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.

Question

anonymous · Answer

I can't figure out what A is but here's how you do the rest....
Now E reacts with 2,4 DNP indicating it has a carbonyl group. It does not show fehling's test indicating it is a ketone The only ketone possible is acetone. So you know E is CH3 CO CH3 or acetone. Now you get acetone by decarboxylation and the only place available to decarboxylate is the terminal postion so you can say B is |dw:1329549065618:dw|