Roberts et al. carried out an important experiment to prove the existence of benzine. Chlorobenzene labeled with ¹⁴C at the position to which the chlorine was attached was treated with sodium amide in liquid ammonia and the aniline formed was analyzed for the ¹⁴C position. The results are indicated in the figure. Show how these data are consistent with the benzyne intermediate.

 

 

 

Halogenated benzenes lacking ortho/para deactivating groups react with nucleophiles via the nucleophilic aromatic substitution (elimination-addition) mechanism. This reaction occurs through an intermediate called benzyne.