Question

An organic compound with molecular formula C7H80 on oxidation gives compound B which can reduce tollen's reagent. B on reaction with conc. NaOH gives compound C and D. Identify the compounds and write the reactions involved

Answer 1

Explanation:

An organic compound A with molecular formula C

7

H

8

on oxidation by chromylchloride in the presence of CCl

4

gives a compound B which gives positive tollen's test. The compound B on treatment with NaOH followed by acid hydrolysis gives two products C and D. C on oxidation gives B which on further oxidation gives D. The compound D on distillation with sodalime gives a hydrocarbon E. Below 60

o

C, concentrated nitric acid reacts with E in the presence of concentrated sulphuric acid forming a compound F.