1. Philip Dutton University of Windsor, Canada N9B 3P4 Prentice-Hall © 2002 General Chemistry Principles and Modern Applications Petrucci Harwood Herring 8 th Edition Chapter 27: Organic Chemistry

2. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 2 of 75 Contents 27-1Organic Compounds and Structures: An Overview 27-2Alkanes 27-3Alkenes and Alkynes 27-4Aromatic Hydrocarbons 27-5Alcohols, Phenols, and Ethers 27-6Aldehydes and Ketones 27-7Carboxylic Acids and Their Derivatives 27-8Amines 27-9Heterocyclic Compounds

3. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 3 of 75 Contents 27-10Nomenclature of Stereoisomers in Organic Compounds 27-11An Introduction to Substitution Reactions at sp 3 Hybridized Carbon Atoms 27-12Synthesis of Organic Compounds 27-13Polymerization Reactions Focus On Natural and Synthetic Dyes

4. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 4 of 75 27-1 Organic Compounds and Structures: An Overview Hydrocarbons – the simplest organic compounds. Simplest hydrocarbon is methane.

5. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 5 of 75 Ethane

6. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 6 of 75 Skeletal Isomerism Prentice Hall © 2002 General Chemistry: Chapter 27 Slide 5 of

7. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 7 of 75 Simplified Drawings of Organic Structures

8. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 8 of 75 Nomenclature Select the longest continuous carbon chain. –This determines the base name. Consider each branch and name similarly except change the name from –ane to –yl. Number the C atoms so that substituents have the lowest possible number.

9. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 9 of 75 Nomenclature Name each substituent according to its identity and the number of the C atom to which it is attached. –Use di, tri, tetra as appropriate. Separate numbers from one another by commas. List substituents alphabetically by name.

10. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 10 of 75 Table 27.1. Some Common Alkyl Groups

11. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 11 of 75 Positional Isomerism

12. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 12 of 75 Functional Groups

13. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 13 of 75 Functional Groups

14. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 14 of 75 27-2 Alkanes

15. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 15 of 75 Conformations

16. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 16 of 75 Ring Structures

17. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 17 of 75 Ring Strain

18. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 18 of 75 Cyclohexane Conformations

19. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 19 of 75 Preparation of Alkanes CH 2 =CH 2 + H 2 → CH 3 -CH 3 Pt Δ 2 CH 3 CH 2 Br + 2 Na → CH 3 CH 2 CH 2 CH 3 + 2 NaBr pressure Δ

20. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 20 of 75 Reactions of Alkanes Initiation:Cl-Cl → 2 Cl· Propagation:H 3 C-H + Cl· → H 3 C· + HCl H 3 C· + Cl 2 → H 3 C-Cl + Cl· Termination: H 3 C· + Cl· → H 3 C-Cl Cl· + Cl· → Cl-Cl H 3 C· + H 3 C· → H 3 C-CH 3 Δ or h

21. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 21 of 75 Combustion Reactions C 8 H 18 (l) + O 2 (g) → 8 CO 2 (g) + 9 H 2 O(l) 25 2 ΔH° = -5.48  10 3 J

22. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 22 of 75 Table 27.4 Principle Petroleum Fractions

23. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 23 of 75 Octane Number

24. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 24 of 75 27-3 Alkenes and Alkynes

25. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 25 of 75 Geometric Isomerism

26. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 26 of 75 Elimination Reaction

27. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 27 of 75 Addition Reactions Markovnikov rule

28. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 28 of 75 Hydration Reaction Addition is favored in dilute acid and elimination is favored in strong.

29. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 29 of 75 Reduction of C=C

30. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 30 of 75 27-4 Aromatic Hydrocarbons

31. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 31 of 75 Characteristics of Aromatic Hydrocarbons Planar (flat) cyclic molecules. Conjugated п systems (4n + 2)

32. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 32 of 75 Naming Aromatic Hydrocarbons

33. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 33 of 75 Aromatic Substitution Reactions

34. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 34 of 75 Aromatic Subsitution Reactions

35. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 35 of 75 27-5 Alcohols, Phenols, and Ethers

36. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 36 of 75 Preparation and Use of Alcohols CO(g) + 2 H 2 (g) → CH 3 OH(g) 350 ° C 200 atm ZnO, Cr 2 O 3

37. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 37 of 75 Preparation and Use of Alcohols Methanol. –21 st amongst industrial chemicals. Ethanol. –fermentation or by hydration of ethylene. Ehylene glycol. –High boiling point, soluble in water. Glycerin.

38. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 38 of 75 Ethers

39. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 39 of 75 Aldehydes and Ketones

40. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 40 of 75 Preparation and Use Oxidation of alcohols. Extract from natural sources Acetone is extensively used as a solvent.

41. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 41 of 75 Addition Reactions of the Carbonyl Group

42. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 42 of 75 27-7 Carboxylic Acids and Their Derivatives

43. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 43 of 75 Oxidation of Alcohols CH 3 CH 2 OH + KMnO 4 → CH 3 CO 2 - K + → CH 3 CO 2 H OH - H+H+

44. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 44 of 75 Aromatic Acids

45. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 45 of 75 Acetyl Group

46. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 46 of 75 Esters

47. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 47 of 75 Amides

48. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 48 of 75 Resonance in Amides

49. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 49 of 75 Reduction Reactions

50. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 50 of 75 Amines

51. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 51 of 75 Preparation of Amines 2 NH 3 + CH 3 Br → CH 3 NH 3 + Br - + NH 3 → CH 3 NH 2 + NH 4 Br

52. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 52 of 75 Basicity of Amines

53. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 53 of 75 Ammonium Salts

54. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 54 of 75 27-9 Heterocyclic Compounds

55. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 55 of 75 27-10 Nomenclature of Stereoisomers in Organic Compounds

56. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 56 of 75 Chirality

57. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 57 of 75 The R,S System of Nomenclature Substituent of higher atomic number takes precedence over one of lower atomic number:

58. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 58 of 75 The R,S System of Nomenclature If two substituents attached to the stereocenter have the same priority, proceed along the chains to the first point of difference:

59. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 59 of 75 The R,S System of Nomenclature Double and triple bonds count as if they were single and the atoms are duplicated or triplicated at the other end of the double or triple bond:

60. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 60 of 75 The E,Z System of Nomenclature

61. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 61 of 75 The E,Z System of Nomenclature

62. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 62 of 75 27-11 An Introduction to Substitution Reactions at sp 3 Hybridized Carbon

63. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 63 of 75 S N 2 Mechanism Rate = k[OH - ][CH 3 Cl]

64. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 64 of 75 Inversion of Configuration

65. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 65 of 75 S N 1 Mechanism

66. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 66 of 75 S N 1 Mechanism Rate = k [(CH 3 ) 3 CCl]

67. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 67 of 75 Racemic Products From S N 1 Reactions

68. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 68 of 75 27-12 Synthesis of Organic Compounds

69. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 69 of 75 27-13 Polymerization Reactions

70. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 70 of 75 Table 27.5 Some Polymers Produced by Chain-Reaction Polymerization

71. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 71 of 75 Condensation Polymerization

72. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 72 of 75 Table 27.6 Some Polymers Produced by Step Reaction Polymerization

73. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 73 of 75 Stereospecific Polymers

74. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 74 of 75 Focus On Natural and Synthetic Dyes

75. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 75 of 75 Focus On Natural and Synthetic Dyes

76. Prentice-Hall © 2002General Chemistry: Chapter 27Slide 76 of 75 Chapter 27 Questions Develop problem solving skills and base your strategy not on solutions to specific problems but on understanding. Choose a variety of problems from the text as examples. Practice good techniques and get coaching from people who have been here before.