1. Alkenes Properties Nomenclature Stability 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

20. Establish Priority of Substituents on Each sp 2 Carbon

22. What’s My Name?

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

24. Priorities with Multiple Bonds

25. E or Z?

27. Name These

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

30. Enthalpy Change Shows Relative Energy of Alkene

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

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

33. Relative Stabilities of Alkenes

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

37. The Addition Reaction

38. HBr Addition

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

42. Depicting a Reaction

43. Addition of HBr or HCl Markovnikov Addition

44. Regiochemistry Determined by Stability of Intermediate

46. Hyperconjugation

47. Carbocation Stability more highly substituted, lower energy

49. 3 o Carbocation forms Preferentially

53. What Alkenes are Needed to form Theses Alkyl Halides?

54. 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.

55. Determine the major product:

57. Rearrangements

59. Propose a Mechanism

60. 2 Possible pathways to the Carbocation Intermediates

61. Endo- transition state looks like product Exo- transition state looks like Reactant

62. Hammond’s Postulate Related species that are close in energy are close in structure. In an endothermic reaction, the transition state is similar to the product in structure and stability. In an exothermic reaction, the transition state is similar to the reactant in structure and stability. i.e. the structure of the transition state resembles the structure of the most stable species.