Charges in nucleophilic substitution reactions
In all reactions the total charge on products equals the total charge on reactants.
This means that the products from a substitution reaction involving
Cations bearing H at positive O or N are strong acids and donate H+ during reaction work-up.
Thus reaction of alkyl halides by substitution with
The charges on the products above are consistent with changes in "electron ownership", that is
This means that the products from a substitution reaction involving
a molecular nucleophile and molecular substrate are a cation and an anion
(1).
a cation substrate and an anion nucleophile are two molecules.
(1).a cation substrate and an anion nucleophile are two molecules.
Cations bearing H at positive O or N are strong acids and donate H+ during reaction work-up.
Thus reaction of alkyl halides by substitution with
water (HOH) gives ROH2+ and then alcohols (ROH) after work-up
alcohols (ROH) gives R2OH+ and then ethers (ROR) after work-up
amines (primary or secondary) or ammonia gives amines (RNH2, R2NH or R3N)
alcohols (ROH) gives R2OH+ and then ethers (ROR) after work-up
amines (primary or secondary) or ammonia gives amines (RNH2, R2NH or R3N)
The charges on the products above are consistent with changes in "electron ownership", that is
the atom in the nucleophile that is bonded to carbon in the product is one unit more positive because it "owns" one fewer electrons.
the atom displaced from the substrate is one unit more negative because in the product it "owns" one more electron.
the atom displaced from the substrate is one unit more negative because in the product it "owns" one more electron.