MCQMediumJEE 2025Electrophilic Substitution in Benzene

JEE Chemistry 2025 Question with Solution

Choose the correct set of reagents for the following conversion:

Reaction scheme showing ethyl benzene converted into a benzene ring bearing a vinyl group at one position and bromine at the para position.
  • A

    Cl2/Fe; Br2/anhy. AlCl3; aq. KOHCl_2/Fe;\ Br_2/anhy.\ AlCl_3;\ aq.\ KOH

  • B

    Br2/Fe; Cl2,Δ; alc. KOHBr_2/Fe;\ Cl_2,\Delta;\ alc.\ KOH

  • C

    Cl2/anhy. AlCl3; Br2/Fe; alc. KOHCl_2/anhy.\ AlCl_3;\ Br_2/Fe;\ alc.\ KOH

  • D

    Br2/anhy. AlCl3; Cl2,Δ; aq. KOHBr_2/anhy.\ AlCl_3;\ Cl_2,\Delta;\ aq.\ KOH

Answer

Correct answer:B

Step-by-step solution

Standard Method

Given: The conversion is from ethyl benzene to a product having Br on the benzenoid ring and a vinyl group CH=CH2CH=CH_2 on the side chain.

Find: The correct sequence of reagents.

From the solution, the correct option is stated as B.

The extracted working says:

  1. Bromination of ethyl benzene is carried out using Br2/FeBr_2/Fe.
  2. Then chlorination under heat, Cl2,ΔCl_2, \Delta, is used.
  3. Finally, alc. KOH causes elimination to generate the double bond.

Thus the reagent sequence is Br2/Fe; Cl2,Δ; alc. KOHBr_2/Fe;\ Cl_2,\Delta;\ alc.\ KOH

Therefore, the correct option is B.

Extracted Approach

Given: Ethyl benzene is converted to a brominated styrene derivative.

Find: Which listed reagent set matches the conversion.

The solution explains that bromination of ethylbenzene first occurs using Br2Br_2 in the presence of Fe. Then chlorination under heating, Cl2,ΔCl_2, \Delta, is used. After that, dehydrohalogenation with alc. KOH forms the required double bond.

So the sequence identified in the source solution is: Br2/Fe; Cl2,Δ; alc. KOHBr_2/Fe;\ Cl_2,\Delta;\ alc.\ KOH

This corresponds to option (2).

Hence, the correct option is B.

Common mistakes

  • Using aq. KOH instead of alc. KOH is incorrect because aqueous KOH generally favors substitution or hydrolysis, whereas alcoholic KOH is used for dehydrohalogenation to form the required double bond. Use alc. KOH for elimination.

  • Confusing ring bromination with side-chain halogenation leads to an incorrect sequence. The solution identifies the needed sequence as starting with Br2/FeBr_2/Fe and then proceeding to steps that ultimately generate the vinyl group. Follow the source-indicated reagent order rather than assuming any halogenation condition will work.

  • Selecting a chlorine-first option is incorrect because the extracted solution explicitly concludes that the valid sequence begins with Br2/FeBr_2/Fe. When a solution provides the final reagent order, match the sequence exactly with the options.

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