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Extraction of Dichloroindophenol

Dichloroindophenol is extracted demonstrating "like dissolves like".

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3.5 MB, 56 seconds

File: MOVIES/TRAM13/0423318.MOV

Voiceover
A few drops of hydrochloric acid are added to a separatory funnel containing an aqueous solution of the blue sodium salt of 2,6-dichloroindophenol and toluene. The less dense toluene is the top layer. The funnel is shaken and vented. The aqueous layer becomes clear and the toluene layer is red. A few drops of sodium hydroxide are then added. The blue 2,6-dichlorophenoxide anion is polar and water soluble. Red 2,6-dichlorophenol is nonpolar and soluble in the nonpolar solvent toluene. After shaking, the mixture is restored to its original state.

Discussion
An aqueous solution of the blue sodium salt of 2,6-dichloroindophenol is placed in a separatory funnel containing toluene. The less dense toluene is the top layer. A few drops of 2M HCl are added and the funnel shaken. The aqueous layer becomes clear and the toluene becomes red. A few drops of sodium hydroxide are then added and, after shaking, the mixture is restored to its original state. The blue 2,6-dichlorophenoxide anion is polar and water soluble. Red 2,6-dichlorophenol is nonpolar and soluble in the nonpolar solvent toluene. This is an example of the general rule for solubility - "like dissolves like".


       

Citation:  
  Silversmith, E. F. J. Chem. Educ. 1972, 49, p A694.
Design, Text and Demonstrator:  
  Gary Trammell University of Illinois at Springfield, Springfield, IL 62794
Videographer/Editor:  
  Steve Dykema University of Illinois at Springfield, Springfield, IL 62794
Voice:  
  Margaret Biddle University of Wisconsin - Madison, Madison, WI 53706
Audio Production:  
  Greg Minix University of Wisconsin - Madison, College of Engineering, Madison, WI 53706
  Jerrold J. Jacobsen University of Wisconsin - Madison, Madison, WI 53706