Question:medium

The compound $C_7H_8$ undergoes the following reactions: $ { C_7H_8 ->[3 \, Cl_2 / \Delta] A ->[Br_2 /Fe] B ->[Zn / HCl ] C }$ The product ??$C$ ' is

Updated On: May 7, 2026
  • p-bromotoluene
  • m-bromotoluene
  • 3-bromo-2,4,6-trichlorotoluene
  • o-bromotoluene
Show Solution

The Correct Option is B

Solution and Explanation

To solve the given problem involving the reactions of the compound $C_7H_8$ (toluene), we need to analyze the sequence of reactions step-by-step:

  1. The compound $C_7H_8$ is toluene. When toluene is treated with chlorine in the presence of heat (denoted by $\Delta$), it results in a substitution reaction. Specifically, the methyl group in toluene is substituted to form benzyl chloride derivatives. Here, $3 \, Cl_2/\Delta$ suggests multiple substitutions can occur, resulting in trichlorotoluene, with chlorine replacing hydrogen atoms in the methyl group.

  2. The product from the first step is reacted with bromine ($Br_2$) in the presence of iron (Fe). This reaction typically involves electrophilic aromatic substitution, where one of the hydrogens on the phenyl ring is replaced by a bromine atom. The presence of chlorine atoms (from the first step) deactivates ortho- and para- positions due to steric and electronic effects, promoting substitution at the meta position.

  3. Finally, the compound is treated with zinc in hydrochloric acid ($Zn/HCl$), which is a reduction reaction. This step reduces any excessive electrophilic character on the chlorinated methyl group, possibly restoring some hydrogen, but primarily it will not change the positioning of the bromine on the benzene ring.

Taking into account these transformations, we derive the following:

  • Step 1 results in 2,4,6-trichlorotoluene.
  • Step 2 results in bromination at the meta position relative to the methyl group due to deactivation of ortho/para positions by chlorine.
  • Step 3 mainly restores or stabilizes the system as m-bromotoluene.

Thus, the final product after completing these reactions is meta-bromotoluene (m-bromotoluene), making the correct answer:

  • m-bromotoluene
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