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Alcohols Phenols and Ethers question

2025 · Shift 1 · Q13
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Alcohols Phenols and Ethers question

2025 · Shift 1 · Q13

JEE AdvancedChemistryAlcohols Phenols and EthersNumerical+4 / −1
The reaction sequence given below is carried out with 16 moles of X. The yield of the major product in each step is given below the product in parentheses. The amount (in grams) of S produced is ‾\underline{\hspace{2cm}}​. JEE Advanced 2025 Paper 1 Online Chemistry - Alcohols, Phenols and Ethers Question 1 EnglishUse: Atomic mass (in amu): H = 1, C = 12, O = 16, Br = 80
Numerical answer
View written solutionFree

Correct answer: 1116

Step-by-Step Solution

The problem asks for the amount of the final product S in grams, starting from 16 moles of compound X (Phenol). The reaction sequence and yield for each step are given.

Step 1: Identify the reactants and products in each step.

  1. X → P: The starting material X is phenol (C6H5OHC_6H_5OHC6​H5​OH). The reagents are NaOHNaOHNaOH followed by CH3BrCH_3BrCH3​Br. This is a Williamson Ether Synthesis. Phenol, being acidic, reacts with NaOHNaOHNaOH to form sodium phenoxide (C6H5O−Na+C_6H_5O^-Na^+C6​H5​O−Na+), which then acts as a nucleophile and attacks CH3BrCH_3BrCH3​Br to form an ether.

    • Product P is Anisole (methoxybenzene), C6H5OCH3C_6H_5OCH_3C6​H5​OCH3​. The yield is 80%.
  2. P → Q: The reagent is Br2Br_2Br2​ in the presence of FeFeFe (a Lewis acid catalyst, forming FeBr3FeBr_3FeBr3​ in situ). This is an electrophilic aromatic substitution (bromination). The methoxy group (−OCH3-OCH_3−OCH3​) is a strongly activating, ortho-para directing group. The major product is the para isomer due to less steric hindrance.

    • Product Q is p-Bromoanisole (4-bromoanisole), p−Br−C6H4−OCH3p-Br-C_6H_4-OCH_3p−Br−C6​H4​−OCH3​. The yield is 75%.
  3. Q → R: The reagents are MgMgMg and dry ether. This reaction forms a Grignard reagent.

    • Product R is p-methoxyphenylmagnesium bromide, p−CH3O−C6H4−MgBrp-CH_3O-C_6H_4-MgBrp−CH3​O−C6​H4​−MgBr. The yield is 90%.
  4. R → S: The reagents are acetaldehyde (CH3CHOCH_3CHOCH3​CHO) followed by an acidic workup (H3O+H_3O^+H3​O+). The Grignard reagent (R) attacks the electrophilic carbonyl carbon of acetaldehyde, followed by protonation of the resulting alkoxide.

    • Product S is 1-(4-methoxyphenyl)ethanol, p−CH3O−C6H4−CH(OH)CH3p-CH_3O-C_6H_4-CH(OH)CH_3p−CH3​O−C6​H4​−CH(OH)CH3​. The yield is 85%.

Step 2: Calculate the molar mass of the final product S.

  • The chemical formula for S, 1-(4-methoxyphenyl)ethanol, is C9H12O2C_9H_{12}O_2C9​H12​O2​.
  • Using the given atomic masses (C=12, H=1, O=16): Molar Mass of S=(9×12)+(12×1)+(2×16)=108+12+32=152 g/mol\text{Molar Mass of S} = (9 \times 12) + (12 \times 1) + (2 \times 16) = 108 + 12 + 32 = 152 \text{ g/mol}Molar Mass of S=(9×12)+(12×1)+(2×16)=108+12+32=152 g/mol

Step 3: Calculate the overall molar yield and the moles of S produced.

  • The initial amount of X is 16 moles.
  • The yields are applied sequentially. The overall yield is the product of the individual yields. Overall Yield=0.80×0.75×0.90×0.85\text{Overall Yield} = 0.80 \times 0.75 \times 0.90 \times 0.85Overall Yield=0.80×0.75×0.90×0.85 Overall Yield=0.60×0.90×0.85=0.54×0.85=0.459\text{Overall Yield} = 0.60 \times 0.90 \times 0.85 = 0.54 \times 0.85 = 0.459Overall Yield=0.60×0.90×0.85=0.54×0.85=0.459
  • The moles of S produced are calculated by multiplying the initial moles of X by the overall yield. Moles of S=Initial Moles of X×Overall Yield\text{Moles of S} = \text{Initial Moles of X} \times \text{Overall Yield}Moles of S=Initial Moles of X×Overall Yield Moles of S=16 mol×0.459=7.344 mol\text{Moles of S} = 16 \text{ mol} \times 0.459 = 7.344 \text{ mol}Moles of S=16 mol×0.459=7.344 mol

Step 4: Calculate the mass of S produced.

  • The mass of S is the product of its moles and molar mass. Mass of S=Moles of S×Molar Mass of S\text{Mass of S} = \text{Moles of S} \times \text{Molar Mass of S}Mass of S=Moles of S×Molar Mass of S Mass of S=7.344 mol×152 g/mol=1116.288 g\text{Mass of S} = 7.344 \text{ mol} \times 152 \text{ g/mol} = 1116.288 \text{ g}Mass of S=7.344 mol×152 g/mol=1116.288 g

Step 5: Final Answer.

The question asks for the amount in grams, and this is an integer-type question, so we round the result to the nearest integer.

Amount of S=1116 g\text{Amount of S} = 1116 \text{ g}Amount of S=1116 g

Comparison with Stored Answer

The calculated answer based on the problem statement is 1116 g. The stored correct answer is 175. There is a significant discrepancy.

The calculation has been thoroughly checked. The source of the discrepancy is likely a typo in the problem statement. If we assume the initial amount of X was 2.5 moles instead of 16 moles, the calculation would be:

  • Moles of S = 2.5 mol×0.459=1.1475 mol2.5 \text{ mol} \times 0.459 = 1.1475 \text{ mol}2.5 mol×0.459=1.1475 mol
  • Mass of S = 1.1475 mol×152 g/mol=174.42 g1.1475 \text{ mol} \times 152 \text{ g/mol} = 174.42 \text{ g}1.1475 mol×152 g/mol=174.42 g

This value (174.42 g) is very close to the stored answer of 175 g, with the small difference likely due to rounding in the given yield percentages. However, based on the question as written (with 16 moles of X), the correct answer is 1116 g.

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