In this experiment we used a Dean-Stark Apparatus a high molecular weight Dowex

Question

In this experiment we used a Dean-Stark Apparatus a high molecular weight Dowex resin as an acid-catalyst, Acetic acid, and 1-butanol to perform a nucleophillic substitiution. An alcohol will replace the OH of the carboxylic acid to produce an ester. The acid catalyst is removed via filtration.An IR spectrum was obtained to verify purfity.

Propose a numbered, stepwise procedure to isolate the final organic product if you had instead performed the reaction using conc.H2SO4 (l) as the acid catalyst. You may use any reagents, glassware and lab equipment used in previous experiments this or last semester.

Explanation / Answer

In a round bottom flask add acetic acid, 1-butanol followed by addition of few drops of H2SO4 used as catalyst for reaction, reflux for overnight. Cool to room temperature and pour it in water and aqueous layer is extracted with ethylacete. Combined organic layer wash with aq. sodium bicarbonate solution to remove acid impurity. Organic layer dried over sodium sulphate and evaporated under vacuum. Yields butyl acetate (ester)

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