Introduction

Objective:

This lab will use multiple different techniques to separate the components of Excedrin.

Your job is to fill out this flow chart appropriately using your knowledge of organic chemistry to determine which compound will go in which box.

Liquid-Liquid Extraction:

A liquid-liquid extraction is a purification technique where two liquid layers separate based on polarity.

We refer to these layers as the organic layer and aqueous layer since this technique is usually done by mixing water with an immiscible organic solvent.

Liquid-liquid extraction can be used as a purification technique because you can use the layer separation and clever use of chemistry to dissolve a desired product into one layer while any unwanted products will go into the other.

A flow chart read from top to bottom. The first box contains the chemical structure of caffeine labeled 1, the chemical structure of aspirin labeled 2, the chemical structure acetaminophen labeled 3, and inactive ingredients labeled 4. To the right of this box is the description 500 m g of Excedrin contains these four compounds. Below the box is the statement, 5 m L ethyl acetate (E T O A C) filter and rinse twice with E T O A C 1 m L plus 1 m L. The arrow from the first box branches to the left and the right. The right path is labeled and leads to an empty box. From this box the path is labeled rinse with acetone 2 m L plus 2 m L plus 2 m L, and splits in two. The right path again is labeled solid and the box it leads to has the letter B inside. The left path is labeled filtrate and has the letter C inside. An arrow from this box, labeled evaporate, leads to a last box with the letter D inside. Returning to the first path split at the beginning the arrow left is labeled filtrate (liquid) and leads to a box with the letters A 1 inside. The path below this box is labeled extract with 1 M K 2 H P O 4, 2 m L plus 2 m L plus 2 m L. This path splits in two. The right split is labeled aqueous and leads to a box with the letter E inside. The path from this box is labeled add 6 M H C L 1.5 m L, and leads to a box with the word observe written inside. The path from this box is labeled filter, and splits in two, one path is labeled solid and leads to a box with the letter F inside, and the other is labeled filtrate and leads to a box with the letter X inside. Returning to the left side path that split from box A 1. The path is labeled organic and leads to a box with the letters A 2 inside. The path below this box is labeled extract with 1 M K O H 2 m L plus 2 m L plus 2 m L, and splits in two. The left path labeled organic leads to a box with the letters A3 inside. The path below this is labeled wash with brine 2 m L and leads to a box with the letter I inside. The path from this box is labeled dry O R G layer with N A 2 S O 4, and filter, and leads to a box with the letter J inside. This box is also labeled filtrate. The path from this box is labeled evaporate and leads to a box with the letter K inside. Returning to the right side path that split from the box A2. The path below this box is labeled aqueous and leads to a box with the letter G inside. The path below this box is labeled add 6 M H C L 1.5 m L, and the box has the word observe written inside. The path from this box is labeled extract with E T O A C three times 2 m L, and splits in two. The lower path is labeled aqueous and leads to a single box. The upper path is labeled organic and leads to a single box. From this box the path is labeled wash with brine, dry O R G layer with N A 2 S O 4, filter and leads to a single box. This box is labeled filtrate. The path from this box is labeled evaporate and leads to a single box with the letter H inside.

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