Benzyne mechanism

Benzyne mechanism

Jul 25, 2022, 16:45 IST

About Benzyne mechanism

Benzyne is very different from what can be expected from simple concepts of chemical bonding. All six carbon atoms are sp2 hybridized. Three normal π bonds are formed by p orbitals of each carbon. These π bonds are completely delocalized in the benzene ring. However, sp2 hybrid orbitals of two carbon atoms overlap in sideways manner to form a special π bond. This special π bond is very weak because the sp2 hybrid orbitals were directed slightly away and the extent of overlapping is very poor. The presence of six completely delocalized π electrons makes benzyne aromatic . On the other hand, presence of a very weak π bond makes it highly unstable (it cannot be isolated and acts as intermediate only).Revise organic from chemistry formulas page.

Behaviour of Benzyne:

Inspite of high π electron density, benzyne does not react with electrophile because it will generate a cation having sp hybrid atom in six membered ring ( not generated due to very large strain).In spite of high π electron density, benzyne can react with nucleophile because it will generate sp2 hybrid carbanion that is stable.In absence of nucleophile, benzyne can undergo dimerization although it will generate anti aromatic ring.

Find Below the detail reaction Mechanism of Benzyne