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Alcohols Phenols and Ethers question

2024 · 29 Jan · Shift 2 · Q17
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Alcohols Phenols and Ethers question

2024 · 29 Jan · Shift 2 · Q17

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
Phenol treated with chloroform in presence of sodium hydroxide, which further hydrolyzed in presence of an acid results
  1. A
    Salicylic acid
  2. B
    Benzene-1,2-diol
  3. C
    2-Hydroxybenzaldehyde
  4. D
    Benzene-1,3-diol
View written solutionFree

Correct answer: C

  1. Identify the reaction

Phenol treated with chloroform (CHCl3\mathrm{CHCl_3}CHCl3​) in the presence of sodium hydroxide (NaOH\mathrm{NaOH}NaOH), followed by hydrolysis/acidification, is the Reimer–Tiemann reaction.

  1. What happens in Reimer–Tiemann reaction?

In this reaction, phenol first forms phenoxide ion in basic medium:

C6H5OH+NaOH→C6H5O−Na++H2O\mathrm{C_6H_5OH + NaOH \rightarrow C_6H_5O^-Na^+ + H_2O}C6​H5​OH+NaOH→C6​H5​O−Na++H2​O

Chloroform in strong base generates dichlorocarbene (:CCl2: \mathrm{CCl_2}:CCl2​), which acts as the electrophile.

The formyl group is introduced mainly at the ortho position of phenol, and after hydrolysis gives o-hydroxybenzaldehyde.

  1. Main product formed

Thus, phenol gives:

C6H5OH→NaOHCHCl3oext−HO−C6H4−CHO\mathrm{C_6H_5OH \xrightarrow[NaOH]{CHCl_3} o ext{-}HO{-}C_6H_4{-}CHO}C6​H5​OHCHCl3​NaOH​oext−HO−C6​H4​−CHO

This compound is 2-hydroxybenzaldehyde (also called salicylaldehyde).

  1. Check the options
  • A: Salicylic acid →\rightarrow→ This is formed in the Kolbe reaction using CO2/NaOH\mathrm{CO_2/NaOH}CO2​/NaOH, not here. Incorrect.
  • B: Benzene-1,2-diol →\rightarrow→ Catechol, not formed in Reimer–Tiemann reaction. Incorrect.
  • C: 2-Hydroxybenzaldehyde →\rightarrow→ Correct.
  • D: Benzene-1,3-diol →\rightarrow→ Resorcinol, not formed here. Incorrect.
  1. Final answer

The product obtained is 2-hydroxybenzaldehyde.

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