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 N,N-diethyl-3-methylbenzamide from m-toluic acid and the reaction did not go to completion and the student ended up with a mixture of both compounds. Purify the m-toluic 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

1: Preparation of N,N-diethyl-m-toluamide

Slowly add the diethylamine hydrochloride to the aqueous NaOH, with swirling. Once all the diethylamine hydrochloride has been added, and dissolved, add all of the sodium lauryl sulfate.

Transfer the m-toluyl chloride prepared in the first reaction to a separatory funnel, which will be used for dropwise addition of the acyl chlorde to the flask. After each drop or two, swirl the flask to mix its contents. Once the addition is complete, continue swirling the flask for another 5 minutes to ensure complete mixing of reactants and cover the flask also.

2: Purification and Analysis of N,N-diethyl-m-toluamide

Extract the reaction mixture in a Separatory Funnel using two 25-mL portions of ether1. T

hree phases in the Separatory Funnel:

Pour the lower phase liquid back into the Separatory Funnel, add your second 25-mL portion of ether and repeat the extraction, collecting only the upper ether phase.

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