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(CHEM 233) Recrystallization Lab Report

Sandra Watson
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UniversityUniversity of Illinois at Chicago

Base Extraction of Benzoic Acid from Acetanilide; Recrystallization of
Methods and Background
Our goal in this lab was to separate benzoic acid and acetanilide from a 1:1 mixture of
the two by extraction using a separatory funnel with di-chloromethane and sodium hydroxide,
and purify them using recrystallization methods. After recrystallization we calculated the
percent yield for any product we may have lost along the way, and ran our crystals through IR
to verify that we purified our samples through corresponding IR peaks. Recrystallization is a
method used to purify compounds that are solid at room temperature instead of distillation or
chromatography which are used for purifying liquids and gases at room temperatures.
This method works by choosing a solvent (like methylene chloride) that will dissolve
both benzoic acid and acetanilide. After dissolving in the separatory funnel, addition of sodium
hydroxide de-protonates benzoic acid and the resulting sodium benzoate and water are formed
as in the reaction shown below.


(CHEM 233) Recrystallization Lab Report


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