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Hydrocarbons question

2021 · Shift 1 · Q5
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Hydrocarbons question

2021 · Shift 1 · Q5

JEE AdvancedChemistryHydrocarbonsNumerical+2 / −1
For the following reaction scheme, percentage yields are given along the arrow: JEE Advanced 2021 Paper 1 Online Chemistry - Hydrocarbons Question 20 English x g and y g are mass of R and U, respectively. (Use : Molar mass (in g mol −-− 1) of H, C and O as 1, 12 and 16, respectively) The value of x is ‾\underline{\hspace{2cm}}​.
Numerical answer
View written solutionFree

Correct answer: 5.664

The user wants me to solve a multi-step organic synthesis problem and calculate the mass of product R, denoted by 'x'.

Step 1: Identify the structures and molar masses of the compounds.

  • P: 1-phenylethanone (Acetophenone). Its structure is C6H5−CO−CH3C_6H_5-CO-CH_3C6​H5​−CO−CH3​. Molar mass (M_P) = (8×12)+(8×1)+16=120(8 \times 12) + (8 \times 1) + 16 = 120(8×12)+(8×1)+16=120 g/mol.
  • Reaction P → Q: This is a Grignard reaction. The nucleophile CH3−CH_3^-CH3−​ from CH3MgBrCH_3MgBrCH3​MgBr attacks the carbonyl carbon of P, followed by protonation. C6H5−CO−CH3+CH3MgBr→C6H5−C(O−MgBr+)(CH3)2→H3O+C6H5−C(OH)(CH3)2C_6H_5-CO-CH_3 + CH_3MgBr \rightarrow C_6H_5-C(O^-MgBr^+)(CH_3)_2 \xrightarrow{H_3O^+} C_6H_5-C(OH)(CH_3)_2C6​H5​−CO−CH3​+CH3​MgBr→C6​H5​−C(O−MgBr+)(CH3​)2​H3​O+​C6​H5​−C(OH)(CH3​)2​
  • Q: 2-phenylpropan-2-ol. Its structure is C6H5−C(OH)(CH3)2C_6H_5-C(OH)(CH_3)_2C6​H5​−C(OH)(CH3​)2​. Molar mass (M_Q) = (9×12)+(12×1)+16=136(9 \times 12) + (12 \times 1) + 16 = 136(9×12)+(12×1)+16=136 g/mol.
  • Reaction Q → R: This is an acid-catalyzed dehydration (E1 mechanism) of a tertiary alcohol to form an alkene. The most stable alkene is the major product. Here, elimination of a proton from either of the two methyl groups gives the same product. C6H5−C(OH)(CH3)2→H2SO4C6H5−C(CH3)=CH2+H2OC_6H_5-C(OH)(CH_3)_2 \xrightarrow{H_2SO_4} C_6H_5-C(CH_3)=CH_2 + H_2OC6​H5​−C(OH)(CH3​)2​H2​SO4​​C6​H5​−C(CH3​)=CH2​+H2​O
  • R: 2-phenylpropene (α-methylstyrene). This is the major product. Molar mass (M_R) = (9×12)+(10×1)=118(9 \times 12) + (10 \times 1) = 118(9×12)+(10×1)=118 g/mol.
  • Reaction R → T + U: This is a reductive ozonolysis reaction, which cleaves the double bond. C6H5−C(CH3)=CH2→1.O3,2.Zn,H2OC6H5−C(=O)CH3+HCHOC_6H_5-C(CH_3)=CH_2 \xrightarrow{1. O_3, 2. Zn, H_2O} C_6H_5-C(=O)CH_3 + HCHOC6​H5​−C(CH3​)=CH2​1.O3​,2.Zn,H2​O​C6​H5​−C(=O)CH3​+HCHO
  • T: 1-phenylethanone (same as P).
  • U: Formaldehyde (HCHO). Molar mass (M_U) = 12+(2×1)+16=3012 + (2 \times 1) + 16 = 3012+(2×1)+16=30 g/mol.

Step 2: Calculate the initial moles of P.

