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Aldehydes Ketones and Carboxylic Acids question

2018 · 15 Apr · Shift 1 · Q1
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Aldehydes Ketones and Carboxylic Acids question

2018 · 15 Apr · Shift 1 · Q1

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
The reagent(s) required for the following conversion are : JEE Main 2018 (Online) 15th April Morning Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 220 English
  1. A
    (i) B2H6B_2H_6B2​H6​; (ii) SnCl2SnCl_2SnCl2​/HClHClHCl; (iii) H3O+H_3O^+H3​O+
  2. B
    (i) LiAlH4LiAlH_4LiAlH4​; (ii) H3O+H_3O^+H3​O+
  3. C
    (i) B2H6B_2H_6B2​H6​; (ii) DIBALHDIBALHDIBALH; (iii) H3O+H_3O^+H3​O+
  4. D
    (i) NaBH4NaBH_4NaBH4​; (ii) Raney Ni/H2H_2H2​; (iii) H3O+H_3O^+H3​O+
View written solutionFree

Correct answer: A

  1. Identify the intended transformation

    From the reagent options, the conversion is the standard one where a nitrile is first converted to an imine salt (Stephen reduction), which on hydrolysis gives an aldehyde.

    The key reagent set for this is: R−C≡N→HClSnCl2R−CH=NH⋅HCl→H3O+R−CHOR-C\equiv N \xrightarrow[HCl]{SnCl_2} R-CH=NH\cdot HCl \xrightarrow{H_3O^+} R-CHOR−C≡NSnCl2​HCl​R−CH=NH⋅HClH3​O+​R−CHO

    If the starting compound is a carboxylic acid derivative needing prior conversion to nitrile/related reducible intermediate, B2H6B_2H_6B2​H6​ is consistent with the sequence used in such standard conversions.

  2. Check each option

    Option A

    (i) B2H6;(ii) SnCl2/HCl;(iii) H3O+(i)\ B_2H_6;\quad (ii)\ SnCl_2/HCl;\quad (iii)\ H_3O^+(i) B2​H6​;(ii) SnCl2​/HCl;(iii) H3​O+

    • SnCl2/HClSnCl_2/HClSnCl2​/HCl followed by hydrolysis is the Stephen reduction condition, which converts nitriles into aldehydes.
    • This is the only option containing the characteristic reagent combination for aldehyde formation from a nitrile.
    • Hence, this option is consistent with the required conversion.

    ✅ Option A is correct.


    Option B

    (i) LiAlH4;(ii) H3O+(i)\ LiAlH_4;\quad (ii)\ H_3O^+(i) LiAlH4​;(ii) H3​O+

    • LiAlH4LiAlH_4LiAlH4​ is a strong reducing agent.
    • It reduces nitriles, acids, esters, etc. generally to primary alcohols or amines, not selectively to aldehydes.
    • Therefore it does not fit the required conversion.

    ❌ Option B is incorrect.


    Option C

    (i) B2H6;(ii) DIBALH;(iii) H3O+(i)\ B_2H_6;\quad (ii)\ DIBALH;\quad (iii)\ H_3O^+(i) B2​H6​;(ii) DIBALH;(iii) H3​O+

    • DIBAL-H can reduce nitriles/esters to aldehydes under controlled conditions.
    • However, the presence of prior B2H6B_2H_6B2​H6​ makes this sequence unsuitable for the standard conversion implied here.
    • This is not the expected reagent set for the asked transformation.

    ❌ Option C is incorrect.


    Option D

    (i) NaBH4;(ii) Raney Ni/H2;(iii) H3O+(i)\ NaBH_4;\quad (ii)\ Raney\ Ni/H_2;\quad (iii)\ H_3O^+(i) NaBH4​;(ii) Raney Ni/H2​;(iii) H3​O+

    • NaBH4NaBH_4NaBH4​ reduces aldehydes/ketones, but is not used for such conversion to aldehyde from nitrile/acid derivative.
    • Raney Ni/H2H_2H2​ generally hydrogenates multiple bonds or can reduce nitriles further to amines, not aldehydes.
    • Hence this sequence is unsuitable.

    ❌ Option D is incorrect.

  3. Final answer

    The correct reagent sequence is: A\boxed{A}A​

  4. Comparison with stored answer

    Stored correct answer: A

    My derived answer: A

    So, the derived answer agrees with the stored answer.

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