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Why picric acid is more acidic than 3,5 - dinitrophenol ? There are two intramolecular hydrogen bonding in picric acid that restrict it to donate H+ and hence it must not be aciduc at all . But i found that picric acid is more acidic just cause it form stable conjugate base.....but it should not release H+ in the first place .....plz help

Why picric acid is more acidic than 3,5 - dinitrophenol ? There are two intramolecular hydrogen bonding in picric acid that restrict it to donate H+ and hence it must not be aciduc at all . But i found that picric acid is more acidic just cause it form stable conjugate base.....but it should not release H+ in the first place .....plz help

Grade:12

2 Answers

Rohan Goyal
37 Points
5 years ago
Picric acid is one of the strongest acid in organic chemistry. It is called as acid because it releases H positive  ions when it is ionized. 
You might be thinking what so special in it. Well as we all know acids donate protons ( H positive ions as they lack any electron and neutron, just have only one proton), in organic chemistry, H+ ion donating depends upon various factors. One such is electron withdrawing effect of NO2 group attached to ring of picric acid. This electron withdrawing effect decreases electron density over oxygen atom, resulting in easy bond breakage of O-H bond. This attributes to release of large no of protons during its ionization. Also stability of conjugate base is also essential. 
whereas in di nitro... only two groups contribute in -I effect.
i hope you get my point. best of luck for ur studies.
IMPORTANT – Never confuse in comparing acidic and basic strenths of compounds
Rohan Goyal
37 Points
5 years ago
always compare acidic and basic strength by comparing stabilities of conjugate acid-base pair... ALWAYS.. Never get confused.

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