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What is more polar 4-nitrophenylaceto nitrile or -nitrophenylacetic acid?
Wiki User
∙ 8y ago
4-nitrophenol is more polar than phenol by the inductive effect. NO2 has a dipole that pulls electrons away from the oxygen on hydoxyl group, thus increasing the polarity between H+ and O-. It also makes phenol more acidic, as the phenol hydrogen can come off a lot more easier.
On a side note, the position of the nitro group also plays in polarity. When it is placed in the 3-position (meta), the nitro group can now participate in resonance with the benzene ring, whereas position 2+4 (ortho and para, respectively) can't break bonds to participate in resonance. Therefore, the polarity and acidity would increase in this manner:
phenol > 4-nitrophenol > 2-nitrophenol > 3-nitrophenol.
Wiki User
∙ 14y ago
Wiki User
∙ 9y agoThe first because of its bigger asymerticity
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