The sulfuric acid catalyzed Fischer esterification of isopentyl alcohol and acetic acid provided the product isopentyl acetate in 25% yield as a clear liquid.
The purity of the product was determined via ultra-micro boiling point analysis. The boiling point of the isopentyl acetate was found to be 140°C. The similarity of the experimental boiling point to the literature value allows for determination of the product identity.The IR spectrum of the isopentyl acetate allows for further confirmation of the product identity, including a lack of contamination by water or isopentyl alcohol, as no peak was observed above 3000 cm-1. The low percent yield could be a result of the initial equilibrium not being shifted to the products strongly enough; a problem that, according to Le Chatlier’s principle, could have been mitigated by increasing the concentration of the reactants.
The reaction yield could also have been lessened by the loss of some product due to evaporation during distillation, or by the possibility that some of the product re-converted to the reactants when the acid was neutralized with sodium bicarbonate. The reaction yield could be improved by employing a thin layer chromatography prior to the addition of sodium bicarbonate. This would ensure that the reaction was complete. Reference 1. Aldrich Handbook of Fine Chemicals, 2003-2004.