Benzyne, C6H4, is a highly energetic and reactive molecule. What hybridization do you expect for the two triply bonded carbon atoms? What are the 'theoretical' values for the C¬C‚C bond angles? Why do you suppose benzyne is so reactive?

Key Concepts

Hybridization

Hybridization is the concept of mixing atomic orbitals to form new hybrid orbitals that can accommodate the bonding requirements of a molecule. In the case of benzyne, the two triply bonded carbon atoms are expected to exhibit sp hybridization, which involves the mixing of one s orbital and one p orbital, resulting in two sp hybrid orbitals that are oriented linearly.

Bond Angles

Theoretical bond angles are determined by the hybridization of the atoms involved. For sp hybridized carbon atoms, the ideal bond angle is 180 degrees, as the hybrid orbitals are arranged linearly. In benzyne, the presence of the triple bond influences the geometry, leading to bond angles that may deviate slightly from the ideal due to steric and electronic effects.

Reactivity of Benzyne

Benzyne is highly reactive due to the presence of a triple bond between two carbon atoms, which creates significant electron density and strain in the molecule. This reactivity is further enhanced by the instability of the benzyne structure, making it prone to undergo various chemical reactions, such as nucleophilic attacks, to relieve the strain and achieve a more stable configuration.