The nucleophilic properties of amines

The nucleophilic properties of amines Why do amines act as nucleophiles? A nucleophile is something which is attracted to, and then attacks, a positive or slightly positive part of another molecule or ion. All amines contain an active lone pair of electrons on the very electronegative nitrogen atom. It is these electrons which are attracted to positive parts of other molecules or ions. The reactions of primary amines with halogenoalkanes You get a complicated series of reactions on heating to give a mixture of products - probably one of the most confusing sets of reactions you will meet at this level. The products of the reactions include secondary and tertiary amines and their salts, and quaternary ammonium salts. Making secondary amines and their salts In the first stage of the reaction, you get the salt of a secondary amine formed. For example if you started with ethylamine and bromoethane, you would get diethylammonium bromide In the presence of excess ethylamine in the mixture, there is the possibility of a reversible reaction. The ethylamine removes a hydrogen from the diethylammonium ion to give free diethylamine - a secondary amine. Making tertiary amines and their salts But it doesn't stop here! The diethylamine also reacts with bromoethane - in the same two stages as before. This is where the reaction would start if you reacted a secondary amine with a halogenoalkane. In the first stage, you get triethylammonium bromide. There is again the possibility of a reversible reaction between this salt and excess ethylamine in the mixture. The ethylamine removes a hydrogen ion from the triethylammonium ion to leave a tertiary amine - triethylamine. Making a quaternary ammonium salt The final stage! The triethylamine reacts with bromoethane to give tetraethylammonium bromide - a quaternary ammonium salt (one in which all four hydrogens have been replaced by alkyl groups). This time there isn't any hydrogen left on the nitrogen to be removed. The reaction stops here.