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teh way of analysing these qsns is two fold:
A) how much of a chance is there for a H+ ion to be produced - this is higher if the H-neighboring atom electron cloud is highly distorted towards the neighboring atom - This happens if it is an electro-ve atom. more eletro-ve then the chance of H+ being produced is greater. In qsns of comparison u must see which of the compunds has this capacity
B) the second factore to see is - if it is just cyclic - does this structure obtained after losing H+ - does this destabilize the cyclic compound - as in will this kind of losing of H+ reult in the ring becoming unstable. If it does then in such a case losing of H+ has very little chance. However, if losing the H+ gives rise to a structure that is more stabilized than not losing H+, then losing it is favored.
In aromatic compounds and aslso in normal cyclic compounds you should see if losing the H+ gives rise to aromaticity. If it does, then teh aromatic structure will be more stable than the normal structure/. Hence aromatic structure will be favored and H+ will be lost easily. If however, losing H+ disturbs aromaticity and hence stability,. then losing H+ is not favored.
And in compounds with benzene ring, you must check whether losing such a H+ gives rise to greater chance of electron delocalization. If it does, then it is favored.However, with aromatic compounds several more factors also come in.
Hence, the general strategy is always to see
a) is there, firstly, a chance of losing H+
b) If the H+ is lost, is the obtained structure more/less stable than the given structure?
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