Question

SEPARATION, PURIFICATION AND IDENTIFICATION OF TWO UNKNOWNS IN A MIXTURE

You will be given a mixture containing two unknowns, each containing one or more functional groups:

- one is a solid carboxylic acid

- one is a liquid that is not a carboxylic acid - boiling point is between 95 and about 200˚C

Your goals are to:

- separate the two compounds, getting the best recovery you can of each (you will be asked to report percent recovery)

- purify each of the two compounds

- identify the two compounds

Minimum required properties of the compounds to be determined:

For the solid carboxylic acid:

- melting point

- 1H NMR spectrum (but NOT 13C NMR)

- IR spectrum run as a KBr pellet

- TLC to assess purity

For the liquid:

- boiling point

- 1H NMR spectrum

- 13C NMR spectrum

- IR spectrum

- GC to assess purity

1. Both unknowns are generally soluble in the organic solvent methyl tert-butyl ether (MTBE) and not very soluble in water. 5% NaOH will be available in case you think of a good use for it in the separation.

2. Various recrystallization and NMR solvents will be available.

Need help for the detailed flowchart showing how you can plan to separate and AND purify the two components in your unknown mixture.