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Dolbier HW Solutions 591 - 685 PHENOLS(d A cyano group is...

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( d ) A cyano group is strongly electron-withdrawing, and so 4-cyanophenol is a stronger acid than phenol. There is resonance stabilization of the 4-cyanophenoxide anion. ( e ) The 5-nitro group in 2,5-dinitrophenol is meta to the hydroxyl group and so does not stabilize the resulting anion as much as does an ortho or a para nitro group. 24.15 ( a ) The rate-determining step of ester hydrolysis in basic solution is formation of the tetrahedral intermediate. Because this intermediate is negatively charged, there will be a small effect favoring its for- mation when the aryl group bears an electron-withdrawing substituent. Furthermore, this in- termediate can either return to starting materials or proceed to products. The proportion of the tetrahedral intermediate that goes on to products increases as the leav- ing group ArO becomes less basic. This is strongly affected by substituents; electron-
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