1 / 31

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.

zanna
Download Presentation

Chapter 16 Discussion

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  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?

More Related