Question

Benzyl chloride $\left(C_6{H}_{5}C{H}_{2}Cl\right)$ can be prepared from toluene by chlorination with?
A. $S{O}_{2}C{l}_2$
B. $SOC{l}_2$
C. $C{l}_2$
D. NaOCI

Answer 1

Hint: Benzyl chloride$\left(C_6{H}_{5}C{H}_{2}Cl\right)$ can be prepared from toluene by chlorination with $C{l}_2$. This is because it is found that in the presence of sunlight, $C{l}_2$ gives free radicals. This reaction is basically a free radical substitution reaction.

Complete answer:
- We can see that in toluene there is no electrophilic centre, hence oxidation takes place in the presence of sunlight using $C{l}_2$.
- $S{O}_{2}C{l}_2$ is found to give chlorination, when there is a nucleophilic substitution reaction on an electrophilic centre. But as we know, there is no electrophilic centre in toluene, therefore, chlorination occurs by a controlled free radical mechanism.
- NaOCI Is found to give substitution reaction, and doesn’t give free radical so it will take part in chlorination.
- We can see the chlorination reaction that is, toluene by chlorination with $C{l}_2$ will give Benzyl chloride as:

- Benzyl chloride is used in large scale in making resins, dyes, lubricants, drugs and cosmetics.

- Hence, we can conclude that the correct option is (c), that is Benzyl chloride$\left(C_6{H}_{5}C{H}_{2}Cl\right)$ can be prepared from toluene by chlorination with $C{l}_2$.

Note: - Industrially, Benzyl chloride can be prepared from toluene and chlorine by the gas phase photochemical mechanism. During this reaction HCl is obtained as a side product.
- It is also found that Benzyl chloride has a strong smell, inflammable to skin and can cause tearing of eyes.