An organic compound (A) on treatment with ethyl alcoholives a carboxylic acid (B) and compound (C). Hydrolysis of (C) under acidified conditions gives

Question

An organic compound (A) on treatment with ethyl alcohol gives a carboxylic acid (B) and compound (C). Hydrolysis of (C) under acidified conditions gives (B) and (D). Oxidation of (D) with KMnO₄ also gives (B). (B) on heating with Ca(OH)₂ gives (E) having molecular formula C₃H₆O. (E) does not give Tollen’s test and does not reduce Fehling’s solution but forms a 2, 4-dinitrophenylhydrazone. Identify (A), (B), (C), (D) and (E).

Answer 1

E does not give Tollen’s reagent test and does not reduce Fehling’s solution as it is ketone.