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Q.Give reason -

(a) Phenol is more acidic in comparison to Ethyl Alcohol. Why?
(b) Ether is less soluble in water but more soluble in concentrated H2SO4H_2SO_4. Why?
Uttarakhand UbseUttarakhand Board Intermediate (Class 12) 2024Subjective· 2mImportance★★★★★
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Resonance stabilisation of the phenoxide ion makes phenol more acidic than ethanol; ether's basic oxygen lone pair explains its differing solubility in water vs conc. H2SO4H_2SO_4.

(a) In phenol, the −OH-OH group is directly attached to the benzene ring. The lone pair of electrons on the oxygen atom is delocalised (conjugated) into the aromatic ring through resonance; this withdraws electron density from oxygen, making the O–H bond more polar and easier to break. More importantly, after loss of H+H^+, the resulting phenoxide ion (C6H5O−C_6H_5O^-) is stabilised by resonance — the negative charge is delocalised over the ortho and para carbons of the ring, spreading out the charge and lowering the ion's energy. In ethanol, no such resonance stabilisation of the ethoxide ion (C2H5O−C_2H_5O^-) is possible; instead, the +I+I (electron-donating) effect of the ethyl group increases electron density on oxygen, making it less willing to release H+H^+. Hence phenol (pKa≈10pK_a \approx 10) is significantly more acidic than ethanol (pKa≈16pK_a \approx 16).

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