Question

Provide a flow chart detailing the acid/base extraction/separation of the compounds show below. Your answer must employ the following reagents: methylene chloride, hydrochloric acid (1M & 6M), sodium hydroxide (1M & 6M), 10% sodium bicarbonate (aq). Clearly indicate the product(s) and layers formed following each step of your separation scheme. IMPORTANT: p-cresol is soluble in sodium hydroxide solution but insoluble in neutral water or sodium bicarbonate solution. 2-ethylbenzoic acid is soluble in both sodium hydroxide and sodium bicarbonate solutions. Use skeletal structures only in your answer: Why must you remove the separatory funnel stopper prior to opening the stopcock and draining out the lower layer? 3.During your extraction, you become confused as to which layer is the organic and which is the aqueous. How would you identify them experimentally? 4.Why is the solubility of a neutral organic compound unaltered by exposure to aqueous acid or base? 5.Identify which of the following solvents in each pair would constitute the "upper" layer in a liquid/liquid extraction solution. If layer separation would not be observed, indicate this by stating "miscible." Ethyl acetate and 6M sodium hydroxide solution (aq): Diethyl ether and water: 6.Acetone is an organic solvent in which all three components of the 3-component mixture are soluble. Why would it not be a good substitute for dichloromethane in this experiment?

Answer 1

2. We must remove the stopper of separating funnel first. separating funnel will be having high pressure than normal because vigrous shaking as well if you NaHCO3 there will CO2. It must be removed before opening stopper.

3. If u keep down a drop of organic layer it will be evaporated with in a minute. But not aqueous layer.

4. functional groups in organic molecule will be neutral and soluble in organic solvents only untill it exposed acid or base. after treating with acid or base it wil become salt which is soluble in aqueous.

5. Based on density layer will be either down or top.

ethyl acetate have lesser dense than water hence it will upper layer with 6M NaOH

Diethyl ether also have lesser dense than water hence it will upper layer with water

6. Acetone is miscible with water as well as organic solvents. we can not separete the layer till acetone presents with compounds.