JEE Challenger
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Calculate Mass of Product U in Organic Reaction Pathway

Comprehension Passage

In the reaction scheme given below, the percentage yields are indicated alongside each transformation step:

Here, x g\mathbf{x}\text{ g} and y g\mathbf{y}\text{ g} represent the masses of R\mathbf{R} and U\mathbf{U} obtained, respectively. (Take molar masses in g mol−1\text{g mol}^{-1}: H=1\text{H} = 1, C=12\text{C} = 12, and O=16\text{O} = 16)

Determine the value of y\mathbf{y}.

Question Diagram 1
Official Numerical Answer3.2

Step-by-Step Solution

To find the mass of product U\mathbf{U} (y gy\text{ g}), we analyze the step-by-step chemical transformations starting from P\mathbf{P}:

  1. Identification of Compound P\mathbf{P} and its Amount:

    • Mg2C3\text{Mg}_2\text{C}_3 undergoes hydrolysis to yield propyne (P\mathbf{P}): Mg2C3+4H2O→2Mg(OH)2+CH3−C≡CH\text{Mg}_2\text{C}_3 + 4\text{H}_2\text{O} \rightarrow 2\text{Mg(OH)}_2 + \text{CH}_3-\text{C}\equiv\text{CH}
    • Molar mass of propyne (C3H4\text{C}_3\text{H}_4) = 3×12+4×1=40 g mol−13 \times 12 + 4 \times 1 = 40\text{ g mol}^{-1}.
    • Given mass of P=4.0 g\mathbf{P} = 4.0\text{ g}.
    • Moles of P=4.0 g40 g mol−1=0.1 mol\mathbf{P} = \frac{4.0\text{ g}}{40\text{ g mol}^{-1}} = 0.1\text{ mol}.
  2. Conversion of P\mathbf{P} to S\mathbf{S} (Hydration):

    • Propyne (P\mathbf{P}) reacts with Hg2+/H+\text{Hg}^{2+}/\text{H}^+ at 333 K333\text{ K} via Markovnikov addition of water followed by tautomerization to yield acetone (S\mathbf{S}): CH3−C≡CH+H2O→333 KHg2+/H+CH3−CO−CH3\text{CH}_3-\text{C}\equiv\text{CH} + \text{H}_2\text{O} \xrightarrow[\text{333 K}]{\text{Hg}^{2+}/\text{H}^+} \text{CH}_3-\text{CO}-\text{CH}_3
    • Percentage yield of this step = 100%100\%.
    • Moles of S\mathbf{S} formed = 0.1 mol×1.00=0.1 mol0.1\text{ mol} \times 1.00 = 0.1\text{ mol}.
  3. Conversion of S\mathbf{S} to T\mathbf{T} (Aldol Condensation):

    • Acetone (S\mathbf{S}) undergoes self-aldol condensation in the presence of Ba(OH)2\text{Ba(OH)}_2 followed by dehydration on heating to form mesityl oxide (T\mathbf{T}): 2CH3−CO−CH3→heatBa(OH)2(CH3)2C=CH−CO−CH3+H2O2\text{CH}_3-\text{CO}-\text{CH}_3 \xrightarrow[\text{heat}]{\text{Ba(OH)}_2} (\text{CH}_3)_2\text{C}=\text{CH}-\text{CO}-\text{CH}_3 + \text{H}_2\text{O}
    • Stoichiometric ratio: 2 moles of S→1 mole of T2\text{ moles of }\mathbf{S} \rightarrow 1\text{ mole of }\mathbf{T}.
    • Theoretical yield of T=0.1 mol2=0.05 mol\mathbf{T} = \frac{0.1\text{ mol}}{2} = 0.05\text{ mol}.
    • Given percentage yield = 80%80\%.
    • Actual moles of T\mathbf{T} obtained = 0.05 mol×0.80=0.04 mol0.05\text{ mol} \times 0.80 = 0.04\text{ mol}.
  4. Conversion of T\mathbf{T} to U\mathbf{U} (Haloform Reaction):

    • Mesityl oxide (T\mathbf{T}) contains a methyl ketone group (−CO−CH3-\text{CO}-\text{CH}_3) and reacts with NaOCl\text{NaOCl} via the haloform reaction to form 3-methylbut-2-enoic acid (U\mathbf{U}) which decolourises Baeyer's reagent due to the carbon-carbon double bond: (CH3)2C=CH−CO−CH3→NaOCl(CH3)2C=CH−COOH+CHCl3(\text{CH}_3)_2\text{C}=\text{CH}-\text{CO}-\text{CH}_3 \xrightarrow{\text{NaOCl}} (\text{CH}_3)_2\text{C}=\text{CH}-\text{COOH} + \text{CHCl}_3
    • Stoichiometric ratio: 1 mole of T→1 mole of U1\text{ mole of }\mathbf{T} \rightarrow 1\text{ mole of }\mathbf{U}.
    • Theoretical yield of U=0.04 mol\mathbf{U} = 0.04\text{ mol}.
    • Given percentage yield = 80%80\%.
    • Actual moles of U\mathbf{U} obtained = 0.04 mol×0.80=0.032 mol0.04\text{ mol} \times 0.80 = 0.032\text{ mol}.
  5. Calculation of the Mass of Product U\mathbf{U} (yy):

    • Molecular formula of 3-methylbut-2-enoic acid (U\mathbf{U}) is C5H8O2\text{C}_5\text{H}_8\text{O}_2.
    • Molar mass of U=5(12)+8(1)+2(16)=60+8+32=100 g mol−1\mathbf{U} = 5(12) + 8(1) + 2(16) = 60 + 8 + 32 = 100\text{ g mol}^{-1}.
    • Mass of U\mathbf{U} (yy) = moles of U×molar mass of U\text{moles of }\mathbf{U} \times \text{molar mass of }\mathbf{U}: y=0.032 mol×100 g mol−1=3.20 gy = 0.032\text{ mol} \times 100\text{ g mol}^{-1} = 3.20\text{ g}

Thus, the value of y\mathbf{y} is 3.203.20 (or 3.23.2).