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Discussion: amines

Discussion: amines. Amine nomenclature. diisopropylamine. pyrrole. pyrrolidine. histamine. nicotine. Formation of amines. triethylamine. Mechanism for LAH reduction of amides. 1-methylpiperidine. One equivalent . SN2 is faster the more R groups on N How do you improve selectivity??.

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Discussion: amines

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  1. Discussion: amines

  2. Amine nomenclature diisopropylamine pyrrole pyrrolidine histamine nicotine

  3. Formation of amines triethylamine

  4. Mechanism for LAH reduction of amides

  5. 1-methylpiperidine

  6. One equivalent SN2 is faster the more R groups on N How do you improve selectivity??

  7. Still mixture Need a base to remove protons to get to quaternary product

  8. Poor selectivity save for quaternary product and for primary amines from ammonia.

  9. Only good for primary amines

  10. Reduction of nitriles with LiAlH4: MECHANISM

  11. Gabriel Synthesis of primary amines

  12. Product(s)? Name?

  13. Reactions of Amines • Acid-base • Formation of amide • Imines and enamines • Formation of urea from isocyanate • Hoffmann elimination and substitution reactions

  14. Higher the pKa of conjugate acid, the more basic the amine Which is the weakest base? Which is the strongest base?

  15. Which conjugate base is more basic (stronger)?

  16. Which conjugate base is more basic (stronger)?

  17. Based on the pKa of imidazolium ion above, describe the what the imidazole group in the histidine residue in a peptide would be under physiological conditions (pH 7).

  18. Formation of amide

  19. Acetamides

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