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Alcohols Phenols and Ethers question

2006 · Shift 0 · Q23
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Alcohols Phenols and Ethers question

2006 · Shift 0 · Q23

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
The structure of the compound that gives a tribromo derivative on treatment with bromine water is
  1. A
    AIEEE 2006 Chemistry - Alcohols, Phenols and Ethers Question 150 English Option 1
  2. B
    AIEEE 2006 Chemistry - Alcohols, Phenols and Ethers Question 150 English Option 2
  3. C
    AIEEE 2006 Chemistry - Alcohols, Phenols and Ethers Question 150 English Option 3
  4. D
    AIEEE 2006 Chemistry - Alcohols, Phenols and Ethers Question 150 English Option 4
View written solutionFree

Correct answer: C

  1. Key idea: reaction with bromine water

    Compounds that give a tribromo derivative with bromine water are typically phenols (or highly activated aromatic rings).

    The classic reaction is: Phenol+3Br2→bromine water2,4,6-tribromophenol+3HBr\text{Phenol} + 3Br_2 \xrightarrow{\text{bromine water}} 2,4,6\text{-tribromophenol} + 3HBrPhenol+3Br2​bromine water​2,4,6-tribromophenol+3HBr

  2. Why does phenol react this way?

    The −OH-OH−OH group in phenol strongly activates the benzene ring by resonance and directs electrophilic substitution to the ortho and para positions.

    Therefore, in bromine water, substitution occurs rapidly at all three activated positions:

    • position 2
    • position 4
    • position 6

    giving a tribromo derivative.

  3. Identification of the required structure

    Since the question asks for the structure that gives a tribromo derivative with bromine water, the correct structure must be phenol (or an equivalent strongly activating phenolic structure).

  4. Matching with the given options

    The stored correct answer is C, so option C must correspond to the phenolic structure that forms 2,4,62,4,62,4,6-tribromo derivative.

  5. Conclusion

    Hence, the compound is Option C.

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