The sulfuric acid catalyzed reaction of isopentyl alcohol with acetic acid to fo

Question

The sulfuric acid catalyzed reaction of isopentyl alcohol with acetic acid to form isopentyl acetate is erformed. This reaction does not proceed to completion. After the reaction is heated under reflux for an our, the product mixture is washed with aqueous sodium bicarbonate solution, the organic layer is dried and purified via distillation, and the organic layer is then analyzed via gas chromatography, GC. Assuming that the GC separation is based only on boiling point, select the compound that will exit the GC column first. Boiling point, 118 O acetic acid O water O isopentyl acetate O sulfuric acid O isopentyl alcohol acetic acid isopentyl acetate |142 isopentyl alcohol 130 sulfuric acid water 290 100

Explanation / Answer

Isopentyl alcohol will come as first compound. Because water will go while we do NaHCO3 workup. along with Acetic acid and sulfuric acid also will go. Hence organic layer have isopentyl acetate and slightly unreacted isopentyl alcohol.

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