MCQMediumJEE 2026Alkyl Halides

JEE Chemistry 2026 Question with Solution

Reaction conversion showing compound X as brominated side-chain benzene derivative converting to compound Y as phenylpropionic acid, with a question mark over the reaction arrow.

The correct sequence of reagents for the above conversion of X to Y is :

  • A

    (i) NaOH (aq)\text{(aq)} (ii) Jones reagent (iii) H3O+H_3O^+

  • B

    (i) NaOEt (ii) B2H6/H2O2B_2H_6/H_2O_2 (iii) Jones reagent

  • C

    (i) B2H6/H2O2B_2H_6/H_2O_2 (ii) NaOEt (iii) Jones reagent

  • D

    (i) Jones reagent (ii) NaOEt (iii) Hot KMnO4/KOHKMnO_4/KOH

Answer

Correct answer:B

Step-by-step solution

Standard Method

Given: Conversion of X to Y is shown.

Find: The correct sequence of reagents.

The solution states that the required strategy is to first form an alkene, then carry out anti-Markovnikov hydration, and finally oxidize the resulting primary alcohol.

  1. NaOEt causes dehydrohalogenation of the alkyl halide to give an alkene.
  2. B2H6/H2O2B_2H_6/H_2O_2 performs hydroboration-oxidation, giving the anti-Markovnikov alcohol.
  3. Jones reagent then oxidizes the primary alcohol to the carboxylic acid.

The hint also states that Jones reagent (CrO3/H2SO4)\left(CrO_3/H_2SO_4\right) is a strong oxidant that converts a primary alcohol into a carboxylic acid.

Therefore, the correct option is B.

Stepwise Functional Group Transformation

Given: X is an alkyl halide attached to a benzene side chain, and Y is the corresponding side-chain carboxylic acid.

Find: Which reagent sequence achieves this transformation.

Identify principle: The product requires oxidation at the terminal carbon, so an intermediate primary alcohol is needed before final oxidation.

Apply the sequence shown in the solution:

  • Step 1: NaOEt performs elimination to form an alkene.
  • Step 2: B2H6/H2O2B_2H_6/H_2O_2 gives anti-Markovnikov addition, producing a primary alcohol.
  • Step 3: Jones reagent oxidizes that primary alcohol completely to the carboxylic acid.

Hence the sequence is (i) NaOEt (ii) B2H6/H2O2B_2H_6/H_2O_2 (iii) Jones reagent.

Therefore, the correct option is B.

Common mistakes

  • Choosing Jones reagent in the first step is incorrect because it is an oxidizing agent, not a reagent for dehydrohalogenation. First form the alkene using NaOEt, then proceed further.

  • Using B2H6/H2O2B_2H_6/H_2O_2 before alkene formation is incorrect because hydroboration-oxidation requires an alkene substrate. The elimination step must occur first.

  • Assuming the oxidation stops at an aldehyde is incorrect here. Jones reagent is a strong oxidant and takes a primary alcohol to the carboxylic acid.

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