JEE Main 2024 · 30 January · morning · Single correct · +4 / −1

This reduction reaction is known as:

JEE Main PYQ figure
  1. (a) Wolff-Kishner reduction
  2. (b) Etard reduction
  3. (c) Stephen reduction
  4. (d) Rosenmund reduction
Answer and solution

Answer (d) Rosenmund reduction

Solution

Chemistry ma’am · 3 steps

Acid chloride in, aldehyde out, with H₂ on poisoned palladium: that combination is Rosenmund.

  1. Read the reaction. Benzoyl chloride, C₆H₅COCl, becomes benzaldehyde, C₆H₅CHO. The C-Cl bond is replaced by C-H, and the C=O stays.

    C₆H₅COCl + H₂ →(Pd-BaSO₄) C₆H₅CHO + HCl

  2. Why poison the catalyst. BaSO₄ partly deactivates the palladium. The catalyst is then strong enough to break the C-Cl bond but too weak to reduce the aldehyde further to an alcohol, so the reaction stops at CHO.
    ReactionStarting materialReagentProduct
    Wolff-Kishneraldehyde or ketoneNH₂NH₂, then KOH, heatalkane (C=O → CH₂)
    EtardtolueneCrO₂Cl₂, then H₃O⁺benzaldehyde (an oxidation)
    StephennitrileSnCl₂ + HCl, then H₃O⁺aldehyde
    Rosenmundacid chlorideH₂, Pd-BaSO₄aldehyde
  3. So. Only Rosenmund matches an acid chloride reduced by H₂ over Pd-BaSO₄. The answer is (d).

The idea to keep. To name a reaction, match the starting material with the reagent. Acid chloride with H₂/Pd-BaSO₄ is Rosenmund. Nitrile with SnCl₂/HCl is Stephen. Toluene with CrO₂Cl₂ is Etard.

Answer from the NTA final answer key. Solution by PrepWiser.

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Asked about 130 times in JEE Main since 2020. This question is from 2024.