Solutions_Manual_for_Organic_Chemistry_6th_Ed 220

Solutions_Manual_for_Organic_Chemistry_6th_Ed 220 - 10-9...

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10-9 continued Nitro group at position 2 :0: :0: Nitro group at position 3 :0: :0: Nitro group at position 4 :0: .. .. . . :0: :0: Nitro at position 2 delocalizes negative charge. Nitro at position 3 cannot delocalize negative charge at position 2 or 4- no resonance stabilization. :0: Nitro at position 4 delocalizes negative charge. - .."N , . - :0'" + 0: Only when the nitro group is at one of the negative carbons will the nitro have a stabilizing effect (via resonance) . Thus, 2-nitrophenol and 4-nitrophenol are substantially more acidic than phenol itself, but 3- nitrophenol is only slightly more acidic than phenol (due to the inductive effect). 10-10 OR A (a) Structure A is a phenol because the OH is bonded to a benzene ring. As a phenol, it will be acidic enough to react with sodium hydroxide to generate a phenoxide ion that will be fairly soluble in water.
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