JEE Main · 2025 · Shift-IIeasyHC-071

Identify product [A], [B] and [C] in the following reaction sequence:

Hydrocarbons · Class 11 · JEE Main Previous Year Question

Question

Identify product [A][A], [B][B] and [C][C] in the following reaction sequence: image

Options
  1. a

    [A]:\ceCH3CH2CH3[A]: \ce{CH3CH2CH3}; [B]:\ceCH3CHO[B]: \ce{CH3CHO}; [C]:\ceHCHO[C]: \ce{HCHO}

  2. b

    [A]:\ceCH2=CH2[A]: \ce{CH2=CH2}; [B]:\ceH3CCOCH3[B]: \ce{H3C-CO-CH3}; [C]:\ceHCHO[C]: \ce{HCHO}

  3. c

    [A]:\ceCH3CH=CH2[A]: \ce{CH3CH=CH2}; [B]:\ceCH3CHO[B]: \ce{CH3CHO}; [C]:\ceCH3CH2OH[C]: \ce{CH3CH2OH}

  4. d

    [A]:\ceCH3CH=CH2[A]: \ce{CH3CH=CH2}; [B]:\ceCH3CHO[B]: \ce{CH3CHO}; [C]:\ceHCHO[C]: \ce{HCHO}

Correct Answerd

[A]:\ceCH3CH=CH2[A]: \ce{CH3CH=CH2}; [B]:\ceCH3CHO[B]: \ce{CH3CHO}; [C]:\ceHCHO[C]: \ce{HCHO}

Detailed Solution

Step 1: Pd/C + H2_2 (Lindlar-type) -- partial hydrogenation

Propyne \ceCH3CCH\ce{CH3-C≡CH} + 1 mol \ceH2\ce{H2} with \cePd/C\ce{Pd/C} \rightarrow propene \ceCH3CH=CH2\ce{CH3-CH=CH2} (syn addition, cis alkene from internal alkynes; terminal gives propene directly).

[A]=\ceCH3CH=CH2[A] = \ce{CH3-CH=CH2}

Step 2: Ozonolysis with reductive workup (Zn/H2_2O) image Key Points:

  • \cePd/C\ce{Pd/C} + \ceH2\ce{H2}: reduces alkyne \rightarrow alkene (1 mol \ceH2\ce{H2})
  • Reductive ozonolysis: \ceRCH=\ce{RCH=} \rightarrow \ceRCHO\ce{RCHO}; \ce=CH2\ce{=CH2} \rightarrow \ceHCHO\ce{HCHO}
  • Oxidative workup (\ceH2O2\ce{H2O2}) would give \ceRCOOH\ce{RCOOH} instead

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Identify product [A], [B] and [C] in the following reaction sequence: (JEE Main 2025) | Canvas Classes