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Alcohols Phenols and Ethers question

2024 · 8 Apr · Shift 2 · Q5
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  5. /2024 · 8 Apr · Shift 2 · Q5

Alcohols Phenols and Ethers question

2024 · 8 Apr · Shift 2 · Q5

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
Which one the following compounds will readily react with dilute NaOH\mathrm{NaOH}NaOH ?
  1. A
    C6H5CH2OH\mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}_2 \mathrm{OH}C6​H5​CH2​OH
  2. B
    C2H5OH\mathrm{C}_2 \mathrm{H}_5 \mathrm{OH}C2​H5​OH
  3. C
    C6H5OH\mathrm{C}_6 \mathrm{H}_5 \mathrm{OH}C6​H5​OH
  4. D
    (CH3)3COH\left(\mathrm{CH}_3\right)_3 \mathrm{COH}(CH3​)3​COH
View written solutionFree

Correct answer: C

  1. Concept involved

A compound will react readily with dilute NaOH\mathrm{NaOH}NaOH if it is sufficiently acidic to donate a proton to OH−\mathrm{OH^-}OH−.

So we compare the acidity of the given alcohols/phenol.


  1. Check each option

Option A: C6H5CH2OH\mathrm{C_6H_5CH_2OH}C6​H5​CH2​OH (benzyl alcohol)

This is an alcohol. Ordinary alcohols are very weak acids and do not react readily with dilute NaOH\mathrm{NaOH}NaOH.

C6H5CH2OH+NaOH  ↛  significant reaction\mathrm{C_6H_5CH_2OH + NaOH \;\not\to\; significant\ reaction}C6​H5​CH2​OH+NaOH→significant reaction

So, A is incorrect.


Option B: C2H5OH\mathrm{C_2H_5OH}C2​H5​OH (ethanol)

Ethanol is also a typical alcohol and is even less acidic than phenol. It does not react readily with dilute NaOH\mathrm{NaOH}NaOH.

C2H5OH+NaOH  ↛  significant reaction\mathrm{C_2H_5OH + NaOH \;\not\to\; significant\ reaction}C2​H5​OH+NaOH→significant reaction

So, B is incorrect.


Option C: C6H5OH\mathrm{C_6H_5OH}C6​H5​OH (phenol)

Phenol is appreciably more acidic than ordinary alcohols because its conjugate base, phenoxide ion, is resonance stabilized.

Reaction:

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

Hence phenol reacts readily with dilute NaOH\mathrm{NaOH}NaOH.

So, C is correct.


Option D: (CH3)3COH\mathrm{(CH_3)_3COH}(CH3​)3​COH (tert-butyl alcohol)

This is also an alcohol and is not acidic enough to react with dilute NaOH\mathrm{NaOH}NaOH.

(CH3)3COH+NaOH  ↛  significant reaction\mathrm{(CH_3)_3COH + NaOH \;\not\to\; significant\ reaction}(CH3​)3​COH+NaOH→significant reaction

So, D is incorrect.


  1. Why phenol reacts but alcohols do not
  • Phenol forms phenoxide ion: C6H5O−\mathrm{C_6H_5O^-}C6​H5​O− which is stabilized by resonance.
  • Alcohols form alkoxide ions: RO−\mathrm{RO^-}RO− which are not resonance stabilized.

Therefore, phenol is acidic enough to react with dilute NaOH\mathrm{NaOH}NaOH, whereas normal alcohols are not.


  1. Final answer

The compound that readily reacts with dilute NaOH\mathrm{NaOH}NaOH is:

C6H5OH\boxed{\mathrm{C_6H_5OH}}C6​H5​OH​

So, the correct option is C.

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