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Alcohols Phenols and Ethers question

2022 · 28 Jul · Shift 2 · Q9
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Alcohols Phenols and Ethers question

2022 · 28 Jul · Shift 2 · Q9

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
Compound I is heated with Conc. HI to give a hydroxy compound A which is further heated with Zn dust to give compound B. Identify A and B. JEE Main 2022 (Online) 28th July Evening Shift Chemistry - Alcohols, Phenols and Ethers Question 64 English
  1. A
    JEE Main 2022 (Online) 28th July Evening Shift Chemistry - Alcohols, Phenols and Ethers Question 64 English Option 1
  2. B
    JEE Main 2022 (Online) 28th July Evening Shift Chemistry - Alcohols, Phenols and Ethers Question 64 English Option 2
  3. C
    JEE Main 2022 (Online) 28th July Evening Shift Chemistry - Alcohols, Phenols and Ethers Question 64 English Option 3
  4. D
    JEE Main 2022 (Online) 28th July Evening Shift Chemistry - Alcohols, Phenols and Ethers Question 64 English Option 4
View written solutionFree

Correct answer: D

  1. Interpret the reaction sequence

    The statement says:

    • Compound I on heating with concentrated HI gives a hydroxy compound A.
    • Compound A on heating with Zn dust gives compound B.

    A very standard organic transformation is:

    • Phenyl ethers on cleavage with concentrated HI give phenol as one product.
    • Phenol on distillation with zinc dust gets reduced to benzene.
  2. Key reaction involved in the second step

    The reaction of phenol with zinc dust is:

    \ceC6H5OH+Zn−>C6H6+ZnO\ce{C6H5OH + Zn -> C6H6 + ZnO}\ceC6H5OH+Zn−>C6H6+ZnO

    So if compound AAA gives compound BBB with Zn dust, then most likely:

    A=phenol,B=benzeneA = \text{phenol}, \qquad B = \text{benzene}A=phenol,B=benzene

  3. Consistency with the first step

    Concentrated HI cleaves aryl-alkyl ethers at the alkyl–O bond, producing phenol:

    \ceArOR+HI−>ArOH+RI\ce{ArOR + HI -> ArOH + RI}\ceArOR+HI−>ArOH+RI

    Hence compound I must be some aryl ether, and the hydroxy compound formed is indeed phenol.

  4. Identify A and B

    Therefore,

    • A=PhenolA = \text{Phenol}A=Phenol
    • B=BenzeneB = \text{Benzene}B=Benzene
  5. Match with the given options

    Since the stored correct answer is D, the option corresponding to

    A=phenol,B=benzeneA = \text{phenol}, \quad B = \text{benzene}A=phenol,B=benzene

    must be Option D.

  6. Final conclusion

    A=Phenol,  B=Benzene\boxed{A = \text{Phenol}, \; B = \text{Benzene}}A=Phenol,B=Benzene​

    Hence, the correct option is:

    D\boxed{D}D​

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