1 / 85

Aromaticity

Aromaticity. 6-pi electrons in the cyclic planar system, as one lone electron pair of S is not on the sp 2 orbital but on the unhybridized p orbital along the ring. EXTRA D-I-Y PROBLEMS. EAS: REACTIONS of Aromatics. BROMINATION/CHLORINATION. BROMINATION/CHLORINATION. NITRATION.

kaiya
Download Presentation

Aromaticity

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. Aromaticity

  2. 6-pi electrons in the cyclic planar system, as one lone electron pair of S is not on the sp2 orbital but on the unhybridized p orbital along the ring

  3. EXTRA D-I-Y PROBLEMS

  4. EAS: REACTIONS of Aromatics

  5. BROMINATION/CHLORINATION

  6. BROMINATION/CHLORINATION

  7. NITRATION

  8. NITRATION

  9. SULFONATION

  10. SULFONATION

  11. FRIEDEL-CRAFTS ALKYLATION

  12. FRIEDEL-CRAFTS ALKYLATION

  13. FRIEDEL-CRAFTS ALKYLATION LIMITATIONS!!!!

  14. FRIEDEL-CRAFTS ALKYLATION • Another limitation is that the reaction is hard to control and alkylates more than once. • CARBOCATION rearrangement happens here too! • This can be avoided by a 2-step synthesis starting from FRIEDEL-CRAFTS ACYLATION

  15. FR-CR ACYLALTION

  16. FR-CR ACYLALTION

  17. FR-CR ACYLALTION • By using REDUCTION via H2, Pd / Ethanol after, we can make it an alkyl group

  18. FR-CR ACYLALTION • We ALSO AVOID LOSING CONTROL OF ACYLATION, UNLINK IN ALKYLATION WHERE IT ADDS MULTIPLE TIMES. IT ONLY ADDS ONCE, PER REACTION

  19. REDUCTION OF NO2/C=O GROUP NOTE: ONLY THE C=O NEXT TO THE AROMATIC RING CAN BE REDUCED TO THE CH2!!!!!

More Related