A chemist wishes to separate a three-component mixture dissolved in diethyl ether
CHEMISTRY · Multi-part · AP · Chemistry · Properties of Substances and Mixtures · Properties of Substances and Mixtures
Problem
A chemist wishes to separate a three-component mixture dissolved in diethyl ether. The mixture contains benzoic acid (C6H5COOH), aniline (C6H5NH2), and naphthalene (C10H8). The chemist has access to 1.0 M aqueous HCl, 1.0 M aqueous NaHCO3, and standard laboratory glassware.
Answer the prompts below.
(a) For each component of the mixture, classify it as acidic, basic, or neutral in water at 25 °C and briefly justify your classification.
(b) Propose a step-by-step liquid–liquid extraction scheme that will completely separate the three compounds. Your procedure should specify the order in which the aqueous reagents are used and identify in which layer (aqueous or organic) each compound resides after every extraction.
(c) For each extraction step in part (b), write a net ionic equation that shows the acid–base reaction responsible for transferring the target compound between phases.
(d) After carrying out the extractions, describe how each compound can be recovered in pure form from the layer in which it resides. Include any additional reagents or operations required.