Explain why is ortho nitrophenol more acidic than ortho methoxyphenol?
Question
Explain why is ortho nitrophenol more acidic than ortho methoxyphenol?
Solution
Ortho nitrophenol is more acidic than ortho methoxyphenol due to the electron withdrawing nature of the nitro group. Here's a step-by-step explanation:
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Both ortho nitrophenol and ortho methoxyphenol have a hydroxyl group (-OH) attached to the benzene ring. This group can lose a proton (H+) to act as an acid.
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The acidity of these compounds depends on the stability of the negative ion (anion) formed after the loss of the proton. The more stable the anion, the more acidic the compound.
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In ortho nitrophenol, the nitro group (-NO2) is an electron withdrawing group. It pulls electron density away from the benzene ring and the hydroxyl group. This makes the loss of the proton easier and stabilizes the anion formed by delocalizing the negative charge.
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In contrast, in ortho methoxyphenol, the methoxy group (-OCH3) is an electron donating group. It pushes electron density towards the benzene ring and the hydroxyl group. This makes the loss of the proton harder and the anion formed is less stable.
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Therefore, due to the electron withdrawing nature of the nitro group, ortho nitrophenol is more acidic than ortho methoxyphenol.
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