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Q.Assertion (A) : Phenol is less acidic than 4-methylphenol. Reason (R) : The presence of an electron releasing group in phenol makes it less acidic. Options : (A) Both Assertion (A) and Reason (R) are true and Reason (R) is the correct explanation of the Assertion (A). (B) Both Assertion (A) and Reason (R) are true, but Reason (R) is not the correct explanation of the Assertion (A). (C) Assertion (A) is true, but Reason (R) is false. (D) Assertion (A) is false, but Reason (R) is true.

CBSECBSE Class XII Board 2026MCQ· 1mImportance★★★★★
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Assertion (A) is false because electron-releasing groups like methyl decrease acidity, making 4-methylphenol less acidic than phenol. Reason (R) is true as electron-releasing groups indeed decrease acidity. The correct option is (D).

Understanding the acidity of organic compounds, especially phenols, hinges on the stability of their conjugate bases. When an acid donates a proton (H+H^+), it forms a conjugate base. The more stable this conjugate base is, the more readily the acid will donate its proton, and thus, the stronger the acid.

In the case of phenols, the acidity arises from the resonance stabilization of the phenoxide ion (the conjugate base). Any factor that stabilizes this negative charge on the oxygen atom will increase acidity, while any factor that destabilizes it will decrease acidity.

Electron-releasing groups (ERGs) or electron-donating groups (EDGs) push electron density towards the benzene ring. This increased electron density is then delocalized onto the oxygen atom of the phenoxide ion. By intensifying the negative charge on the oxygen, ERGs destabilize the conjugate base, making the parent phenol less acidic. Conversely, electron-withdrawing groups (EWGs) pull electron density away from the benzene ring, thereby stabilizing the negative charge on the oxygen of the phenoxide ion, making the parent phenol more acidic.

  1. Analyze Assertion (A): "Phenol is less acidic than 4-methylphenol."
    • Let's consider phenol (C6H5OHC_6H_5OH) and 4-methylphenol (CH3−C6H4−OHCH_3-C_6H_4-OH).
    • The acidity of these compounds depends on the stability of their respective conjugate bases: the phenoxide ion and the 4-methylphenoxide ion.
    • In 4-methylphenol, a methyl group (CH3CH_3) is present at the para position. The methyl group is an electron-releasing group (ERG) due to both its positive inductive effect (+I+I effect) and hyperconjugation.
    • This electron-releasing effect of the methyl group pushes electron density into the benzene ring. This increased electron density is then delocalized onto the oxygen atom of the 4-methylphenoxide ion.
    • By increasing the electron density on the already negatively charged oxygen, the methyl group destabilizes the 4-methylphenoxide ion compared to the phenoxide ion (which lacks this additional electron-donating group).
    • Since the conjugate base of 4-methylphenol is less stable, 4-methylphenol is less acidic than phenol.
    • Therefore, phenol is more acidic than 4-methylphenol.
    • The assertion states "Phenol is less acidic than 4-methylphenol," which is the opposite of our finding.
    • Thus, Assertion (A) is false. …

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