JCE Software Chemistry Comes Alive!
Chlorination of Methyl Benzenes

Benzene, toluene, m-xylene, and mesitylene are added to a solution of chlorine in dichloromethane and the rates of reaction are compared.

  Click a thumbnail picture below to view a larger version. View movie.
View Movie
 

Narrative
Four test tubes contain a solution of chlorine in dichloromethane. Benzene, toluene, m-xylene, and mesitylene are added to the chlorine solution. Mesitylene reacts immediately and vigorously. m-Xylene reacts second. Benzene and toluene do not react under these conditions.

Discussion
The order of reactivity parallels the p-electron density shown in the previous section (Electron Density of Aromatic Rings - Effect of Methyl Groups).