There are four organic acids below. Compare the acidities of four compounds and explain. 1. benzoic...

There are four organic acids below. Compare the acidities of four compounds and explain.

1. benzoic acid

2. 4-nitrophenol

3. 3-nitrophenol

4. 4-Methoxyphenol

Expert Solution

The most acidic amon these compounds is 1) Benzoic acid as it has free H⁺

the next most acidic compound will be 2) 4- nitrophenol followed by 3 nitrophenol and finally the 4- methoxyphenol

The reason for this is that in the phenolate anion we see the following resonance stabilization. The more the conjugate base is stabilized the stronger the acid.

So having a withdrawing group like nitro at the 4 position increases the stabilization of the phenolate and so it is a strong acid whereas in the case of a donating group like methoxy the stabilization reduces. Comparing the 4-nitrophenol with the 3-nitrophenol. Extra resonance stabilization is possible at the 4 position which does not happen at the 3 position.

So the final acidity comparision between the four is. benzoic acid is most acidic and 4-methoxyphenol is least acidic

benzoic acid> 4-nitrophenol> 3-nitrophenol>4-Methoxyphenol

queen_honey_blossom answered 2 years ago

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