Explain step-by-step procedures for conducting this experiment using organic che

Question

Explain step-by-step procedures for conducting this experiment using organic chemistry lab techniques. Please help me find out how I should conduct this experiment if I got such scenario in the lab. I need a step by step procudere and also need clarification on the extraction part where which layer would be what (bottom layer vs top layer). I have issues with understanding the layers and finding out which one is which. Scenario: An organic chemistry student was attempting to synthesize m-chlorobenzoic acid from m-chlorophenol and the reaction did not go to completion and the student ended up with a mixture of both compounds. Purify the m-chlorobenzoic acid. Provide data to show that your compound is pure. Materials Available in the Lab: Solvents: acetone, ethanol, methanol, ethyl acetate, hexanes, dichloromethane. Aqueous Solutions: 1 M NaOH, 1 M HCl, 3 M NaOH, 3 M HCl, 1 M NaHCO3, saturated NaCl. Drying Agent: sodium sulfate Special Glassware: TLC chambers and plates, separatory funnels

Explanation / Answer

For this separation of phenol and acid we have to do 2 extractions.

First extraction.

Take reaction mixture in separatory funnels, dissolve in ethyl acetate and the add water. Followed by add 1 M NaHCO3 solution. Extract well. Lower aqueous layer contains sodium salt of carboxylic acid derivative and organic layer contain phenol. Separated aqueous layer acidify with 1 M HCl and filter the precipitated compound, you will get your pure acid derivative.

Scecond extraction.

Take Organic layer in the separatory funnels and add water and add 1M NaOH and extract well. The all phenol will come in lower aqueous layer as sodium salt. Just separate lower aqueous layer and acidify with 1 M HCl. Again take this aqueous mixture in separatory funnel and add ethyl acetate extract the all pure phenol will come in organic layer and separate the organic layer and dried over sodium sulfate and evaporate under reduced pressure to get the pure phenol.

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