side of the equilibrium is favored? (Hint: use the pKa data provided in the experimental.) [Note: this is an important proton transfer reaction:recall that in the SN2 displacement, -[Cl-]/-[H+] is really the loss of Et2NH2+/Cl+ (diethylammonium chloride)! Diethylamine therefore acts as both a nucleophile and a base! Diethylamine was supplied in significant excess (5.00 equiv.) for our reaction. Excess amine was used because there must be a lone pair of electrons on nitrogen to act as a nucleophile;this same lone pair is also basic.]
Fig: 1