Question:

The reaction of toluene with $Cl_2$ in the presence of $FeCl_3$ gives 'X' and reaction in presence of light gives 'Y' Thus, 'X' and 'Y' are

Updated On: Jul 1, 2024
  • X = benzal chloride, Y = o-chlorotoluene
  • X = m-chlorotoluene, Y = p-chlorotoluene
  • X = o and p-chlorotoluene, Y = trichloromethyl benzene
  • X = benzyl chloride, Y = m-chlorotoluene
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The Correct Option is C

Solution and Explanation

In the presence of halogen carrier, electrophilic substitution occurs while in the presence of sunlight, substitution occurs at the side chain.
$FeCl_3+Cl_2 \longrightarrow$ $FeCl_4 ^- + Cl^+$
Electrophile attacking species ($ \because -CH_3 $ is an o/p-directing group.) .
In presence of $hv$ reaction is free radical.
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Concepts Used:

Preparation of Haloarenes

  1. Preparation by Electrophilic Substitution Reaction: Electrophilic Substitution helps in the preparation of Haloarenes like aryl bromides and aryl chlorides by using the halogens such as chlorine and bromine in the presence of Lewis Acid. But for this reaction to be fruitful, it is compulsory that the reaction takes place in the presence of Lewis Acid and must be carried out in dark.
  2. Preparation by Sandmeyer’s Reaction: In this case, in order to form diazonium salt in the presence of cold mineral water, the primary aromatic amine has to react with sodium nitrate. Here, the reaction of sodium nitrate with HX will prepare HNO2 at a temperature of 273-278 K.

Read More: Haloalkanes and Haloarenes