Question

An organic compound A with the molecular formula C₇H₈ on oxidation by chromyl chloride in the presence of CCl₄ 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 soda-lime gives a hydrocarbon E. Below 60°C, concentrated nitric acid reacts with E in the presence of concentrated sulphuric acid forming a compound F. Identify the compounds A, B, C, D, E, and F.

Answer 1

\[\ce{A -> \underset{\text{(Toluene)}}{C6H5CH3},  B-> \underset{\text{(Benzaldehyde)}}{C6CH5CHO},    C->\underset{\text{(Benzyl alcohol)}}{C6H5CH2OH}}\]

\[\ce{D -> \underset{\text{(Benzoic acid)}}{C6H5COOH},   E->\underset{\text{(Benzene)}}{C6H6},    F-> \underset{\text{(Nitrobenzene)}}{C6H5NO2}}\]