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JEE Main2026Jan 23, Shift 1Chemistry
Q.

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

  1. A

    (i) NaOH (aq) (ii) Jones reagent (iii) HO

  2. B

    (i) BH/HO (ii) NaOEt (iii) Jones reagent

  3. C

    (i) Jones reagent (ii) NaOEt (iii) Hot KMnO/KOH

  4. D

    (i) NaOEt (ii) BH/HO (iii) Jones reagent

Solution

The chain has to be both moved from the benzylic carbon onto the next carbon and oxidised to —COOH. The sequence that does this cleanly:

Step 1 — NaOEt (E2): elimination of HBr from PhCH(Br)CH gives styrene PhCH=CH.

Step 2 — BH / HO (anti-Markovnikov hydration): styrene → PhCHCHOH (2-phenylethanol). The OH lands on the terminal carbon, moving the functional group away from the benzylic position.

Step 3 — Jones reagent (CrO / HSO): oxidation of the primary alcohol straight through to the carboxylic acid PhCHCOOH.

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