Although most simple amines cannot be resolved into enantiomers, several types of chiral amines can be resolved
Quaternary ammonium salts with asymmetric nitrogen atoms
Amines that cannot attain the sp2 hybrid transition state for nitrogen inversion( a small ring).
The pKa of RNH+3 is the pH at which half of the molecules are protonated. At lower (more acidic) pH, the amine is mostly protonated RNH+3 . At
higher (more basic) pH, the amine is mostly deprotonated (RNH2).
Salts of Amines
Protonation of an amine gives an amine salt. The amine salt is composed of two typesof ions: the protonated amine cation (an ammonium ion)
and the anion derived from the acid.
Amine salts are ionic, high-melting, nonvolatile solids. They are much more soluble in water than the parent amines, and they are only slightly
soluble in nonpolar organic solvents
NOTE: Strongly acidic reagents protonate the amino group, giving an ammonium salt that bears a full positive charge. The NH3 group is strongly
deactivating and meta-allowing
Alkylation of amines can give good yields of the desired alkylated products in two types of reactions:
with acidic
Problem-solving Hint
The key to solving Hofmannelimination problems is to find allpossible ways the compound caneliminate. Then, the one that gives
the least substituted alkene is probably favored
Because of the many competing reaction pathways, alkanediazoniums alts usually decompose to give complex mixtures of products. Therefore,
the diazotization of primary alkylamines is not widely used for synthesis
Secondary N-nitrosoamines are stable under the reaction conditions because they do not have the NH proton needed for the tautomerism.
Primary Amines
Secondary Amines
Tertiary Amines
The reducing agent mustreduce the iminium salt, but it must not reduce the carbonyl group of the ketone or Aldehyde becz Iminium salts are
frequently unstable, so they are rarely isolated
Gabriel Synthesis