Discussion: amines

Amine nomenclature diisopropylaminepyrrole 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 N How do you improve selectivity??

Still mixture Need 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)?

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