Isopentyl acetate, "banana oil", is a naturally occurring compound that possesses a distinctive odor. It is found in bananas, as well as many other organisms.
This experiment attempts to produce isopentyl acetate by refluxing isopentyl alcohol with acetic anhydride and an acid catalyst. The product is isolated using a combination of techniques -- acid-base extraction, drying, and distillation -- and is characterized by its boiling temperature, IR and NMR spectra, and gas chromatographic (GC) behavior.
Time required: 2 laboratory sessions.