1. John C. Kotz State University of New York, College at Oneonta John C. Kotz Paul M. Treichel John Townsend http://academic.cengage.com/kotz Chapter 10 Carbon: More Than Just Another Element

2. 2 © 2009 Brooks/Cole - Cengage Important – Read Before Using Slides in Class Instructor: This PowerPoint presentation contains photos and figures from the text, as well as selected animations and videos. For animations and videos to run properly, we recommend that you run this PowerPoint presentation from the PowerLecture disc inserted in your computer. Also, for the mathematical symbols to display properly, you must install the supplied font called “Symb_chm,” supplied as a cross-platform TrueType font in the “Font_for_Lectures” folder in the "Media" folder on this disc. If you prefer to customize the presentation or run it without the PowerLecture disc inserted, the animations and videos will only run properly if you also copy the associated animation and video files for each chapter onto your computer. Follow these steps: 1.Go to the disc drive directory containing the PowerLecture disc, and then to the “Media” folder, and then to the “PowerPoint_Lectures” folder. 2.In the “PowerPoint_Lectures” folder, copy the entire chapter folder to your computer. Chapter folders are named “chapter1”, “chapter2”, etc. Each chapter folder contains the PowerPoint Lecture file as well as the animation and video files. For assistance with installing the fonts or copying the animations and video files, please visit our Technical Support at http://academic.cengage.com/support or call (800) 423-0563. Thank you. http://academic.cengage.com/support

3. 3 © 2009 Brooks/Cole - Cengage ORGANIC CHEMISTRY

4. 4 © 2009 Brooks/Cole - Cengage cinnamaldehyde eugenol

5. 5 © 2009 Brooks/Cole - Cengage Types of Organic Compounds organic compounds.Vast majority of over 20 million known compounds are based on C: organic compounds. Generally contain C and H + other elements Great variety of compounds

6. 6 © 2009 Brooks/Cole - Cengage Isomerism Isomers have identical composition but different structuresIsomers have identical composition but different structures Two forms of isomerismTwo forms of isomerism –Constitutional (or structural) –Stereoisomerism ConstitutionalConstitutional –Same empirical formula but different atom- to-atom connections StereoisomerismStereoisomerism –Same atom-to-atom connections but different arrangement in space.

7. 7 © 2009 Brooks/Cole - Cengage Structural Isomers

8. 8 © 2009 Brooks/Cole - Cengage Cis-2-butene Stereoisomers: Geometric Geometric isomers can occur when there is a C=C double bond. Trans-2-butene

9. 9 © 2009 Brooks/Cole - Cengage Optical isomers are molecules with non-superimposable mirror images.Optical isomers are molecules with non-superimposable mirror images. Such molecules are called CHIRALSuch molecules are called CHIRAL Pairs of chiral molecules are enantiomers.Pairs of chiral molecules are enantiomers. Chiral molecules in solution can rotate the plane of plane polarized light.Chiral molecules in solution can rotate the plane of plane polarized light. Stereoisomers: Optical

10. 10 © 2009 Brooks/Cole - Cengage Chiral Compounds—Polarized Light

11. 11 © 2009 Brooks/Cole - Cengage Stereoisomers Isomers Chirality generally occurs when a C atom has 4 different groups attached. Lactic acid

12. 12 © 2009 Brooks/Cole - Cengage Stereoisomers Isomers Lactic acid isomers are nonsuperimposable

13. 13 © 2009 Brooks/Cole - Cengage Chirality: Handedness in Nature These molecules are non-superimposable mirror images.

14. 14 © 2009 Brooks/Cole - Cengage Chirality: Handedness in Nature These amino acids are non- superimposable mirror images.

15. 15 © 2009 Brooks/Cole - Cengage Stereoisomers in Nature Right- and left- handed seashells The DNA here is right-handed

16. 16 © 2009 Brooks/Cole - Cengage The egg cases of the whelk have a right- handed twist.

