1. Alkenes Properties Nomenclature Addition Reactions

2. Ethylene

3. Electron Rich p-Bond

4. Cis and Transno rotation about p-bond

5. Elements or Degrees of Unsaturation: p-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 p-Bonds

14. Alkylidene GroupsDouble 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 sp2 Carbon

24. Priorities with Multiple Bonds

25. E or Z?

26. 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 StabilityDHhydrogenation 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. Hyperconjugationp bond associates with adjacent C-H s bond

37. The Addition Reaction

38. HBr Addition

39. Markovnikov’s RuleThe 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 HClMarkovnikov Addition

41. Regiochemistry Determined by Stability of Intermediate

42. 3o Carbocation forms Preferentially

43. Carbocation Stabilitymore 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-ORAnti-Markovnikov

50. Free-Radical Mechanism