1. Alkenes Properties Nomenclature Addition Reactions

2. Ethylene

3. Electron Rich  -Bond

4. Cis and Trans no rotation about  -bond

5. Elements or Degrees of Unsaturation:  -Bond or Ring

6. Halogens replace Hydrogens

7. Saturated compounds with Oxygen and Nitrogen

9. Determine the # elements of Unsaturation

10. Alkene Nomenclature

12. Cyclic alkenes

13. Alkyl Groups with  -Bonds

14. Alkylidene Groups Double Bonds Fused to Rings

15. Polyenes

16. Name these Alkenes

17. cis-trans Isomers

18. E/Z System

19. What’s My Name?

20. (Z)-4-ethyl-5-isopropyl-4-nonene

22. Establish Priority of Substituents on Each sp 2 Carbon

24. Priorities with Multiple Bonds

25. E or Z?

27. Name These

29. Preparation of Alkenes E2 - Elimination reactions of alkyl halides and tosylates (or mesylates) E1 - Acid catalyzed dehydration of alcohols

30. Hydrogenation Data Helps to Determine Stability  H hydrogenation of Alkenes

31. Enthalpy Change Shows Relative Energy of Alkene

32. Both cis and trans 2-Butene are Hydrogenated to Butane

33. “E” is More Stable than “Z” by 2.3 KJ/mol

34. Relative Stabilities of Alkenes

36. Hyperconjugation  bond associates with adjacent C-H  bond

37. The Addition Reaction

38. HBr Addition

39. Markovnikov’s Rule The addition of H-X across a double bond results in the more highly substituted alkyl halide as the major product.

40. Addition of HBr or HCl Markovnikov Addition

41. Regiochemistry Determined by Stability of Intermediate

42. 3 o Carbocation forms Preferentially

43. Carbocation Stability more highly substituted, lower energy

44. Asymmetric Center is Generated Racemic Mixture Formed

45. Definitions Regioisomers – two constitutional isomers that could result from an addition reaction. Regiospecific – only one regiosisomer forms at the expense of the other. Regioselective – both regioisomers are formed, but one is formed in preference.

46. Determine the major product:

48. Rearrangements

49. HBr Addition with RO-OR Anti-Markovnikov

50. Free-Radical Mechanism

51. Addition of Br 2

52. More Definitions Stereospecific – only one stereoisomer is formed at the expense of the other (e.g. trans vs. cis) Stereoselective – one stereoisomer is formed preferentially over the other.

53. Anti-Addition Stereospecific Reaction Anti-addition

54. Bromonium Ion Intermediate

55. Trans is formed exclusively No Meso is formed (cis)

56. Bromonium Ion is Opened Equally from Both Sides

57. Brominations Often Generate Asymmetric Centers

58. trans alkene + anti addition = MESO

59. Provide a Mechanism

60. Halohydrin Formation Addition of Br – OH Stereospecific & Regiospecific

61. Unsymmetrical Bromonium ion H 2 O opens ring at more hindered site

62. Br and OH are trans in anti addition

63. Catalytic Hydrogenation syn addition

64. Mechanism

65. Syn Addition of H 2

66. Reactions that Generate Chirality Centers Hydrogenation, syn

67. Hydrogenation all alkene  bonds are reduced

68. Asymmetric Induction

69. Preparation of (L)-Dopa for Treatment of Parkinson’s

70. 10 pt. problem 7.(10) Consider the compound 3(S),5,5- trimethylcyclohexene. Upon reduction with H 2 on a 1% Pt/C catalyst, the resulting product has an absolute configuration of (R). Draw the equation for this reaction, clearly drawing the starting alkene and the product alkane and explain why the absolute configuration is completely inverted in this reaction.

71. Hydration Addition of H 2 O

72. Oxymercuration Hydration Markovnikov addition Regiospecific Reaction

73. Oxymercuration Mechanism

74. Hydroboration Hydration Anti-Markovnikov Syn addition

75. Hydroboration

76. Draw the Major Products

77. 2 Complementary Hydration Reactions

78. Cyclopropanation

79. Simmons-Smith Reaction

80. In situ Preparation of Carbene

81. Two MCAD Inhibitors

82. MCPA and SPA

84. Ozonolysis Alkene Cleavage

85. Mechanism of Ozonolysis

86. Addition polymers

87. Air Pollution Reacts with Tires

88. O 3 reacts with all alkene  Bonds

89. Problem An unknown compound A, C 8 H 16, reacts with H 2 on a 1% Pt/C catalyst to form B (C 8 H 18 ). B has two chiral centers but is optically inactive due to the presence of an internal plane of symmetry. Treatment of A with O 3 followed by Zn/HOAc affords butanone only. Identify A and B and draw B in a Fischer projection.

91. What is the Structure of Limonene? Solomons 8.39

92. C=C bonds become carbonyl groups

93. Acid Catalyzed Dimerization Solomons 8.58

94. Hoffmann Product via E1