Nucleophilic Aromatic Substitution—Addition and Identification of an Amine

The addition of a nucleophilic functional group to an electron-deficient aromatic ring is a versatile reaction in the modern organic chemistry arsenal. The proper positioning of a leaving group on this ring effectively allows for a substitution reaction to occur. A 3 h laboratory experiment is described in which students utilize a common electrophilic aromatic ring and affect a substitution with an unknown amine, the identity of which is later characterized by the melting point and 1 H NMR spectrum of the product.