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Chemistry LibreTexts

Solution to Exercise 7-4-3

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    43327
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    The order of acidity, going from left to right (with 1 being most acidic), is 2-1-4-3. The least acidic compound (second from the right) has no phenol group at all - aldehydes are not acidic. The most acidic compound (second from the left) is a phenol with an aldehyde in the 2 (ortho) position, and as a consequence the negative charge on the conjugate base can be delocalized to both oxygen atoms. In the compound with the aldehyde in the 3 (meta) position, there is an electron-withdrawing inductive effect, but NOT a resonance effect (the negative charge on the cannot be delocalized to the aldehyde oxygen).