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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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amine nomenclature
Amine nomenclature

diisopropylamine

pyrrole

pyrrolidine

histamine

nicotine

formation of amines
Formation of amines

triethylamine

slide6

One equivalent

SN2 is faster the more R groups on N

How do you improve selectivity??

slide7

Still mixture

Need a base to remove protons to get to quaternary product

reactions of amines
Reactions of Amines
  • Acid-base
  • Formation of amide
  • Imines and enamines
  • Formation of urea from isocyanate
  • Hoffmann elimination and substitution reactions
slide19

Higher the pKa of conjugate acid, the more basic the amine

Which is the weakest base?

Which is the strongest base?

slide22

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).