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Alcohols Phenols and Ethers question

2009 · Shift 0 · Q14
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Alcohols Phenols and Ethers question

2009 · Shift 0 · Q14

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
The major product obtained on interaction of phenol with sodium hydroxide and carbon dioxide is :
  1. A
    benzoic acid
  2. B
    salicylaldehyde
  3. C
    salicylic acid
  4. D
    phthalic acid
View written solutionFree

Correct answer: C

  1. Identify the reaction
    Phenol reacts with sodium hydroxide to form sodium phenoxide:

C6H5OH+NaOH→C6H5ONa+H2O\mathrm{C_6H_5OH + NaOH \rightarrow C_6H_5ONa + H_2O}C6​H5​OH+NaOH→C6​H5​ONa+H2​O

  1. Reaction with carbon dioxide
    When sodium phenoxide is treated with carbon dioxide under pressure and then acidified, it undergoes the Kolbe–Schmitt reaction.

C6H5ONa+CO2→pressureheatoext−HO−C6H4COONa\mathrm{C_6H_5ONa + CO_2 \xrightarrow[pressure]{heat} o ext{-}HO{-}C_6H_4COONa}C6​H5​ONa+CO2​heatpressure​oext−HO−C6​H4​COONa

On acidification:

oext−HO−C6H4COONa+H+→oext−HO−C6H4COOH\mathrm{o ext{-}HO{-}C_6H_4COONa + H^+ \rightarrow o ext{-}HO{-}C_6H_4COOH}oext−HO−C6​H4​COONa+H+→oext−HO−C6​H4​COOH

This product is salicylic acid.

  1. Why this is the major product
    In the Kolbe–Schmitt reaction, carboxylation occurs mainly at the ortho position to the phenoxide group, giving o-hydroxybenzoic acid (salicylic acid) as the major product.

  2. Check options

  • A: benzoic acid — incorrect, no hydroxyl group on ring.
  • B: salicylaldehyde — incorrect, this is formed in Reimer–Tiemann reaction, not with CO2\mathrm{CO_2}CO2​.
  • C: salicylic acid — correct.
  • D: phthalic acid — incorrect.

Therefore, the major product is:

salicylic acid\boxed{\text{salicylic acid}}salicylic acid​

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