Experiment 14A: Isopentyl Acetate

In this experiment, the synthesis of isopentyl acetate via the Fischer esterification of acetic acid with isopentyl alcohol was studied.1 Sulfuric acid acted as a catalyst for the reaction. A large excess of acetic acid and the addition of heat to the system shifted the reaction’s equilibrium to the right, favoring the ester. The percent yield was 227%, most likely due to weighing errors. H1 NMR, C13 NMR, and C13 DEPT NMR spectra were taken to confirm the product. The peaks, integrations, and spin-spin splitting on the H1 NMR indicated that the molecule was isopentyl acetate. The peaks of the C13 and C13 DEPT NMR spectra also corresponded to the structure of isopentyl acetate, although the peak resulting from the carbonyl carbon was not clearly identifiable. In light of this data, as well as the product's strong banana-like odor, it was concluded that the product did in fact contain isopentyl acetate, though the purity of the compound could not be determined.