JEE Challenger
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Calculate Mass of Product R in Multi Step Hydrocarbon Reaction Scheme

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 x\mathbf{x}.

Question Diagram 1
Official Numerical Answer1.62

Step-by-Step Solution

To determine the mass of product R\mathbf{R} (x g\mathbf{x}\text{ g}), we analyze the step-by-step chemical transformations and stoichiometry:

Step 1: Identification of Compound P and calculation of its moles

Hydrolysis of magnesium dicarbide (Mg2C3\text{Mg}_2\text{C}_3) yields 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}

  • Compound P\mathbf{P}: Propyne (C3H4\text{C}_3\text{H}_4)
  • Molar mass of P\mathbf{P} (C3H4\text{C}_3\text{H}_4): Molar Mass=(3×12)+(4×1)=40 g mol−1\text{Molar Mass} = (3 \times 12) + (4 \times 1) = 40\text{ g mol}^{-1}
  • Given mass of P\mathbf{P}: 4.0 g4.0\text{ g}
  • Moles of P\mathbf{P}: nP=4.0 g40 g mol−1=0.1 moln_{\mathbf{P}} = \frac{4.0\text{ g}}{40\text{ g mol}^{-1}} = 0.1\text{ mol}

Step 2: Formation of Compound Q

Propyne (P\mathbf{P}) undergoes terminal alkyne deprotonation using NaNH2\text{NaNH}_2, followed by alkylation with methyl iodide (CH3I\text{CH}_3\text{I}) to form but-2-yne (Q\mathbf{Q}): CH3-C≡CH→NaNH2CH3-C≡C−Na+→CH3ICH3-C≡C-CH3\text{CH}_3\text{-C}\equiv\text{CH} \xrightarrow{\text{NaNH}_2} \text{CH}_3\text{-C}\equiv\text{C}^-\text{Na}^+ \xrightarrow{\text{CH}_3\text{I}} \text{CH}_3\text{-C}\equiv\text{C-CH}_3

  • Compound Q\mathbf{Q}: But-2-yne (C4H6\text{C}_4\text{H}_6)
  • Reaction yield: 75%75\%
  • Moles of Q\mathbf{Q} formed: nQ=nP×75100=0.1×0.75=0.075 moln_{\mathbf{Q}} = n_{\mathbf{P}} \times \frac{75}{100} = 0.1 \times 0.75 = 0.075\text{ mol}

Step 3: Trimerization of Q to form Compound R

Passing but-2-yne (Q\mathbf{Q}) through a red-hot iron tube at 873 K873\text{ K} causes cyclic trimerization to form hexamethylbenzene (R\mathbf{R}): 3 CH3-C≡C-CH3→873 Kred hot iron tubeC6(CH3)63\,\text{CH}_3\text{-C}\equiv\text{C-CH}_3 \xrightarrow[\text{873 K}]{\text{red hot iron tube}} \text{C}_6(\text{CH}_3)_6

  • Compound R\mathbf{R}: Hexamethylbenzene (C12H18\text{C}_{12}\text{H}_{18})
  • Stoichiometry: 3 moles of Q→1 mole of R3\text{ moles of } \mathbf{Q} \rightarrow 1\text{ mole of } \mathbf{R}
  • Theoretical moles of R\mathbf{R}: nR,theoretical=nQ3=0.0753=0.025 moln_{\mathbf{R, theoretical}} = \frac{n_{\mathbf{Q}}}{3} = \frac{0.075}{3} = 0.025\text{ mol}
  • Reaction yield: 40%40\%
  • Actual moles of R\mathbf{R}: nR,actual=0.025×40100=0.010 moln_{\mathbf{R, actual}} = 0.025 \times \frac{40}{100} = 0.010\text{ mol}

Step 4: Calculation of the Mass of Compound R (x\mathbf{x})

  • Molar mass of R\mathbf{R} (C12H18\text{C}_{12}\text{H}_{18}): Molar Mass=(12×12)+(18×1)=144+18=162 g mol−1\text{Molar Mass} = (12 \times 12) + (18 \times 1) = 144 + 18 = 162\text{ g mol}^{-1}
  • Mass of R\mathbf{R} (x g\mathbf{x}\text{ g}): x=nR,actual×Molar Mass of R=0.010 mol×162 g mol−1=1.62 g\mathbf{x} = n_{\mathbf{R, actual}} \times \text{Molar Mass of } \mathbf{R} = 0.010\text{ mol} \times 162\text{ g mol}^{-1} = 1.62\text{ g}

Final Answer: The value of x\mathbf{x} is 1.62