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Aldehydes Ketones and Carboxylic Acids question

2012 · Shift 0 · Q10
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Aldehydes Ketones and Carboxylic Acids question

2012 · Shift 0 · Q10

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
In the given transformation, which of the following is the most appropriate reagent ? AIEEE 2012 Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 223 English
  1. A
    NH2NH2,OHΘN{H_2}N{H_2},\mathop {OH}\limits^\ThetaNH2​NH2​,OHΘ
  2. B
    Zn−Hg/HClZn - Hg/HClZn−Hg/HCl
  3. C
    Na,Liq NH3Na,Liq\,N{H_3}Na,LiqNH3​
  4. D
    NaBH4NaB{H_4}NaBH4​
View written solutionFree

Correct answer: A

The reaction image is not visible in the prompt, so I must infer the intended transformation from the reagent options.

The options are standard reagents for different types of carbonyl reductions:

  1. Option A: NH2NH2,  OH−NH_2NH_2, \; OH^-NH2​NH2​,OH−

    • This is Wolff–Kishner reduction.
    • It converts aldehydes/ketones to hydrocarbons: R2C=O⟶R2CH2R_2C=O \longrightarrow R_2CH_2R2​C=O⟶R2​CH2​
    • It works in strongly basic medium.
  2. Option B: Zn−Hg/HClZn-Hg/HClZn−Hg/HCl

    • This is Clemmensen reduction.
    • It also converts aldehydes/ketones to hydrocarbons: R2C=O⟶R2CH2R_2C=O \longrightarrow R_2CH_2R2​C=O⟶R2​CH2​
    • It works in strongly acidic medium.
  3. Option C: Na, liq NH3Na,\,liq\ NH_3Na,liq NH3​

    • This is a dissolving metal reduction.
    • Commonly used for reduction of alkynes to trans-alkenes or Birch reduction of aromatic rings.
    • It is not the usual reagent for simple aldehyde/ketone to methylene conversion.
  4. Option D: NaBH4NaBH_4NaBH4​

    • This reduces aldehydes/ketones to alcohols, not hydrocarbons: RCHO→RCH2OH,RCOR′→RCH(OH)R′RCHO \to RCH_2OH, \qquad RCOR' \to RCH(OH)R'RCHO→RCH2​OH,RCOR′→RCH(OH)R′

Step-by-step reasoning

Step 1: Identify what kind of transformation these choices suggest

Among the options, A and B both perform deoxygenation of a carbonyl group to a methylene group.

So the intended reaction is most likely: >C=O⟶>CH2>C=O \longrightarrow >CH_2>C=O⟶>CH2​

Step 2: Distinguish between A and B

  • If the substrate is base-sensitive, Clemmensen is avoided and Wolff–Kishner is preferred.
  • If the substrate is acid-sensitive, Wolff–Kishner is preferred over Clemmensen.

In many JEE problems, when the answer is specifically A, it usually means the molecule likely contains an acid-sensitive group, so Wolff–Kishner reduction is the most appropriate reagent.

Step 3: Eliminate incorrect options

  • C does not generally carry out this transformation.
  • D gives alcohol, not complete reduction to hydrocarbon.
  • Between A and B, the stored answer indicates A, which is consistent with choosing Wolff–Kishner reduction as the more appropriate reagent.

Final answer

The most appropriate reagent is: A  :  NH2NH2,  OH−\boxed{A\; :\; NH_2NH_2,\; OH^-}A:NH2​NH2​,OH−​

This is the Wolff–Kishner reduction reagent.

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