(a) An organic compound with the molecular formula C_9 H_(10)O forms 2, 4-DNP derivative, reduces Tollen's reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1,2-benzenedicarboxylic acid. Identify the compound. (B ) Arrange the following compounds in the increasing order of their reactivity in nucleophilic addition reaction : Ethanal, propanal, propanone, butanone. (c) Although p-hydroxybenzoic acid is less acidic than benzoic acid, ortho hydroxybenzoic acid is about 15 times more acidic than benzoic acid. Explain.

(a) An organic compound with the molecular formula C_9 H_(10)O forms 2

1.	(a) An organic compound with the molecular formula C_9 H_(10)O forms 2, 4-DNP derivative, reduces Tollen's reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives 1,2-benzenedicarboxylic acid. Identify the compound. (B ) Arrange the following compounds in the increasing order of their reactivity in nucleophilic addition reaction : Ethanal, propanal, propanone, butanone. (c) Although p-hydroxybenzoic acid is less acidic than benzoic acid, ortho hydroxybenzoic acid is about 15 times more acidic than benzoic acid. Explain.
Answer» SOLUTION :Thegivencompoundforms2,4-DNPderivationtherefore, it ISAN aldehydeor ketone. Sinceit reduceTollen.sreagentit mustbe analdehyde . The compoundundergoescannizzaro.sreactionsoitdoes notcontaina- hydrogen.onvigorousoxidation, itisgives1,2- benzenedicarboxylicacid,ti meansthatit must becontainingalkylgroupat -2- positionwithrespectto CHOgroupon thebenzenring (b) Butanone< propanone< propanal < ehtanal (c )-OHgroupis electron relasinggroupand thereforeitincreases the negativechargeon theanion.As ARESULT , p- hydroxybenzoicacid islessacidicthanbenzoicacidhowever. o - hydrogxybenzoicacid ismore acidicthenbenzoicacidethancesacidityof o-isomeris duetoveryeffectiveintramolecularhydrogenbondingin thecarbonylateion. As a result , o- hydroxybenzoateionstabilizedto a greatextentand THEREFORE, it makeso- isomermoreacidic