Question

Draw the products of each reaction.

Short answer

Phenol is an ortho-para directing group due to the maximum electron density at ortho and para positions. In the presence of Lewis acid, a trichloro compound is formed.

Step-by-step solution

Phenol

Phenol is an ortho-para directing group due to the maximum electron density at ortho and para positions. In the presence of Lewis acid, a trichloro compound is formed.

OH as ortho-para directing group

The OH group has a lone pair of electrons which it donates to the benzene ring to create maximum electron density. The delocalization of electrons is maximum at ortho and para positions.

Explanation

a. The chlorination of phenol in the presence of Lewis acid gives trichlorophenol, as shown below.

b. The substituent on the benzene ring is OH which is electron-donating. The chlorination of phenol gives ortho and para chlorophenol due to the maximum electron density at these positions.

c. Toluene is also an electron-rich compound, but the methyl group is a sigma donor. It donates its electrons to the ring slower than the OH group in phenol.

Therefore, in the presence of Lewis acid, ortho and para products are formed.