Question

On treatment with chlorine in presence of sunlight, toluene gives:
A. $o - chloro{\text{ }}toluene$
B. $2,5 - dichloro{\text{ }}toluene$
C. $p - chloro{\text{ }}toluene$
D. $benzyl{\text{ }}chloride$

Answer 1

Hint:Toluene which is one of the aromatic hydrocarbons is reacted with chlorine in the presence of sunlight and since toluene is a closed cyclic structure of benzene ring with a methyl group on one of its carbon hence, a substitution reaction will take place on an alkyl group of toluene. "Arenes" and "aryl-hydrocarbons" are also used to describe hydrocarbons such as toluene and phenol.

Complete step-by-step answer:
We know that Toluene is an aromatic compound having a methyl group on the benzene ring known as methylbenzene as shown in the following figure.
Now, this reaction involves the replacement of one hydrogen atom from the methyl group in methylbenzene with a chlorine atom.
On treating toluene $\left( {{C_6}{H_6} - C{H_3}} \right)$ with chlorine $C{l_2}$ in the presence of sunlight, the product will be benzyl chloride as shown below: -


Image:Formation of Benzyl chloride
In the given reaction, when toluene is treated with chlorine in presence of sunlight, $H$ atom of the methyl group in toluene is replaced with $Cl$ atom.
Thus, on treatment with chlorine in presence of sunlight, toluene gives Benzyl chloride.

Option ‘D’ is correct

Note: The creation of benzyl chloride arises from the reaction between methyl benzene and chlorine in the presence of sunlight in this problem, which is based on aromatic hydrocarbons. The process, however, can continue and lead to the creation of benzo-trichloride by having all three hydrogen atoms in the methyl group replaced by chlorine atoms.