The initial mass of P is given as 12 g. nP=mass of PMP=12 g120 g/mol=0.1 moln_P = \frac{\text{mass of P}}{M_P} = \frac{12 \text{ g}}{120 \text{ g/mol}} = 0.1 \text{ mol}nP​=MP​mass of P​=120 g/mol12 g​=0.1 mol

Step 3: Calculate the moles of Q produced.

The reaction P→QP \rightarrow QP→Q has a yield of 80%. The stoichiometry is 1:1. nQ=nP×80100=0.1 mol×0.80=0.08 moln_Q = n_P \times \frac{80}{100} = 0.1 \text{ mol} \times 0.80 = 0.08 \text{ mol}nQ​=nP​×10080​=0.1 mol×0.80=0.08 mol

Step 4: Calculate the moles of R produced.

The reaction Q→RQ \rightarrow RQ→R has a yield of 60% for the major product R. The stoichiometry is 1:1. nR=nQ×60100=0.08 mol×0.60=0.048 moln_R = n_Q \times \frac{60}{100} = 0.08 \text{ mol} \times 0.60 = 0.048 \text{ mol}nR​=nQ​×10060​=0.08 mol×0.60=0.048 mol

Step 5: Calculate the mass of R (x).

The mass of R is x. We can calculate it using the moles of R and its molar mass. x=nR×MR=0.048 mol×118 g/mol=5.664 gx = n_R \times M_R = 0.048 \text{ mol} \times 118 \text{ g/mol} = 5.664 \text{ g}x=nR​×MR​=0.048 mol×118 g/mol=5.664 g

The value of x is 5.664 g.

Answer Verification:

The question asks for the value of x. My calculated value is 5.664. The stored correct answer is 1.62. These values do not match.

Let's analyze the discrepancy. The steps and chemical principles used are standard. Let's assume the stored answer 1.62 is correct and see what it implies. If x = 1.62 g, then: nR=1.62 g118 g/mol≈0.01373 moln_R = \frac{1.62 \text{ g}}{118 \text{ g/mol}} \approx 0.01373 \text{ mol}nR​=118 g/mol1.62 g​≈0.01373 mol Working backwards: nQ=nR0.60=0.013730.60≈0.02288 moln_Q = \frac{n_R}{0.60} = \frac{0.01373}{0.60} \approx 0.02288 \text{ mol}nQ​=0.60nR​​=0.600.01373​≈0.02288 mol nP=nQ0.80=0.022880.80≈0.0286 moln_P = \frac{n_Q}{0.80} = \frac{0.02288}{0.80} \approx 0.0286 \text{ mol}nP​=0.80nQ​​=0.800.02288​≈0.0286 mol Required initial mass of P would be: mass of P=nP×MP=0.0286 mol×120 g/mol≈3.43 g\text{mass of P} = n_P \times M_P = 0.0286 \text{ mol} \times 120 \text{ g/mol} \approx 3.43 \text{ g}mass of P=nP​×MP​=0.0286 mol×120 g/mol≈3.43 g This contradicts the given initial mass of 12 g.

There seems to be an error in the question's data (initial mass or yields) or the stored answer. It is worth noting that if the question asked for the mass of U (y) and the initial mass of P was 27 g, the calculation would be: nP=27/120=0.225 moln_P = 27/120 = 0.225 \text{ mol}nP​=27/120=0.225 mol nQ=0.225×0.8=0.18 moln_Q = 0.225 \times 0.8 = 0.18 \text{ mol}nQ​=0.225×0.8=0.18 mol nR=0.18×0.6=0.108 moln_R = 0.18 \times 0.6 = 0.108 \text{ mol}nR​=0.18×0.6=0.108 mol nU=nR×0.5=0.108×0.5=0.054 moln_U = n_R \times 0.5 = 0.108 \times 0.5 = 0.054 \text{ mol}nU​=nR​×0.5=0.108×0.5=0.054 mol y=nU×MU=0.054×30=1.62 gy = n_U \times M_U = 0.054 \times 30 = 1.62 \text{ g}y=nU​×MU​=0.054×30=1.62 g This matches the stored answer. However, based on the question as provided, my calculated value for x is correct.

Final Answer based on the problem statement: x = 5.664 g.

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