17. 17 © 2009 Brooks/Cole - Cengage Compounds of C and HCompounds of C and H Subgroups:Subgroups: –Alkanes: C-C single bonds –Alkenes: C=C double bonds –Alkynes: carbon-carbon triple bonds –Aromatic: based on benzene Hydrocarbons

18. 18 © 2009 Brooks/Cole - Cengage Alkanes have the general formula C n H 2n+2Alkanes have the general formula C n H 2n+2 CH 4 = methaneCH 4 = methane C 2 H 6 = ethaneC 2 H 6 = ethane C 3 H 8 = propaneC 3 H 8 = propane C 4 H 10 = butaneC 4 H 10 = butane C 5 H 12 = pentaneC 5 H 12 = pentane Hydrocarbons

19. 19 © 2009 Brooks/Cole - Cengage

20. 20 Methane Hydrate, CH 4 (H 2 O) x

21. 21 © 2009 Brooks/Cole - Cengage Hydrocarbons & Structural Isomerism C 5 H 12 has 3 structural isomers. C 6 H 14 has 5 C 7 H 14 has 9 C 5 H 12 has 3 structural isomers. C 6 H 14 has 5 C 7 H 14 has 9 Isomers of C 5 H 12 ? Note names of isomers

22. 22 © 2009 Brooks/Cole - Cengage Alkanes are colorless gases, liquids, and solids Generally unreactive (but undergo combustion) Not polar (or low polarity) and so are not soluble in water. Hydrocarbons: Alkanes

23. 23 © 2009 Brooks/Cole - Cengage All compounds are flexible. Cyclohexane, C 6 H 12, has interconverting “chair” and “boat” forms. Hydrocarbons: Cycloalkanes

24. 24 © 2009 Brooks/Cole - Cengage Alkenes: Compounds with C=C Double Bonds How many isomers are possible for a compound with the formula C 4 H 8 ?How many isomers are possible for a compound with the formula C 4 H 8 ?

25. 25 © 2009 Brooks/Cole - Cengage Alkenes— Many Occur Naturally

26. 26 © 2009 Brooks/Cole - Cengage Reactions of Alkenes: ADDITION REACTIONS Alkenes are unsaturated — more bonds can form to the C atomsAlkenes are unsaturated — more bonds can form to the C atoms Molecules such as Br 2, H 2, HCl, HBr, and H 2 O add to the double bondMolecules such as Br 2, H 2, HCl, HBr, and H 2 O add to the double bond

27. 27 © 2009 Brooks/Cole - Cengage An Addition Reaction The fat in bacon is partially unsaturated. The fat adds Br 2 to the C=C bonds.The fat in bacon is partially unsaturated. The fat adds Br 2 to the C=C bonds. Fats can be “hydrogenated” with H 2.Fats can be “hydrogenated” with H 2. Fat placed in Br 2 vapor

28. 28 © 2009 Brooks/Cole - Cengage An Addition Reaction Fat placed in Br 2 vapor PLAY MOVIE

29. 29 © 2009 Brooks/Cole - Cengage An Addition Reaction Fats can be “hydrogenated” with H 2.Fats can be “hydrogenated” with H 2. Peanut butter has partially hydrogenated vegetable oil. PLAY MOVIE

30. 30 © 2009 Brooks/Cole - Cengage Trans Fatty Acids tend to raise total blood cholesterol CH 3 (CH 2 ) 7 CH=CH(CH 2 ) 7 CO 2 H

31. 31 © 2009 Brooks/Cole - Cengage Trans Fatty Acids Food Percentages of Trans- Fatty Acids Butter 3.6 Soft Margarine 5.2 Hard Margarine 12.4 Vegetable Oils, Including Safflower, Sunflower, and Soy 0 Beef burger, Fried or Grilled 0.8 Chocolate Cake with Icing 7.1

32. 32 © 2009 Brooks/Cole - Cengage Alkynes Alkynes have carbon-carbon triple bonds.Alkynes have carbon-carbon triple bonds. C 2 H 2 : common name = acetylene systematic name = ethyneC 2 H 2 : common name = acetylene systematic name = ethyne Preparation: CaC 2 (s) + H 2 O(liq) --> C 2 H 2 (g) + Ca(OH) 2 (s) ∆ f H o (C 2 H 2, g) = +226.7 kJ/mol Preparation: CaC 2 (s) + H 2 O(liq) --> C 2 H 2 (g) + Ca(OH) 2 (s) ∆ f H o (C 2 H 2, g) = +226.7 kJ/mol ∆ r H for C 2 H 2 + O 2 = –1300 kJ/mol

33. 33 © 2009 Brooks/Cole - Cengage Aromatic Compounds Benzene, C 6 H 6, in the top 25 chemicals produced in the U.S.Benzene, C 6 H 6, in the top 25 chemicals produced in the U.S. Starting point for hundreds of other compounds.Starting point for hundreds of other compounds.

