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/37 Reactions of Alkenes Addition of Hydrogen:

38. Reactions of Alkenes Addition of Hydrogen:

39. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/39 Reactions of Alkenes Addition of Cl 2 and Br 2 :

40. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/40 Reactions of Alkenes Addition of Water:

41. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/41 Aromatic Compounds and Their Reactions Aromatic: A class of compounds that contain a six- membered ring with three double bonds.

42. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/42 Aromatic Compounds and Their Reactions The stability of benzene comes from its six pi-bond electrons which are spread equally around the entire ring:

43. Aromatic Compounds and Their Reactions Nitration (Substitution of a Nitro Group):

44. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/44 Aromatic Compounds and Their Reactions Halogenation (Substitution of a Bromine or Chlorine):

45. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/45 Alcohols, Ethers, and Amines Alcohols: A class of compounds that contain a hydroxyl group (-OH).

46. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/46 Alcohols, Ethers, and Amines Simple alcohols are often soluble in water because of hydrogen bonding: Alcohols

47. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/47 Alcohols, Ethers, and Amines Alcohols -ol suffix since they are alcohols.

48. Alcohols, Ethers, and Amines Alcohols Some important alcohols:

49. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/49 Alcohols, Ethers, and Amines Alcohols Some important alcohols:

50. Alcohols, Ethers, and Amines Alcohols Some important alcohols:

51. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/51 Alcohols, Ethers, and Amines Ethers

52. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/52 Alcohols, Ethers, and Amines Amines

53. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/53 Alcohols, Ethers, and Amines Amines AcidBase

54. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/54 Aldehydes and Ketones All have carbonyl groups

55. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/55 Aldehydes and Ketones -one suffix since they are ketones. -al suffix since they are aldehydes.

56. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/56 Aldehydes and Ketones

57. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/57 Aldehydes and Ketones

58. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/58 Carboxylic Acids, Esters, and Amides These are bonded to a strongly electronegative atom (O or N).

59. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/59 Carboxylic Acids, Esters, and Amides All three undergo carbonyl-substitution reactions:

60. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/60 Carboxylic Acids, Esters, and Amides Carboxylic Acids

61. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/61 Carboxylic Acids, Esters, and Amides Carboxylic Acids They are weaker than their strong inorganic counterparts. For acetic acid, K a = 1.75 x 10 -5

62. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/62 Carboxylic Acids, Esters, and Amides Carboxylic Acids A common industrial solvent.

63. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/63 Carboxylic Acids, Esters, and Amides Esters Gives bananas their odor.

64. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/64 Carboxylic Acids, Esters, and Amides Esters Hydrolysis: Saponification (“soap”) is the base catalyzed hydrolysis of naturally occurring esters in animal fat.

65. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/65 Carboxylic Acids, Esters, and Amides Amides

66. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/66 Carboxylic Acids, Esters, and Amides Amides Hydrolysis:

67. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/67 Synthetic Polymers Polymers: Large molecules formed by the repetitive bonding of many smaller molecules, called monomers.

68. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/68 Synthetic Polymers

69. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/69 Synthetic Polymers Polymerization: Initiator

70. Copyright © 2008 Pearson Prentice Hall, Inc.Chapter 23/70 Synthetic Polymers Polymerization: