1. para-toluide, mp 45 degrees Celcius, is very soluble in ehter but only slightly soluble in water. it is an organic base which reacts with aqueous hydrochloric acid to form a water-soluble salt which is insoluble in ether.

CH3-C6H4-NH2 + H+ + Cl- ------> CH3-C6H4-NH3+ + Cl-

Given a mixture of para-toluifine and fluorenone, devise a procedure based upon solent-solvent extraction to seperate these compounds. Give you answer in the form of a flow chart.

2. Suppose we extract an aqueous solution which is very dense (because it contains heavy salts) with methylene chloride and, when the layers separate, we are not sure which is the aqueous layer and which is the methylene chloride layer. What simple experimental procedure could be used to settle this problem?

3. (a) A 5.00-g sample of compound A was dissolved in 50 ml of water. This solution was then shaken with 50 ml of ether. At this point the ether was found to contain 2.00 g of compound A. Calculate the partition ratio: [A]ether / [A]water= alpha

(b) The aqueous solution was then extracted four more times with 50-mL portions of ether (a total of 5 extractions). How much of the compund remained in the aqueous layer? How much of compound A was in the five combined ether layers? What percentage of A was extracted from the water?

(c) How much A would have been extracted into ether if the orginal aqueous solution had been extracted once with a 500-mL portion of ether? What percentage of A would have been extracted by the ether?

4. Why is it necessary to wash the benzoic acid thoroughly with water; i.e., what is being removed?