34. 34 © 2009 Brooks/Cole - Cengage Resonance in Benzene C 6 H 6 has two resonance structures with alternating double bonds.C 6 H 6 has two resonance structures with alternating double bonds. The π electrons are delocalized over the ring.The π electrons are delocalized over the ring.

35. 35 © 2009 Brooks/Cole - Cengage Resonance in Benzene CC bond order is _______________CC bond order is _______________ C–C single bond = 154 pm C=C bond = 134 pmC–C single bond = 154 pm C=C bond = 134 pm CC bonds in benzene = 139 pmCC bonds in benzene = 139 pm π electrons delocalized

36. 36 © 2009 Brooks/Cole - Cengage Bonding in Benzene

37. 37 © 2009 Brooks/Cole - Cengage Other Aromatic Hydrocarbons TolueneNaphthalene

38. 38 © 2009 Brooks/Cole - Cengage Benzene Derivatives Aniline C 6 H 5 NH 2 Phenol C 6 H 5 OH TNT trinitrotoluene C 6 H 4 CH 3 (NO 2 ) 3

39. 39 © 2009 Brooks/Cole - Cengage Naming Benzene Derivatives 1,4-dimethylbenzene Common name: Para-xylene

40. 40 © 2009 Brooks/Cole - Cengage Reactions of Aromatics SubstitutionsSubstitutions — not additions — are typical. AlCl 3 is a catalyst. Catalysts typically used in aromatic substitutions.

41. 41 © 2009 Brooks/Cole - Cengage Functional Groups See Chemistry Now, Chapter 10

42. 42 © 2009 Brooks/Cole - Cengage Alcohols Characterized by –OH groupCharacterized by –OH group Name: add –ol to name of hydrocarbonName: add –ol to name of hydrocarbon Methanol Butanol

43. 43 © 2009 Brooks/Cole - Cengage Structures of Alcohols C 3 H 5 OH: how many structural isomers? Naming: Add -ol to name of 3-C hydrocarbon. Indicate position of OH with number.

44. 44 © 2009 Brooks/Cole - Cengage Alcohol Properties Alcohols are a derivative of waterAlcohols are a derivative of water Many alcohols dissolve in waterMany alcohols dissolve in water Methanol dissolves in water. Butanol is NOT soluble in water.

45. 45 © 2009 Brooks/Cole - Cengage “Sterno” Alcohols burn in airAlcohols burn in air A mixture of ethanol + calcium acetate = STERNOA mixture of ethanol + calcium acetate = STERNO

46. 46 © 2009 Brooks/Cole - Cengage GLYCOLS Alcohols with Two OH Groups Ethylene glycol

47. 47 © 2009 Brooks/Cole - Cengage Alcohol Reactions Screen 11.6 Substitution Elimination—the reverse of addition PLAY MOVIE

48. 48 © 2009 Brooks/Cole - Cengage TYPES OF ALCOHOLS

49. 49 © 2009 Brooks/Cole - Cengage More Alcohol Reactions Ethanol is a PRIMARY ALCOHOL. It is oxidized to an ALDEHYDE and then to an ACID.

50. 50 © 2009 Brooks/Cole - Cengage More Alcohol Reactions SECONDARY ALCOHOLS are oxidized to KETONES — and reaction stops there.

51. 51 © 2009 Brooks/Cole - Cengage Sugars: Related to Alcohols Sugars are carbohydrates, compounds with the formula C x (H 2 O) y.Sugars are carbohydrates, compounds with the formula C x (H 2 O) y. What is the difference between  and  D-glucose?

