Question

An organic compound A on treatment with acetic acid in the presence of sulphuric acid produces an ester B. A on mild oxidation gives C; C with 50% potassium hydroxide followed by acidification with dilute hydrochloric acid generates A and D: D with phosphorus pentachloride followed by reaction with ammonia gives E; E on dehydration produces hydrocyanic acid. Identify the compounds A, B, C, D and E.

Answer 1

 (i) A on mild oxidation gives C, which reacts with 50% KOH to produce A and D. Thus, C is an aldehyde having no α-H-atom (as it gives Cannizaro's reaction). Hence A is an alcohol.

(ii) D on reacting with PCl₅ followed with action of NH₃ gives E which on dehydration produces HCN.

(iii) Step (III) clearly suggests that :

(iv) A also reacts with acetic acid to form ester B.