Question

An organic compound A on treatment with ethanol yields a carboxylic acid B and a neutral compound C. On hydrolysis, C produces B an another compound D . D on oxidation produces B, which on heating with Ca(OH)2 gives E (C3H6O). E forms 2,4-dinitrophenylhydrazone derivative but does not show Fehling test. Identify A to E. Please Help.

Answer 1

Well, the Fehling tests tells you that its not a ketone, but you have an aldehyde compound. So that's one clue.

Answer 2

I think that what it means by a derivative of the molecule is that it was reacted with an aldehyde, since it failed the fehling test.