Download - Discussion: amines
Discussion: amines
Amine nomenclature
diisopropylamine pyrrole
nicotine histamine pyrrolidine
Formation of amines
triethylamine
Mechanism for LAH reduction of amides
1-methylpiperidine
One equivalent
SN2 is faster the more R groups on NHow do you improve selectivity??
Still mixtureNeed a base to remove protons to get to quaternary product
Poor selectivity save for quaternary product and for primary amines from ammonia.
Only good for primary amines
Reduction of nitriles with LiAlH4: MECHANISM
Gabriel Synthesis of primary amines
Name?
Product(s)?
Reactions of Amines
• Acid-base• Formation of amide• Imines and enamines• Formation of urea from isocyanate• Hoffmann elimination and substitution
reactions
Higher the pKa of conjugate acid, the more basic the amine
Which is the strongest base? Which is the weakest base?
Which conjugate base is more basic (stronger)?
Which conjugate base is more basic (stronger)?
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).
Formation of amide
Acetamides