Question

PROCEDURE

You will be provided with a mixture of two of the following four organic components dissolved in methyl tert-butyl ether. If present, they are present at the concentrations given below:

• benzoic acid, 0.200 M

• ethyl – 4 – aminobenzoate, 0.200 M

• naphthalene, 0.200 M

Your goals are: (1) to determine which of the above four molecules are present in the sample that was provided to you and (2) to isolate a sufficient quantity to determine a melting point and hand in a product. You will be provided with a worksheet that you will need to hand in with your products.

You will be given ~20 mL of the methyl tert-butyl ether solution. Be sure to write down your unknown letter and the exact amount of your sample.

The following solutions and materials will be available for you to use: 10% HCl, 6M HCl, 10% NaOH, 6M NaOH, saturated NaCl, litmus paper, and drying agent.

Write a flow chart for these reactions.

Answer 1

Step 1: Dissolve your sample in 20 mL of the methyl tert-butyl ether. Treat your solution with 10% HCl, decant the water layer and treat with 10% NaOH, solid is generated then your sample is having ethyl-4-aminobenzoate.

Step2: Treat the organic layer with 10% NaOH, decant the water layer and treat with 10% HCl, solid is generated, your sample is having benzoic acid.

Step 3: Evaporate the organic layer, if you got the solid then your sample is having naphthalene.