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Alkenes. Properties Nomenclature Addition Reactions. Ethylene. Electron Rich p -Bond. Cis and Trans no rotation about p -bond. Elements or Degrees of Unsaturation: p -Bond or Ring. Halogens replace Hydrogens. Saturated compounds with Oxygen and Nitrogen.

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Alkenes


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    Presentation Transcript
    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

    8. Determine the # elements of Unsaturation

    9. Alkene Nomenclature

    10. Cyclic alkenes

    11. Alkyl Groups with p-Bonds

    12. Alkylidene GroupsDouble Bonds Fused to Rings

    13. Polyenes

    14. Name these Alkenes

    15. cis-trans Isomers

    16. E/Z System

    17. What’s My Name?

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

    19. Establish Priority of Substituents on Each sp2 Carbon

    20. Priorities with Multiple Bonds

    21. E or Z?

    22. E or Z?

    23. Name These

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

    25. Hydrogenation Data Helps to Determine StabilityDHhydrogenation of Alkenes

    26. Enthalpy Change Shows Relative Energy of Alkene

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

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

    29. Relative Stabilities of Alkenes

    30. Hyperconjugationp bond associates with adjacent C-H s bond

    31. The Addition Reaction

    32. HBr Addition

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

    34. Addition of HBr or HClMarkovnikov Addition

    35. Regiochemistry Determined by Stability of Intermediate

    36. 3o Carbocation forms Preferentially

    37. Carbocation Stabilitymore highly substituted, lower energy

    38. Asymmetric Center is Generated Racemic Mixture Formed

    39. 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.

    40. Determine the major product:

    41. Rearrangements

    42. HBr Addition with RO-ORAnti-Markovnikov

    43. Free-Radical Mechanism