Question

The reaction of toluene with chlorine in presence of ferric chloride gives predominantly ________

• A. Benzoyl chloride
• B. m-chlorotoluene
• C. benzene
• D. o and p-chlorotoluene

Answer 1

The correct option is D o and p-chlorotoluene

In presence of $FeC{l}_3$ and in dark, electrophilic substitution on benzene ring by $C{l}^{+}$ ion at ortho and para positions occurs to give o and p-chlorotoluene.
This is because $-C{H}_3$ group increases the electron density at ortho and para positions due to Hyperconjugation $\left(H\right)$ effect as shown. So the electrophile $C{l}^{+}$ will readily attack ortho and para positions as compared to meta position :



Hence the correct option is D.