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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.

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Aromaticity

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  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!!!!!

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