Question

Draw all products formed when m-chlorotoluene is treated with ${\text{KNH}}_{\text{2}}$in${\text{NH}}_{\text{3}}$

Short answer

Three possible products:

Step-by-step solution

Potassium amide

Potassium amide $\left({\text{KNH}}_{\text{2}}\right)$ is an inorganic reagent used as a strong base in the nucleophilic substitution of an aromatic ring.

Treatment of aryl halides with a strong base like $\left({\text{KNH}}_{\text{2}}\right)$in the presence of ${\text{NH}}_{\text{3}}$ produces the reactive intermediate, benzyne.

Reaction of aryl halide and potassium amide

The reaction of m-chlorotoluene with ${\text{KNH}}_{\text{2}}$ in the presence of ${\text{NH}}_{\text{3}}$ produces two possible benzyne reactive intermediates.

Benzyne upon further treatment with ${\text{KNH}}_{\text{2}}$in the presence of ${\text{NH}}_{\text{3}}$, produces three possible products.