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Electron Density of Aromatic Rings - Effect of Methyl Groups

Tetracyanoethylene in dichloromethane is added to benzene, toluene, m-xylene, and mesitylene. The colors of the resulting products are compared.

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.5 MB, 9 seconds

File: MOVIES/TRAM08/0222806.MOV

Voiceover
The intensity of the colors of complexes between benzene derivatives and tetracyanoethylene reveals the electron density on the aromatic rings.

Discussion
A 1% solution of tetracyanoethylene (TCNE) in dichloromethane is added to four test tubes containing benzene, toluene, m-xylene, and mesitylene respectively. The intensity of the color of the resulting p-complex increases with increasing electron density on the aromatic ring. A methyl group is electron donating and its effect is additive with mesitylene showing the highest electron density.


       

Citation:  
  Kolb, K. E. J. Chem. Educ. 1989, 66, p 853.
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