Benzyne is an example of an aryne (-yne = triple bond) 
This is no ordinary triple bond as the second p interaction results from a weak interaction of sp² hybrid orbitals lying in the plane of the ring. 
The triple bond is non-linear due to the constraints of the 6-membered ring. 
Benzyne is strained and highly reactive and tends to undergo addition reactions.

 

 

 

Benzyne synthesis:

 

 

 

This mechanism requires a strong base is present (for example NaNH₂, BuLi) and is commonly used with haloaromatic substrates.