A mixture of aspirin, aniline and toluene was dissolved in 35 mL of dichlorometh
ID: 503160 • Letter: A
Question
A mixture of aspirin, aniline and toluene was dissolved in 35 mL of dichloromethane and placed into a separatory funnel. Next, 35 mL of aqueous HCI was added to the separatory funnel. The funnel was inverted a. Which solvent is the top layer? b. Which layer (specify aq. or org.) contains the aspirin? c. Which layer (specify aq. or org.) contains the toluene? d. Identify the substance (if any) that is extracted into the aqueous layer. e. Write an equation to illustrate any compound that is converted into a water-soluble species.Explanation / Answer
Aspirin is slightly soluble in cold water and dissloves fast in hot water.
Toulene is a neutral substance and it is soluble in the organic solvent dichloromethane and insoluble in water.
HCl(aq) will react with aniline to form anilinium chloride, C6H7NH+Cl-, which is water-soluble. The anilinium salt will go to the aqueous phase.Hence aniline dissolves in dil.HCl.
a) Toulene will be in the top layer as it is less denser than aqueous layers.
b) Aqueous layer contains the aspirin.
c) Organic layer contains toulene.
d) It is aniline. HCl(aq) will react with aniline to form anilinium chloride, C6H7NH+Cl-, which is water-soluble. The anilinium salt will go to the aqueous phase.Hence aniline dissolves in dil.HCl.
e) HCl(aq) will react with aniline to form anilinium chloride, C6H7NH+Cl-, which is water-soluble.
C6H5 NH2 + HCl(aq) ------------> C6H5NH3+Cl-(aq)
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