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 2-methoxynaphthalene from 2- napthol via an SN2 reaction with methyl iodide and the reaction did not go to completion and the student ended up with mainly the starting material and some product. Recover the 2-napthol so you can reuse it again. Provide data to show that your 2-napthol is purified and recovered.

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

In a mixture of starting material 2-naphthol and 2-methoxynephthalene we add dichlormethane. 2-naphthol is an alcohol like phenol so it would react with 1 M NaOH when added and forms a sodium salt. The salt goes in water layer. Dichlormethane is heavier (denser) than water and would be the lower layer. Separate the water layer and acidify with 1 M HCl to reprecipitate 2-naphthol from the solution.

If you run a TLC, the ether methoxynaphthalene would have higher Rf value than 2-naphthol, the developing solvent would be 10% ethylacetate in 90% hexane.

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