52. 52 © 2009 Brooks/Cole - Cengage Sucrose and Ribose Deoxyribose, the sugar in the DNA backbone.

53. 53 © 2009 Brooks/Cole - Cengage AminesAmines Alcohols are derivatives of H 2 O (R–OH) and amines are derivatives of NH 3. Methylamine Dimethylamine Trimethylamine

54. 54 © 2009 Brooks/Cole - Cengage AminesAmines Amines generally have terrible odors! Cadaverine Pyridine

55. 55 © 2009 Brooks/Cole - Cengage AminesAmines Amines, like NH 3, are bases

56. 56 © 2009 Brooks/Cole - Cengage AminesAmines Many natural products and drugs (such as nicotine and cocaine) are bases. Nicotine H+H+H+H+

57. 57 © 2009 Brooks/Cole - Cengage Compounds with Carbonyl Group AldehydeAldehyde Carboxylic acid KetoneKetone

58. 58 © 2009 Brooks/Cole - Cengage Structures of Aldehydes Cinnamaldehyde Odors from aldehydes and ketones

59. 59 © 2009 Brooks/Cole - Cengage Carboxylic Acids Benzoic acid Carboxylic acid group with acidic H + All are WEAK acids Acetic acid Acids are found in many natural substances: bread, fruits, milk, wine

60. 60 © 2009 Brooks/Cole - Cengage Carboxylic Acids Aspirin, acetylsalicylic acid Formic acid, HCO 2 H, gives the sting to ants.

61. 61 © 2009 Brooks/Cole - Cengage Acids + Alcohols --> ESTERS Esters have generally pleasant odors

62. 62 © 2009 Brooks/Cole - Cengage Acids + Alcohols --> ESTERS One of the important reactions in nature!

63. 63 © 2009 Brooks/Cole - Cengage Acids + Alcohols --> ESTERS Many fruits such as bananas and strawberries contain esters.

64. 64 © 2009 Brooks/Cole - Cengage Glycerol Alcohol with 3 OH Groups Combine this with long chain acids f ??? Fatty acids f fats and oils Combine this with long chain acids f ??? Fatty acids f fats and oils

65. 65 © 2009 Brooks/Cole - Cengage Fats and Oils R = organic group with NO C=C bonds C 12 = Lauric acid C 16 = Palmitic acid C 18 = Stearic acid R = organic group with NO C=C bonds C 12 = Lauric acid C 16 = Palmitic acid C 18 = Stearic acid R = organic group WITH C=C bonds C 18 = oleic acid R = organic group WITH C=C bonds C 18 = oleic acid What is the functional group in a fat or oil?

66. 66 © 2009 Brooks/Cole - Cengage Fats and Oils Fats with C=C bonds are usually LIQUDS Oleic acid: a monounsaturated fatty acid C=C bond

67. 67 © 2009 Brooks/Cole - Cengage Fats and Oils Fats with saturated acids (no C=C bonds) are SOLIDS. Saturated fats are more common in animals.

68. 68 © 2009 Brooks/Cole - Cengage Fats and Polar Bears Bears gorge on blubber in the winter.Bears gorge on blubber in the winter. During the summer bears rely on stored fat for energy.During the summer bears rely on stored fat for energy. Burn 1-1.5 kg of fat per day.Burn 1-1.5 kg of fat per day. Water for metabolism comes from fat burning.Water for metabolism comes from fat burning. Bears gorge on blubber in the winter.Bears gorge on blubber in the winter. During the summer bears rely on stored fat for energy.During the summer bears rely on stored fat for energy. Burn 1-1.5 kg of fat per day.Burn 1-1.5 kg of fat per day. Water for metabolism comes from fat burning.Water for metabolism comes from fat burning.

