Isopentyl acetate was synthesized in 44.9% yield through a reaction between isopentyl alcohol and acetic acid, with sulfuric acid as a catalyst. Identify and purity of the product was confirmed by infrared spectrum analysis of the product and the boiling point (141-142˚C) to the published value of (lit1142.5 ˚C).
Procedure:
Isopentyl alcohol (.893g), acetic acid (2ml), and concentrated sulfuric acid (4 drops) was added to a 5ml conical vial, and then attached to a reflux apparatus. The mixture was heated and allowed to reflux for sixty minutes resulting in pale light brown color. The mixture was cooled to room temperature, before slowly washing with 5% sodium bicarbonate (1ml) three times removing the aqueous after each wash. The drying agent (sodium sulfate) was added to the crude isopentyl acetate left in conical vial and sealed for day 2.
On day two the crude mixture (.983g) with a pale yellow color was moved from the drying agent and into a 3ml conical vial before being connected to a simple distillation apparatus. The crude material was distilled into a clear liquid (.593g) and removed from the still to a vial.
Discussion
The reaction provided the product of isopentyl acetate in 44.9% yield as a clear, banana-scented liquid. The purity of the product was determined by ultramicro boiling point determination and an infrared spectrum analysis. The boiling point was measured at 141-142˚C (lit1 142.5 ˚C) the narrow range of the boiling point indicates the purity of the product.
The infrared spectrum of the product confirmed that the product was isopentyl acetate. A peak at 1743.10 cm-1 showed the presence of a carbonyl group, a characteristic of an ester. The peak at 2961.18 cm-1 indicates a stretch C-H bond and the C-O bond are visible at 1244.20 and 1055.33 cm-1. The peaks confirmed the characteristics of isopentyl acetate.
The reaction was a successful despite the low yield of 44.9%. A significant portion of the product was lost