2-Hexyne gives trans-2-hexene on treatment with

The attack of an odd electron from lithium takes place at more substituted carbon. The formed radical undergoes cis- trans isomerisation in order to prevent steric repulsions between lone pair- lone pair electrons. That’s why trans-hexene is the desired product in this case. The supply of proton takes place through the ammonia solution in reaction media. OH CH3 H2SO4 OH2 Methyl Shift HYDROCARBONS 9