69. 69 © 2009 Brooks/Cole - Cengage Trans Fatty Acids Oleic acid is a mono–unsaturated cis- fatty acidOleic acid is a mono–unsaturated cis- fatty acid Trans fatty acids have deleterious health effects.Trans fatty acids have deleterious health effects. Trans fatty acids raise plasma LDL cholesterol and lower HDL levels.Trans fatty acids raise plasma LDL cholesterol and lower HDL levels. C=C bond

70. 70 © 2009 Brooks/Cole - Cengage Fats and Oils: Saponification

71. 71 © 2009 Brooks/Cole - Cengage Acids + Amines --> AMIDES N-methylacetamide

72. 72 © 2009 Brooks/Cole - Cengage Acids + Amines --> AMIDES Acetaminophen Tylenol, Datril, Momentum,... Acetaminophen

73. 73 © 2009 Brooks/Cole - Cengage Alpha-Amino Acids

74. 74 © 2009 Brooks/Cole - Cengage Peptides and Proteins Adding more peptide links ---> PROTEIN – H 2 O

75. 75 © 2009 Brooks/Cole - Cengage PolymersPolymers Giant molecules made by joining many small molecules called monomersGiant molecules made by joining many small molecules called monomers Average production is 150 kg per person annually in the U.S.Average production is 150 kg per person annually in the U.S.

76. 76 © 2009 Brooks/Cole - Cengage Polymer Classifications Thermoplastics (polyethylene) soften and flow when heatedThermoplastics (polyethylene) soften and flow when heated Thermosetting plastics — soft initially but set to solid when heated. Cannot be resoftened.Thermosetting plastics — soft initially but set to solid when heated. Cannot be resoftened. Other classification: plastics, fibers, elastomers, coatings, adhesivesOther classification: plastics, fibers, elastomers, coatings, adhesives

77. 77 © 2009 Brooks/Cole - Cengage Polymer Preparation Addition polymers — directly adding monomer units togetherAddition polymers — directly adding monomer units together Condensation polymers — combining monomer units and splitting out a small water (water)Condensation polymers — combining monomer units and splitting out a small water (water)

78. 78 © 2009 Brooks/Cole - Cengage Polyethylene: Addition Polymer EthylenePolyethylene A polymer with a molar mass of 1e 6 has about 360,000 units.

79. 79 © 2009 Brooks/Cole - Cengage Mechanism of Addition Polymerization PLAY MOVIE

80. 80 © 2009 Brooks/Cole - Cengage Types of Polyethylene Linear, high density PE (HDPE) Branched, low density PE, LDPE Cross-linked PE, CLPE

81. 81 © 2009 Brooks/Cole - Cengage Types of Polyethylene Table 10.12: others are PVC, acrylonitrile, polypropylene, polymethyl methacrylate

82. 82 © 2009 Brooks/Cole - Cengage Polystyrene Polystyrene is nonpolar material and dissolves in organic solvents.Polystyrene is nonpolar material and dissolves in organic solvents. PS foam is mostly air, and when it dissolves it collapses to a much smaller volume.PS foam is mostly air, and when it dissolves it collapses to a much smaller volume.

83. 83 © 2009 Brooks/Cole - Cengage Slime! Slime is polyvinylalcohol cross-linked with boric acid

84. 84 © 2009 Brooks/Cole - Cengage Bubble Gum! A copolymer Styrene + butadiene

85. 85 © 2009 Brooks/Cole - Cengage Condensation Polymers

86. 86 © 2009 Brooks/Cole - Cengage Polyesters, PET Jackets made from recycled PET soda bottles Soda bottles, mylar film.

87. 87 © 2009 Brooks/Cole - Cengage Polyesters: Mechanism PLAY MOVIE

88. 88 © 2009 Brooks/Cole - Cengage Polyamides: Nylon PLAY MOVIE

89. 89 © 2009 Brooks/Cole - Cengage Polyamides: Nylon Each monomer has 6 C atoms in its chain.Each monomer has 6 C atoms in its chain. A polyamide link forms on elimination of HClA polyamide link forms on elimination of HCl Result = nylon 66Result = nylon 66 Proteins are polyamidesProteins are polyamides

90. 90 © 2009 Brooks/Cole - Cengage Polymer Recycling Symbols LDPE = Low density PE = 0.910-0.925 g/cm 3 HDPE = High density PE = 0.941-0.965 PP = Polypropylene = 0.90 V = PVC (Vinyl chloride) = 1.30-1.58