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(D) $PhCH_2OH$ is the least acidic because its conjugate base is not stabilized by resonance like the others.Conjugate bases of $PhSO_3H$ and $PhCOOH$

Vedclass · Accepted Answer

$PhSO_3H > PhCO_2H > PhOH > PhCH_2OH$

Vedclass · Answer

(D) $PhCH_2OH$ is the least acidic because its conjugate base is not stabilized by resonance like the others.Conjugate bases of $PhSO_3H$ and $PhCOOH$ have equivalent resonance structures,whereas the conjugate base of $PhOH$ (phenoxide ion) has non-equivalent resonance structures.Furthermore,in the phenoxide ion,the negative charge is delocalized on carbon atoms,whereas in the conjugate bases of $PhSO_3H$ and $PhCOOH$,the negative charge is delocalized on highly electronegative oxygen atoms,making $PhSO_3H$ and $PhCOOH$ stronger acids than $PhOH$.Comparing $PhSO_3H$ and $PhCOOH$,the conjugate base of $PhSO_3H$ (sulfonate ion) has $3$ equivalent resonance structures,while the conjugate base of $PhCOOH$ (carboxylate ion) has $2$ equivalent resonance structures.Greater the number of equivalent resonance structures,the higher the stability of the conjugate base.Stability of conjugate base $\propto$ Acidity.Therefore,the correct decreasing order of acidity is $PhSO_3H > PhCO_2H > PhOH > PhCH_2OH$.

Which of the following shows the correct order of decreasing acidity?

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