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Preparing Isopentyl Acetate by the Fischer Esterification

Preparing Isopentyl Acetate by the Fischer Esterification
Leah Monroe
May 8, 2003

Organic Chemistry Lab II
Experiment performed on April 29 and May 1, 2003

Abstract:
The purpose of this experiment was to synthesize isopentyl acetate via an esterification reaction between acetic acid and isopentyl alcohol, using concentrated sulfuric acid as a catalyst. The product was washed with sodium hydrogen carbonate, as well as with water, then dried with anhydrous sodium sulfate. The product was then distilled using a Hickman still and characterized using infrared spectroscopy. The percent yield of isopentyl acetate was 61.52%. This may have been low due to not all of the condensed product being removed from the
Hickman still, some product being lost during transfer of the product from the reaction tube into the Hickman still, or the loss of some product due to evaporation during distillation. Infrared spectrum analysis of the product indicated that the product was isopentyl acetate, as expected, and thus that the reaction was successful.

Preparing Isopentyl Acetate by the Fischer Esterification
Introduction: The purpose of this experiment is to synthesize isopentyl acetate via an esterification reaction between acetic acid and isopentyl alcohol, using concentrated sulfuric acid as a catalyst. The product will be washed, distilled, then characterized using infrared spectroscopy.

Materials Used:
Paraffin
test tube
50-mL Erlenmeyer flask cork microspatula sand bath
Pasteur pipettes
Rubber bulbs

sand bath clamp Hickman still
Pasteur pipettes with bent ends
Kim-wipes
vial

Reagents and Properties:
Formula Weight

Substances

Moles Used Mole Ratio Melting Point
°C

Quantity

g/mol

Acetic Acid

60.05

2 mL

0.0349

1 to 1

Isopentyl acetate

130.19

product

N/A

1 to 1

Isopentyl alcohol
Conc. sulfuric acid
Sodium hydrogen carbonate, 5%

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