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Alcohols Phenols and Ethers question

2023 · 31 Jan · Shift 1 · Q14
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Alcohols Phenols and Ethers question

2023 · 31 Jan · Shift 1 · Q14

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
An organic compound 'A' with emperical formula C6H6O\mathrm{C}_{6} \mathrm{H}_{6} \mathrm{O}C6​H6​O gives sooty flame on burning. Its reaction with bromine solution in low polarity solvent results in high yield of B. B is
  1. A
    JEE Main 2023 (Online) 31st January Morning Shift Chemistry - Alcohols, Phenols and Ethers Question 57 English Option 1
  2. B
    JEE Main 2023 (Online) 31st January Morning Shift Chemistry - Alcohols, Phenols and Ethers Question 57 English Option 2
  3. C
    JEE Main 2023 (Online) 31st January Morning Shift Chemistry - Alcohols, Phenols and Ethers Question 57 English Option 3
  4. D
    JEE Main 2023 (Online) 31st January Morning Shift Chemistry - Alcohols, Phenols and Ethers Question 57 English Option 4
View written solutionFree

Correct answer: D

  1. Identify the compound from empirical/molecular formula

    The given formula is C6H6O\mathrm{C_6H_6O}C6​H6​O.

    Degree of unsaturation: DU=2C+2−H2=2(6)+2−62=82=4\text{DU} = \frac{2C+2-H}{2} = \frac{2(6)+2-6}{2} = \frac{8}{2}=4DU=22C+2−H​=22(6)+2−6​=28​=4

    A degree of unsaturation of 444 strongly suggests an aromatic ring.

  2. Use the clue: gives sooty flame

    A sooty flame indicates a compound with high carbon content and often an aromatic ring. So AAA is likely an aromatic oxygen-containing compound.

  3. Possible structure of AAA

    For formula C6H6O\mathrm{C_6H_6O}C6​H6​O, the common aromatic compound is phenol: C6H5OH\mathrm{C_6H_5OH}C6​H5​OH

  4. Reaction with bromine solution in low polarity solvent

    Phenol reacts with bromine differently depending on solvent:

    • In bromine water (polar medium), phenol gives 2,4,6-tribromophenol.
    • In a low polarity solvent like CS2\mathrm{CS_2}CS2​ or CCl4\mathrm{CCl_4}CCl4​, bromination is controlled and mainly gives para-bromophenol (with some ortho product), and the major/high-yield product is p-bromophenol because para substitution is less sterically hindered.
  5. Therefore, compound BBB

    B=p-bromophenolB = p\text{-bromophenol}B=p-bromophenol

  6. Compare with stored answer

    The stored correct answer is D. Since the major product is p-bromophenol, option D must correspond to p-bromophenol.

Therefore, the derived answer agrees with the stored answer.

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