Compound A is acidic in reaction , having the molecular formula , C_(4) H_(8) O_(3) , is oxidized with mild oxidizing agents to give B which is unstable , syrupy substance , it easily produces , C , C_(3) H_(6) O and carbon dioxide . On heating A alone yields D , C_(4) H_(6) O_(2) an acid neutralization equivalent of 104 . what are A , B, C and D ? Give their structural formulae too.

Compound A is acidic in reaction , having the molecular formula , C_(4

1.	Compound A is acidic in reaction , having the molecular formula , C_(4) H_(8) O_(3) , is oxidized with mild oxidizing agents to give B which is unstable , syrupy substance , it easily produces , C , C_(3) H_(6) O and carbon dioxide . On heating A alone yields D , C_(4) H_(6) O_(2) an acid neutralization equivalent of 104 . what are A , B, C and D ? Give their structural formulae too.
Answer» Solution :Compound A has molecular formula `C_(4) H_(8) O_(3)` as it ACIDIC in reaction . So , it should have -COOH group .The REMAINING group `C_(3) H_(7) O` contains oxygen . The product D , having formula `C_(3) H_(5) COOH` , an unsaturated acid obtained by heating compound A `beta` - hydroxy substituted acids YIELD substituted acids on heating. Hence , A should be `beta` - hydroxy substitued acid i.e. `(A) =CH_(3)- overset(OH)overset(\|)(C)H - CH_(2) - COOH` (A) on oxidation with mild oxidizing reagents will give `CH_(3) - overset(OH)overset(\|)(C)H - CH_(2) - COOH overset("Oxidation")(to) CH_(2) - overset(O)overset(\|\|)(C) - CH_(2) - COOH` B is keto substituted acid , hence , on further decomposition it will ELIMINATE `CO_(2)` to give `CH_(3) - overset(O)overset(\|\|)(C)- CH_(2) - COOHoverset(-CO_(2))(to) underset((C) "ACETONE")(CH_(3) COCH_(3))`