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Alcohols Phenols and Ethers question

2024 · 6 Apr · Shift 1 · Q16
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Alcohols Phenols and Ethers question

2024 · 6 Apr · Shift 1 · Q16

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
In Reimer - Tiemann reaction, phenol is converted into salicylaldehyde through an intermediate. The structure of intermediate is ‾\underline{\hspace{2cm}}​.
  1. A
    JEE Main 2024 (Online) 6th April Morning Shift Chemistry - Alcohols, Phenols and Ethers Question 8 English Option 1
  2. B
    JEE Main 2024 (Online) 6th April Morning Shift Chemistry - Alcohols, Phenols and Ethers Question 8 English Option 2
  3. C
    JEE Main 2024 (Online) 6th April Morning Shift Chemistry - Alcohols, Phenols and Ethers Question 8 English Option 3
  4. D
    JEE Main 2024 (Online) 6th April Morning Shift Chemistry - Alcohols, Phenols and Ethers Question 8 English Option 4
View written solutionFree

Correct answer: B

  1. Recall the Reimer–Tiemann reaction

    Phenol reacts with chloroform in aqueous alkali to give mainly o-hydroxybenzaldehyde (salicylaldehyde).

    The important reactive species generated is dichlorocarbene, :CCl2:CCl_2:CCl2​.

  2. Formation of the electrophile

    In base, chloroform gives dichlorocarbene: CHCl3+OH−→:CCl2+Cl−+H2OCHCl_3 + OH^- \rightarrow :CCl_2 + Cl^- + H_2OCHCl3​+OH−→:CCl2​+Cl−+H2​O

  3. Reaction with phenoxide ion

    Phenol in alkali forms phenoxide ion, which is strongly activating and directs electrophilic substitution at the ortho and para positions.

    Dichlorocarbene attacks mainly at the ortho position to give an intermediate of the type: o-HO−C6H4−CHCl2o\text{-}HO{-}C_6H_4{-}CHCl_2o-HO−C6​H4​−CHCl2​

    This is o-hydroxybenzal chloride.

  4. Hydrolysis of the intermediate

    The −CHCl2-CHCl_2−CHCl2​ group hydrolyzes under the reaction conditions to the aldehyde group −CHO-CHO−CHO: o-HO−C6H4−CHCl2→hydrolysiso-HO−C6H4−CHOo\text{-}HO{-}C_6H_4{-}CHCl_2 \xrightarrow{hydrolysis} o\text{-}HO{-}C_6H_4{-}CHOo-HO−C6​H4​−CHCl2​hydrolysis​o-HO−C6​H4​−CHO

    Thus salicylaldehyde is formed through the intermediate o-hydroxybenzal chloride.

  5. Conclusion

    Therefore, the required intermediate is: o-HO−C6H4−CHCl2\boxed{o\text{-}HO{-}C_6H_4{-}CHCl_2}o-HO−C6​H4​−CHCl2​​

    Since the stored correct answer is B, the structure corresponding to B must be o-hydroxybenzal chloride.

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