Toluene is subjected to two different sets of reaction conditions as follows: Reaction 1: Toluene reacts with Cl ₂ in the presence of FeCl ₃ in the dark to give P as the major product. Reaction 2: Toluene reacts with excess Cl ₂ in the presence of sunlight to give Q , which upon hydrolysis with water at 373 K yields R . Identify the products P and R respectively.

Step-by-step solution

In Reaction 1, the reaction of toluene with Cl ₂ in the presence of a Lewis acid ( FeCl ₃ ) in the dark proceeds via electrophilic aromatic substitution. The methyl group is an ortho/para directing group. Due to steric hindrance at the ortho position, the major product P is p -chlorotoluene. In Reaction 2, the reaction of toluene with excess Cl ₂ in the presence of sunlight proceeds via free radical substitution at the benzylic position. The use of excess chlorine leads to exhaustive chlorination, forming benzotric