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Chapter 16 Discussion

Chapter 16 Discussion. Synthesis problem. Conjugation. How to prepare dienes ?. How to prepare dienes ?. Retrosynthetic analysis. Retrosynthetic analysis. Synthesis plan. Reactions of conjugated dienes. 1,2- and 1,4 addition of HX and X 2 Polymerization Diels Alder cycloaddition.

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Chapter 16 Discussion

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  1. Chapter 16 Discussion

  2. Synthesis problem

  3. Conjugation

  4. How to prepare dienes?

  5. How to prepare dienes?

  6. Retrosynthetic analysis

  7. Retrosynthetic analysis Synthesis plan

  8. Reactions of conjugated dienes 1,2- and 1,4 addition of HX and X2 Polymerization Diels Alder cycloaddition

  9. Addition of HX to dienes kinetic thermodynamic

  10. Addition of X2 to dienes kinetic thermodynamic

  11. Diels-Alder Cycloadditions: one-step preparation of cyclohexenes

  12. ? Recognize that this is a Diels Alder reaction by the diene and dienophile (on the right) 2) Draw a cyclohexene ring 3) Build models of the possible isomers that could result from the cycloaddition 4) Use resonance to help predict regioisomer 5) Temperature for endo/exo preference.

  13. diene dienophile Recognize that this is a Diels Alder reaction by the diene and dienophile (on the right) 2) Draw a cyclohexene ring 3) Build models of the possible isomers that could result from the cycloaddition 4) Use resonance to help predict regioisomer 5) Temperature for endo/exo preference.

  14. endo exo 3) Build models of the possible isomers that could result from the cycloaddition 4) Use resonance to help predict regioisomer 5) Temperature for endo/exo preference.

  15. Endo and exo + enantiomer + enantiomer Exo (thermodynamic product) Endo (kinetic product)

  16. ? Recognize that this is a Diels Alder reaction by the diene and dienophile (on the right) 2) Draw a cyclohexene ring 3) Build models of the possible isomers that could result from the cycloaddition 4) Use resonance to help predict regioisomer 5) Temperature for endo/exo preference.

  17. Four possible regioisomers and diastereomers (+ enantiomers)

  18. Resonance contributors show which regioisomers will form

  19. Regiochemistry is established. How about endo or exo?

  20. Problem:Diels-Alder Reactants?

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