Ch18 Amines(pdf) - KFUPM Open Courseware

Gabriel Synthesisgives primary amines without formation ofsecondary, etc. amines as byproductsuses an S N 2 reaction on an alkyl halide to formthe C—N C N bondGabriel Synthesisgives primary amines without formation ofsecondary, etc. amines as byproductsuses an S N 2 reaction on an alkyl halide to formthe C—N C N bondthe nitrogen-containingnucleophileis N-potassiophthalimidethe nitrogen-containingnucleophileis N-potassiophthalimideO–•• N ••K +ON-PotassiophthalimideN-Potassiophthalimideas a nucleophilethe pKa of phthalimide is 8.3N-potassiophthalimideis easily prepared bythe reaction of phthalimide with KOHO•• NHOKOHO–•• N • OK +O•• N– •••• + R X ••••OS N 2+O••N RO•• –X •• •• ••